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Chemical reaction
The aldol reaction (aldol addition) is a reaction in organic chemistry that combines two carbonyl compounds (e.g. aldehydes or ketones) to form a new
Aldol_reaction
Type of chemical reaction
An aldol condensation is a condensation reaction in organic chemistry in which two carbonyl moieties (of aldehydes or ketones) react to form a β-hydroxyaldehyde
Aldol_condensation
Organic compound of the form R–CH(OH)–CHR–C(=O)–R
In organic chemistry, an aldol is a structure consisting of a hydroxy group (-OH) two carbons away from either an aldehyde or a ketone. The name combines
Aldol
Organic reaction between a silyl enol ether and an aldehyde or formate
In organic chemistry, the Mukaiyama aldol addition is an organic reaction and a type of aldol reaction between a silyl enol ether (R2C=CR−O−Si(CH3)3)
Mukaiyama_aldol_addition
Chemical reaction in organic chemistry
β-unsaturated ketone in a cyclohexane ring by a Michael addition followed by an aldol condensation. This procedure is one of the key methods to form fused ring
Robinson_annulation
Topics referred to by the same term
Look up Aldo or aldo in Wiktionary, the free dictionary. Aldo may refer to: Aldo (given name), male given name Aldo (footballer, born 1957) Aldo (footballer
Aldo
Chemical compound
meprobamate. It is prepared by aldol condensation of propionaldehyde followed by dehydration and hydrogenation of the aldol product. Kohlpaintner, Christian;
2-Methylpentanal
Russian Romantic composer, physician, and chemist (1833–1887)
demonstrate nucleophilic substitution, as well as being the co-discoverer of the aldol reaction. Borodin was a promoter of education in Russia and founded the
Alexander_Borodin
Structural analog of a ketone with selenium replacing oxygen
oxazolidineselones can be used for stereoselective control of aldol reactions, analogous to the Evans aldol reaction that uses oxazolidinones, which allows 77Se-NMR
Selone
Reaction sequence in organic chemistry
The Stork enamine alkylation involves the addition of an enamine to a Michael acceptor (e.g., an α,β -unsaturated carbonyl compound) or other electrophile
Stork_enamine_alkylation
Organic anion formed by deprotonating a carbonyl (>C=O) compound
presence of Lewis acids (the Mukaiyama aldol reaction): Other important electrophiles are aldehydes/ketones (the aldol reaction) and Michael acceptors. Enamine
Enolate
Functional group of organic compounds
maleic acid. Unsaturated carbonyls can be prepared in the laboratory in an aldol reaction and in the Perkin reaction. α,β-Unsaturated carbonyl compounds
Α,β-Unsaturated carbonyl compound
Α,β-Unsaturated_carbonyl_compound
Michael/aldol reaction (or domino Michael/aldol reaction) is a consecutive series of reactions composed of either Michael addition reactions or aldol reactions
Multiple Michael/aldol reaction
Multiple_Michael/aldol_reaction
Chemical reaction
species with a C=C bond) and the resulting cyclobutane ring undergoes a retro-aldol reaction to yield a 1,5-diketone: The net effect is to add the two carbon
DeMayo_reaction
Reaction in organic chemistry
reactions in organic chemistry are a family of proline-catalysed asymmetric aldol reactions. In the 1970s, two research groups discovered (and published)
Proline-catalyzed aldol reactions
Proline-catalyzed_aldol_reactions
Index of chemical compounds with the same name
protein synthesis inhibitor antibiotics and the Evans chiral auxiliaries for aldol reactions. Cycloserine is an antibiotic based on the 3-isoxazolidone parent
Oxazolidinone
Chemical compound
hydrogen halides in solvents, and its preparation is used as an example of the aldol condensation in organic chemistry teaching labs. Dicinnamalacetone (specifically
Dicinnamalacetone
Type of aldol condensation reaction
and the nucleophile in an aldol condensation. It is also called a symmetrical aldol condensation as opposed to a mixed aldol condensation in which the
Self-condensation
Chemical group (–OSO2CF3) or anion (charge –1)
triflate is used in such reactions as aldol reactions and Diels–Alder reactions. An example is the Mukaiyama aldol addition reaction between benzaldehyde
Triflate
Concept in organic chemistry
radical or cationic pathways. Baldwin also noted a further constraint on aldol cyclizations. Two new descriptors need to be defined: enolendo and enolexo
Baldwin's_rules
The Aldol–Tishchenko reaction is a tandem reaction involving an aldol reaction and a Tishchenko reaction. In organic synthesis, it is a method to convert
Aldol–Tishchenko_reaction
Organic compound with the formula CH3CH(OH)CH2CHO
(acetaldol, aldol) is an organic compound with the formula CH3CH(OH)CH2CHO and the structure H3C−CH(OH)−CH2−CH=O. It is classified as an aldol (R−CH(OH)−CHR'−C(=O)−R")
3-Hydroxybutanal
Chemical reaction involving the formation of sugars from formaldehyde
metal such as calcium. The intermediary steps taking place are aldol reactions, reverse aldol reactions, and aldose-ketose isomerizations. Intermediates are
Formose_reaction
Chemistry
other bonds have been formed using DKR and are highly successful. The aldol reaction has been extensively researched primarily because of the inherent
Dynamic kinetic resolution in asymmetric synthesis
Dynamic_kinetic_resolution_in_asymmetric_synthesis
Japanese chemist (1927–2018)
as the Mitsunobu reaction. The aldol reaction is an essential tool for synthetic chemists. At its simplest, the aldol reaction involves two carbonyl compounds
Teruaki_Mukaiyama
Named reaction in organic chemistry
lacking an α-hydrogen. It can be considered as a specific variation of the aldol condensation. This reaction is named after two of its pioneering investigators
Claisen–Schmidt_condensation
Chemical compound
C9H14O + CaCO3 It is now typically obtained by the acid-catalysed twofold aldol condensation of three molecules of acetone. Mesityl oxide is obtained as
Phorone
Named reaction for synthesis of coumarins
generate the new ring. The final step is a dehydration, as seen following an aldol condensation. It was discovered by the German chemist Hans von Pechmann
Pechmann_condensation
Organic chemical reaction
named after German chemist Emil Knoevenagel. It is a modification of the aldol condensation. A Knoevenagel condensation is a nucleophilic addition of an
Knoevenagel_condensation
Protein family
generally, to an enzyme that performs an aldol reaction (creating an aldol) or its reverse (cleaving an aldol), such as Sialic acid aldolase, which forms
Fructose-bisphosphate aldolase
Fructose-bisphosphate_aldolase
Stereogenic group placed on a molecule to encourage stereoselectivity in reactions
auxiliaries for one asymmetric alkylation reaction and four asymmetric aldol reactions, setting the absolute stereochemistry of nine stereocenters. Cytovaricin
Chiral_auxiliary
Chemical compound
colorless, volatile liquid with a honey-like odor. It is prepared by the aldol condensation of acetone to give diacetone alcohol, which readily dehydrates
Mesityl_oxide
Steric effect from the spatial arrangement of methyl groups in n-pentane
is known as 1,3 allylic strain or (A1,3 strain). For instance in certain aldol adducts with 2,6-disubstituted aryl groups the molecular geometry has the
Pentane_interference
Chemical compound
asymmetric synthesis for example in the formation of boron enolates in the aldol reaction. Organic Syntheses, Coll. Vol. 8, p.339 (1993); Vol. 68, p.83 (1990)
Dibutylboron trifluoromethanesulfonate
Dibutylboron_trifluoromethanesulfonate
Chemical compound
synthesis, particularly in carbon–carbon bond-forming reactions such as the aldol reactions, Diels–Alder cycloaddition, and Friedel–Crafts acylations. It
Yttrium_triflate
Chemical compound
benzaldehyde is produced from cinnamaldehyde obtained from cassia oil by the retro-aldol reaction: the cinnamaldehyde is heated in an aqueous/alcoholic solution
Benzaldehyde
Method of synthesizing supramolecular assemblies
formation of new covalent bonds. Some examples include Diels–Alder and aldol reactions. In some cases, a reaction can pertain to both categories. For
Dynamic_covalent_chemistry
Charged chemical group of the form >CO–
exploited to carry out highly diastereoselective and enantioselective acetate aldol addition reactions. The oxocarbenium ion is used as an electrophile in the
Oxocarbenium
including the Jung "non-aldol aldol" protocol, an alternate method for obtaining aldol products without using the classical aldol reaction. He has also
Michael_E._Jung
Functional group made of a ketone (>C=O) and hydroxyl (–OH) group on nearby carbons
positive Fehling's test. Beta-hydroxy ketones are a type of aldol. They are commonly formed by an aldol reaction between two carbonyl compounds. A simple example
Hydroxy_ketone
Class of organic chemistry reactions
development of related reactions including the Michael addition, asymmetric aldol reaction, and the Mannich reaction. This reaction has likewise been used
Proline_organocatalysis
Chemical compound
fresheners. It has a spicy cinnamon/cassia aroma. Synthetic routes include an aldol-like condensation of benzaldehyde with acetonitrile under alkaline conditions
Cinnamonitrile
Chemical compound
produced by cooking or drying of the ginger root, which causes a reverse aldol reaction on gingerol. Zingerone was first isolated from the ginger root
Zingerone
Chemical reaction
aldehyde. The Aldol product is then deprotonated forming another enolate followed by the elimination of water in an E1cB dehydration reaction. Aldol reactions
E1cB-elimination_reaction
Chemical compound
(CH3)2CHCHO → HOCH2(CH3)2CCHO The compound is a rare example of a distillable aldol (3-hydroxyaldehyde). Upon standing, it dimerizes reversibly to the dioxane
Hydroxypivaldehyde
Organic compound containing the functional group R–CH=O
the aldol reaction, the metal enolates of ketones, esters, amides, and carboxylic acids add to aldehydes to form β-hydroxycarbonyl compounds (aldols). Acid
Aldehyde
Chemical compound
African Ginger species. Cooking ginger transforms gingerol via a reverse aldol reaction into zingerone, which is less pungent and has a spicy-sweet aroma
Gingerol
Compound with carbon to copper bonds
carbocupration/Mukaiyama aldol reaction sequence (as shown in the figure above) carbocupration favors the formation of the Z-aldol. Ethyl copper Yao, B.;
Organocopper_chemistry
Chemical reaction where molecules are combined and a small molecule is lost
variations of condensation reactions exist. Common examples include the aldol condensation and the Knoevenagel condensation, which both form water as
Condensation_reaction
Chemical reaction
development of the well-known Tishchenko reaction discovered in 1906. The Aldol–Tishchenko reaction provides another potential route to 1,3-diol monoester
Evans–Tishchenko_reaction
Chemical compound
nucleophilic. For this reason, dibenzyl ketone is frequently used in an aldol condensation reaction with benzil (a dicarbonyl) and base to create
Dibenzyl_ketone
American organic chemist (1941–2022)
biologically active molecules. Among his best-known works is the development of aldol reaction methodology (for example, Evans' acyl oxazolidinone method). Evans
David_A._Evans
Type of strain energy in organic chemistry
oxazolidinone. There is another aspect of aldol reaction that is influenced by the allylic strain. On the second aldol reaction, the product which is a 1,3
Allylic_strain
Organic reaction in which indigo is prepared from 2-nitrobenzaldehyde and acetone
procedure is not used at industrial scale. The reaction is classified as an aldol condensation. As a practical route to indigo, this method was displaced
Baeyer–Drewsen indigo synthesis
Baeyer–Drewsen_indigo_synthesis
Chemical compound (CH2)3(CHO)2
equilibrate with cyclic hemiacetal. Monomeric glutaraldehyde polymerizes by aldol condensation and Michael reactions yielding alpha, beta-unsaturated poly-glutaraldehyde
Glutaraldehyde
Chemical compound
use of no NAD. The mechanism of ring closure is complex, but involves an aldol condensation at C-2 and C-7. Metabolic engineering has improved production
3-Deoxy-D-arabino-heptulosonic acid 7-phosphate
3-Deoxy-D-arabino-heptulosonic_acid_7-phosphate
Interconnected biochemical reactions releasing energy
Reaction type Substrates Enzyme Products Comment 0 / 10 Aldol condensation Oxaloacetate + Acetyl CoA + H2O Citrate synthase Citrate + CoA-SH irreversible
Citric_acid_cycle
Chemical compound
An example of the scientific use of scandium triflate is the Mukaiyama aldol addition reaction between benzaldehyde and the silyl enol ether of cyclohexanone
Scandium(III) trifluoromethanesulfonate
Scandium(III)_trifluoromethanesulfonate
Organic redox reaction in chemistry
primary alcohols are seldom oxidized by this method due to the competing aldol condensation of aldehyde products. The Oppenauer oxidation is still used
Oppenauer_oxidation
Chemical compound
well as Aldol condensation. Several examples are shown below: Elimination: Epimerization of penicillin derivatives, catalyzed by DBN: Aldol condensation:
1,5-Diazabicyclo(4.3.0)non-5-ene
1,5-Diazabicyclo(4.3.0)non-5-ene
Organic chemical compound
prochiral. It is used primarily as a source of the "CH3C+H(OH)" synthon in aldol reactions and related condensation reactions. Grignard reagents and organolithium
Acetaldehyde
Chemical compound
oxidation of 4-tert-butyltoluene on greater than 10,000 ton per year scale. Aldol condensation with either propionaldehyde or acetaldehyde, followed by hydrogenation
4-tert-Butylbenzaldehyde
Use of metal-based Lewis acids to catalyze organic reactions
catalyzed by Lewis acids. Examples include the Friedel-Crafts reaction, the aldol reaction, and various pericyclic processes that proceed slowly at room temperature
Lewis_acid_catalysis
Group of isomers
oxide as a basic heterogeneous catalyst and serves as an example of an aldol condensation followed by a rearrangement reaction. The nucleophilic addition
Ionone
Chemical reaction
Typical reactions catalyzed by proton transfer are esterifications and aldol reactions. In these reactions, the conjugate acid of the carbonyl group
Acid_catalysis
Class of chiral ligands
twisted square planar intermediate. Enantioselectivity is observed for aldol-type reactions, Mannich-type reactions, ene reaction, Michael addition,
Bisoxazoline_ligand
Chemical compound
nucleophiles SR, OR, NR2, alkyl and aryl to give 7 . A one- or two-fold aldol condensation of N-acetylated 2,5-DKP 8 gives access to 3-dehydro-2,5-diketopiperazines
2,5-Diketopiperazine
American chemist
the inductive effect of nitrogen on the dehydration of the intermediate aldols polymerization of alpha diolefins with metal alkyl coordination catalysts (1957)
John_Kenneth_Stille
Transmission of electronic effects through a system of conjugated chemical bonds
to the carbonyl of the methyl ketone. In a vinylogous variation of the aldol reaction, an electrophile is attacked by a nucleophilic vinylogous enolate
Vinylogy
Chemical compound
process using acetone as the starting material. Self-condensation, a type of aldol reaction, produces diacetone alcohol, which readily dehydrates to give
Methyl_isobutyl_ketone
Organic reaction developed by William Henry Perkin
β-unsaturated aromatic acid or α-substituted β-aryl acrylic acid by the aldol condensation of an aromatic aldehyde and an acid anhydride, in the presence
Perkin_reaction
Chemical ring forming reaction
bond. These two steps are similar to a base-catalyzed aldol reaction. The oxygen anion in this aldol-like product then SN2 attacks on the formerly-nucleophilic
Darzens_reaction
Chemical reaction
forming reactions in organic chemistry, including the aldol reaction, Henry reaction (nitro-aldol reaction) and Mannich reaction. Although extensive research
Nitro-Mannich_reaction
Chemical compound
odorants. Several synthetic routes exist but the most common is a crossed-aldol condensation between piperonal (heliotropin) and propanal followed by selective
Helional
Chemical reaction
carbonyl compound is prepared in situ from two carbonyl compounds (via an Aldol condensation), the reaction is known as the Beyer method for quinolines
Doebner–Miller_reaction
Chemical compound
metathesis: A more recent enantioselective synthesis involves an intramolecular aldol addition/dehydration reaction of a macrocyclic diketone. Isotopologs of
Muscone
Chemical compound
mixture of 1,3,5- and 1,2,4-trimethylbenzenes. Trimerization of acetone via aldol condensation, which is catalyzed and dehydrated by sulfuric acid is another
Mesitylene
Chemical element with atomic number 22 (Ti)
used in organic chemistry as a Lewis acid, for example in the Mukaiyama aldol condensation. In the van Arkel–de Boer process, titanium tetraiodide (TiI4)
Titanium
Most abundant structural protein in animals
tropocollagen molecules form collagen fibrils, via covalent cross-linking (aldol reaction) by lysyl oxidase which links hydroxylysine and lysine residues
Collagen
Chemical compound
related compounds such as cinnamyl alcohol. An early synthesis involved the aldol condensation of benzaldehyde and acetaldehyde. Cinnamaldehyde can also be
Cinnamaldehyde
Organic reaction
formed 4. The resulting zinc alkoxide is also less susceptible to retro-aldol cleavage. Acid workup 5,6 removes zinc to yield zinc(II) salts and a β-hydroxy-ester
Reformatsky_reaction
Chemical compound
act as strong nucleophiles. It thus serves as a catalyst for Mukaiyama aldol reactions and group-transfer chain-growth polymerization reactions. As a
Tris(2,4,6-trimethoxyphenyl)phosphine
Tris(2,4,6-trimethoxyphenyl)phosphine
French chemist (1817–1884)
sodium, and for his discoveries of ethylamine, ethylene glycol, and the aldol reaction. Wurtz was also an influential writer and educator. Adolphe Wurtz
Charles_Adolphe_Wurtz
Organic chemistry reaction
of Aldol reaction and a tandem reaction. In a reaction between the ketone 3-pentanone and the aldehyde benzaldehyde catalyzed by base the bis Aldol adduct
Japp–Maitland_condensation
Chemical compound
the detergent industry since the 1930s. 2-Ethylhexanal is synthesized by aldol condensation of two equivalents of butyraldehyde followed by hydrogenation
2-Ethylhexanal
Metabolic pathway
oxaloacetate 2-methylcitrate Propionyl-CoA synthase and methylcitrate synthase Aldol condensation Propinate is first activated to propionyl-CoA by propionyl-CoA
Methylcitrate_cycle
Chemical compound
include overoxidation to the corresponding dicarbonyl or intermolecular aldol reaction of the starting material. Procedures to prevent side reactions
MoOPH
Liquid mixture used to maintain low temperatures
A typical experimental setup for an aldol reaction. Both flasks are submerged in a dry ice/acetone cooling bath (−78 °C) the temperature of which is being
Cooling_bath
Chemical reaction
carbonyl compound 1 and carbonyl compound 2 react in a rate-limiting step to aldol adduct 3. This intermediate loses water in an elimination reaction to unsaturated
Friedländer_synthesis
Transition metal carbene complex
equivalent structure such as transesterification, Michael addition, and aldol reaction. The Cr(CO)5 moiety is a strong electron withdrawing group making
Fischer_carbene
Chemical compound
exhibits the reactions characteristic of alkyl aldehydes, e.g. hydrogenation, aldol condensations, oxidations, etc. It is the simplest aldehyde with a prochiral
Propionaldehyde
Chemical reaction
the aldol reaction that had been discovered 23 years prior that couples two carbonyl compounds to form β-hydroxy carbonyl compounds known as "aldols" (aldehyde
Henry_reaction
Chemical compound
germacrene A hydroxylase, a cytochrome P450 enzyme. Oxidation of alcohol to aldol, via -germacrene A hydroxylase. Hydroxylation of alcohol to carboxyl group
Absinthin
Inorganic salt: MgCl2 and its hydrates
production of polypropylene. Magnesium chloride is also a Lewis acid catalyst in aldol reactions. Magnesium chloride is used for low-temperature de-icing of highways
Magnesium_chloride
Large biological molecule that acts as a catalyst
Zanghellini A, et al. (March 2008). "De novo computational design of retro-aldol enzymes". Science. 319 (5868): 1387–1391. Bibcode:2008Sci...319.1387J. doi:10
Enzyme
Organic compound (H–CHO); simplest aldehyde
small aldehydes (which need specific conditions to oligomerize through aldol condensation) oligomerizes spontaneously at a common state. The trimer 1
Formaldehyde
Modified aldol tandem reaction is a sequential chemical transformation that combines aldol reaction with other chemical reactions that generate enolates
Modified aldol tandem reaction
Modified_aldol_tandem_reaction
Chemical compound
alkali metal enolates and ZnCl2, provide control of stereochemistry in aldol condensation reactions. This control is attributed to chelation at the zinc
Zinc_chloride
Chemical element with atomic number 11 (Na)
weight. Sodium hydride is used as a base for various reactions (such as the aldol reaction) in organic chemistry. Metallic sodium is used mainly for the production
Sodium
Group of chemical compounds
step of adding two aldehydes together to obtain a larger aldehyde (the aldol condensation reaction) can precede the hydrogenation. Long chain oxo-alcohols
Oxo_alcohol
ALDOL
ALDOL
ALDOL
ALDOL
Girl/Female
Arabic, Muslim
Small Drizzling Cloud; Name of a Sahabiyyah (RA); Arabic Tribe
Girl/Female
Arabic, Gujarati, Hindu, Indian, Malayalam, Marathi, Sanskrit, Tamil, Telugu
Cheerful; Pleasant; Pretty
Boy/Male
Hindu, Indian
One with Fame
Boy/Male
Hindu, Indian, Tamil
Song
Girl/Female
Hindu
Forgiveness, Goddess of life, Maa Parvati
Girl/Female
American, Christian, Greek, Indian, Italian, Latin
Tender Touch; Grace
Boy/Male
Muslim
Security. Deposit.
Girl/Female
Arabic
Emerald; Precious Stone
Girl/Female
Hindu, Indian, Kannada, Marathi, Sanskrit, Sindhi, Tamil, Telugu
To be Bowed to
Girl/Female
Hindu
A small creeper
ALDOL
ALDOL
ALDOL
ALDOL
ALDOL