27300-27-2

Basic information

• Product Name: 2-acetyl-3,4,5,6-tetrahydropyridine,2-acetyl-3,4,5,6-tetrahydropyridine,1-(3,4,5,6-tetrahydro-2-pyridinyl)-Ethanone
• Synonyms: 2-acetyl-3,4,5,6-tetrahydropyridine,2-acetyl-3,4,5,6-tetrahydropyridine,1-(3,4,5,6-tetrahydro-2-pyridinyl)-Ethanone;Ethanone, 1-(3,4,5,6-tetrahydro-2-pyridinyl)-;1-(3,4,5,6-Tetrahydropyridine-2-yl)ethanone;2-Acetyl-3,4,5,6-tetrahydropyridine;1-(3,4,5,6-Tetrahydro-2-pyridinyl)ethanone;1-(3,4,5,6-Tetrahydropyridin-2-yl)ethanone;6-acetyl-2,3,4,5-tetrahydropyridine
• CAS NO: 27300-27-2
• Molecular Formula: C₇H₁₁NO
• Molecular Weight: 125.17
• Mol File: 27300-27-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 205℃
• Flash Point: 77℃
• Appearance: /
• Density: 1.06
• Vapor Pressure: 0.258mmHg at 25°C
• Refractive Index: 1.524
• PKA: 5.34±0.20(Predicted)
• CAS DataBase Reference: 2-acetyl-3,4,5,6-tetrahydropyridine,2-acetyl-3,4,5,6-tetrahydropyridine,1-(3,4,5,6-tetrahydro-2-pyridinyl)-Ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-acetyl-3,4,5,6-tetrahydropyridine,2-acetyl-3,4,5,6-tetrahydropyridine,1-(3,4,5,6-tetrahydro-2-pyridinyl)-Ethanone(27300-27-2)
• EPA Substance Registry System: 2-acetyl-3,4,5,6-tetrahydropyridine,2-acetyl-3,4,5,6-tetrahydropyridine,1-(3,4,5,6-tetrahydro-2-pyridinyl)-Ethanone(27300-27-2)

Safety Data

• Hazardous Substances Data: 27300-27-2(Hazardous Substances Data)

Usage

Definition

ChEBI: A tetrahydropyridine compound, bearing an acetyl group in the 6-position.

InChI:InChI=1/C7H11NO/c1-6(9)7-4-2-3-5-8-7/h2-5H2,1H3

Synthetic route

2-(1-hydroxy-2-oxo-1-propyl)pyrrolidine (208102-58-3) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
With phosphate buffer pH 9.0 at 100℃; for 0.5h; var. pH;	35%
With phosphate buffer pH 9.0 at 100℃; for 0.5h;

2-ethyl-3,4,5,6-tetrahydropyridine (1462-93-7) → 2-ethyl-5,6-dihydropyridine-3(4H)-one + 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Stage #1: 2-ethyl-3,4,5,6-tetrahydropyridine With tert.-butylhydroperoxide; selenium(IV) oxide In dichloromethane at 20℃; for 9h; Stage #2: With triphenylphosphine In dichloromethane at 0℃; for 12h;	A n/a B 25%

5,6-Bis-[(E)-isopropylimino]-heptylamine → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2) + 1-(1,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (25343-57-1)

Conditions	Yield
With oxalic acid In diethyl ether Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1-pyrroline (5724-81-2) + hydroxy-2-propanone (116-09-6) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
at 100℃; for 0.5h; phosphate buffer pH 7.0;

D-Glucose (2280-44-6) + L-proline (147-85-3) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2) + 1-(1,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (25343-57-1) + dimethylglyoxal (431-03-8) + 2-acetyl-1-pyrrolidine (85213-22-5) + 2-propanoyl-1-pyrroline + 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-propanone

Conditions	Yield
With phosphate buffer pH=7.0 In water at 160℃; for 0.166667h; flavor contribution and formation of intense roast-smelling odorants;

6-(1,1-dimethoxy)ethyl-2,3,4,5-tetrahydropyridine (163679-97-8) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2) + 1-(1,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (25343-57-1)

Conditions	Yield
With hydrogenchloride In dichloromethane for 24h;

Δ1-piperidein-6-carboxylate (3038-89-9) + 2-oxopropanal (78-98-8) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
In phosphate buffer at 20℃; for 2h; pH=7.2;

L-lysine (56-87-1) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: Streptomyces clavuligerus L-lysine ε-aminotransferase / aq. phosphate buffer / 1 h / 37 °C / pH 7.2 2: aq. phosphate buffer / 2 h / 20 °C / pH 7.2 View Scheme

(5-oxo-heptyl)-carbamic acid tert-butyl ester → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 14.7 g / TFA / CH2Cl2 / 24 h / 20 °C 2.1: TBHP; SeO2 / CH2Cl2 / 9 h / 20 °C 2.2: 25 percent / PPh3 / CH2Cl2 / 12 h / 0 °C View Scheme

2-oxopiperidine-1-carboxylic acid tert-butyl ester (85908-96-9) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: EtBr; TMEDA / tetrahydrofuran / 12 h / -78 °C 2.1: 14.7 g / TFA / CH2Cl2 / 24 h / 20 °C 3.1: TBHP; SeO2 / CH2Cl2 / 9 h / 20 °C 3.2: 25 percent / PPh3 / CH2Cl2 / 12 h / 0 °C View Scheme

7-chloro-2,2-dimethoxy-3-heptanone (163679-95-6) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / NaN3 / dimethylsulfoxide / 0.2 h / microwave irradiation 2: 95 percent / Ph3P / dimethylsulfoxide / 0.25 h / microwave irradiation 3: aq. HCl / CH2Cl2 / 24 h View Scheme
Multi-step reaction with 2 steps 1: 98 percent / Ph3P; NaN3 / dimethylsulfoxide / 0.3 h / microwave irradiation 2: aq. HCl / CH2Cl2 / 24 h View Scheme

N-(7-chloro-2,2-dimethoxy-3-heptylidene)isopropylamine (163679-86-5) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 82 percent / (COOH)2*2H2O / CH2Cl2; H2O / 1 h / Heating 2: 98 percent / NaN3 / dimethylsulfoxide / 0.2 h / microwave irradiation 3: 95 percent / Ph3P / dimethylsulfoxide / 0.25 h / microwave irradiation 4: aq. HCl / CH2Cl2 / 24 h View Scheme
Multi-step reaction with 3 steps 1: 82 percent / (COOH)2*2H2O / CH2Cl2; H2O / 1 h / Heating 2: 98 percent / Ph3P; NaN3 / dimethylsulfoxide / 0.3 h / microwave irradiation 3: aq. HCl / CH2Cl2 / 24 h View Scheme

7-Azido-2,2-dimethoxy-heptan-3-one (163679-96-7) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / Ph3P / dimethylsulfoxide / 0.25 h / microwave irradiation 2: aq. HCl / CH2Cl2 / 24 h View Scheme

N-Boc-prolinol (170491-63-1) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 49 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 2: 21 percent / 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, Et3N / 1.5 h / 80 °C 3: TFA / CH2Cl2 / 3 h / Ambient temperature 4: 35 percent / phosphate buffer pH 9.0 / 0.5 h / 100 °C / var. pH View Scheme

N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde (59378-82-4) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 21 percent / 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, Et3N / 1.5 h / 80 °C 2: TFA / CH2Cl2 / 3 h / Ambient temperature 3: 35 percent / phosphate buffer pH 9.0 / 0.5 h / 100 °C / var. pH View Scheme

2-hydroxymethylpyrrolidine (498-63-5) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 75 percent / Et3N / dioxane; H2O / 2 h / Ambient temperature 2: 49 percent / pyridinium chlorochromate / CH2Cl2 / 2.5 h / Ambient temperature 3: 21 percent / 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride, Et3N / 1.5 h / 80 °C 4: TFA / CH2Cl2 / 3 h / Ambient temperature 5: 35 percent / phosphate buffer pH 9.0 / 0.5 h / 100 °C / var. pH View Scheme

N-(tert-butoxycarbonyl)-2-(1-hydroxy-2-oxo-1-propyl)pyrrolidine (208102-59-4) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: TFA / CH2Cl2 / 3 h / Ambient temperature 2: 35 percent / phosphate buffer pH 9.0 / 0.5 h / 100 °C / var. pH View Scheme

Isopropyl-[1-{1-[(E)-isopropylimino]-ethyl}-5-(2,2,5,5-tetramethyl-[1,2,5]azadisilolidin-1-yl)-pent-(E)-ylidene]-amine → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3 / methanol / 3 h / Heating 2: aq. (COOH)2 / diethyl ether View Scheme

α-methyl-2-piperidylcarbinol (54160-32-6) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
With Dess-Martin periodane In dichloromethane Inert atmosphere;

(R,S)-2-aminoadipic acid (542-32-5) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: dmap; triethylamine / 24 h / 60 °C 2.1: sodium carbonate / water / 4 h / 20 °C 3.1: lithium aluminium tetrahydride / diethyl ether / 16 h / 0 °C / Inert atmosphere; Cooling with ice; Reflux 3.2: pH 3 / Acidic aqueous solution 4.1: Dess-Martin periodane / dichloromethane / Inert atmosphere View Scheme

6-acetylpiperidin-2-one (1260069-00-8) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / diethyl ether / 16 h / 0 °C / Inert atmosphere; Cooling with ice; Reflux 1.2: pH 3 / Acidic aqueous solution 2.1: Dess-Martin periodane / dichloromethane / Inert atmosphere View Scheme

N,6-diacetylpiperidin-2-one (1260068-99-2) → 1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium carbonate / water / 4 h / 20 °C 2.1: lithium aluminium tetrahydride / diethyl ether / 16 h / 0 °C / Inert atmosphere; Cooling with ice; Reflux 2.2: pH 3 / Acidic aqueous solution 3.1: Dess-Martin periodane / dichloromethane / Inert atmosphere View Scheme

1-(3,4,5,6-tetrahydro-2-pyridyl)-1-ethanone (27300-27-2) + zinc(II) iodide → ZnI2(6-acetyl-2,3,4,5-tetrahydropyridine)

Conditions	Yield
In diethyl ether at -20℃; for 0.0833333h; Inert atmosphere;

Upstream product

• 1462-93-7 2-ethyl-3,4,5,6-tetrahydropyridine 
• 1260068-99-2 N,6-diacetylpiperidin-2-one 
• 1260069-00-8 6-acetylpiperidin-2-one 
• 542-32-5 (R,S)-2-aminoadipic acid 
• 54160-32-6 α-methyl-2-piperidylcarbinol 
• 208102-59-4 N-(tert-butoxycarbonyl)-2-(1-hydroxy-2-oxo-1-propyl)pyrrolidine 
• 498-63-5 2-hydroxymethylpyrrolidine 
• 59378-82-4 N-(tert-butoxycarbonyl)pyrrolidine-2-carboxaldehyde 
• 170491-63-1 N-Boc-prolinol 
• 163679-96-7 7-Azido-2,2-dimethoxy-heptan-3-one 
• 163679-86-5 N-(7-chloro-2,2-dimethoxy-3-heptylidene)isopropylamine 
• 163679-95-6 7-chloro-2,2-dimethoxy-3-heptanone 
• 85908-96-9 2-oxopiperidine-1-carboxylic acid tert-butyl ester 
• 56-87-1 L-lysine 

Relevant articles and documents

Synthesis of 1-piperideine-6-carboxylic acid produced by L-lysine-ε-aminotransferase from the Streptomyces clavuligerus gene expressed in Escherichia coli

The gene (laf) encoding L-lysine ε-aminotransferase (LAT) in Streptomyces clavuligerus was cloned and expressed in Escherichia coli. Nucleotide sequence analysis of lat predicted a single open reading frame (ORF) of 1371 bp, encoding a polypeptide of 457 amino acids with calculated molecular mass of 49.89 kDa. S. clavuligerus LAT was grouped into aminotransferase subfamily II of a family on the basis of sequence homology. A model system composed of the recombinant LAT in phosphate buffer was set up to study the biosynthesis of 2-acetyltetrahydropyridine. Lysine was found to be transformed to 1-piperideine-6-carboxylic acid. 2-Acetyltetrahydropyridine was characterized from the mixture of 1-piperideine-6-carboxylic acid and methylglyoxal. For the first time, we demonstrated that the L-lysine ε-aminotransferase is responsible for the formation of 1-piperideine-6-carboxylic acid, which may react with methylglyoxal to generate the acylated N-heterocyclic odorant 2-acetyltetrahydropyridine.

METHOD FOR SYNTHESISING 2-ACETYL-1-PYRROLINE AND THE STABLE PRECURSOR THEREOF, OPTIONALLY ISOTOPICALLY MARKED

The present invention relates to a method for synthetizing a compound of the following formula (I): wherein R is a methyl or ethyl group, n is 1 or 2, and X is a CH2 or CD2 group, from a compound of the following formula (II): wherein R and n are as defined above, and also relates to a method for assaying the compounds of the formula (I) using a corresponding deuterated derivative as an internal reference, as well as to the use of ketal derivatives of compounds of the formula (I) as a stable precursor, in particular in a flavoring composition.

An efficient one-pot synthesis of pyrrolines and tetrahydropyridines from their chloro-precursors via in situ aza-Wittig reaction

A simple and efficient method for synthesizing pyrrolines and tetrahydropyridines via an intramolecular aza-Wittig reaction has been achieved by microwave irradiation of the corresponding chloro-alkane derivatives in the presence of tertiary phosphite and sodium azide. The in situ formation of the alkyl azides makes this a facile and safe method for aza-Wittig reactions.