116950-01-7

Basic information

• Product Name: (2S,3S,8AR)-2-PHENYL-3-HYDROXYMETHYL-8A-METHYL BICYCLIC LACTAM
• Synonyms: Oprea1_354110;[2S-(2ALPHA,3BETA,8ABETA)]-(+)-HEXAHYDRO-3-(HYDROXYMETHYL)-8A-METHYL-2-PHENYL-5H-OXAZOLO[3,2-A]PYRIDIN-5-ONE;(2S,3S,8AR)-2-PHENYL-3-HYDROXYMETHYL-8A-METHYL BICYCLIC LACTAM;hexahydro-3-(hydroxymethyl)-8A-methyl-2-phenyl-ox;HEXAHYDRO-3-(HYDROXYMETHYL)-8A-METHYL-2- PHENYL-OXAZOLO(3,2-A)PYRIDIN-5-ON, 98%;[2s-(2α,3β,8aβ)]-(+)-hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl-5h-oxazolo[3,2-a]pyridin-5-one;hexahydro-3-(hydroxymethyl)-8a-methyl-2-phenyl-oxazolo[3,2;3-(Hydroxymethyl)-8a-methyl-2-phenylhexahydro-5H-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS NO: 116950-01-7
• Molecular Formula: C₁₅H₁₉NO₃
• Molecular Weight: 261.32
• Product Categories: Chiral Building Blocks;Heterocyclic Building Blocks;Pyridines
• Mol File: 116950-01-7.mol

Chemical Properties

• Melting Point: 96-100 °C(lit.)
• Boiling Point: 449.5°Cat760mmHg
• Flash Point: 225.6°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 7.26E-09mmHg at 25°C
• Refractive Index: 1.6
• PKA: 14.27±0.10(Predicted)
• CAS DataBase Reference: (2S,3S,8AR)-2-PHENYL-3-HYDROXYMETHYL-8A-METHYL BICYCLIC LACTAM(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,8AR)-2-PHENYL-3-HYDROXYMETHYL-8A-METHYL BICYCLIC LACTAM(116950-01-7)
• EPA Substance Registry System: (2S,3S,8AR)-2-PHENYL-3-HYDROXYMETHYL-8A-METHYL BICYCLIC LACTAM(116950-01-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 116950-01-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3S,8AR)-2-PHENYL-3-HYDROXYMETHYL-8A-METHYL BICYCLIC LACTAM is used as a key intermediate in the synthesis of various pharmaceutical compounds due to its unique bicyclic lactam structure and chirality. Its potential as a precursor in the development of new drugs makes it a valuable asset in medicinal chemistry.
Used in Chemical Synthesis:
In the field of chemical synthesis, (2S,3S,8AR)-2-PHENYL-3-HYDROXYMETHYL-8A-METHYL BICYCLIC LACTAM serves as a versatile building block for creating complex organic molecules. Its specific functional groups and stereochemistry allow for targeted reactions and the formation of diverse chemical products.
Further research may reveal additional applications for (2S,3S,8AR)-2-PHENYL-3-HYDROXYMETHYL-8A-METHYL BICYCLIC LACTAM in other industries, such as materials science or agrochemicals, based on its structural and chiral properties.

InChI:InChI=1/C15H19NO3/c1-15-9-5-8-13(18)16(15)12(10-17)14(19-15)11-6-3-2-4-7-11/h2-4,6-7,12,14,17H,5,8-10H2,1H3/t12-,14-,15+/m0/s1

Upstream product

• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 3128-06-1 5-ketohexanoic acid 
• 105452-39-9 (1R,2S)-(+)-2-amino-1-phenyl-1,3-propanediol 

Downstream Products

• 35161-14-9 4,4-Diaethyl-2-cyclohexen-1-on 
• 122444-62-6 (R)-4-allyl-4-ethyl-2-cyclohexen-1-one 
• 122444-60-4 (1RS,4R)-4-ethyl-4-(3-hydroxypropyl)-2-cyclohexen-1-ol 
• 122444-63-7 (4R)-4-ethyl-4-(2-carboxyethyl)-2-cyclohexen-1-one 
• 122444-64-8 (4R)-4-ethyl-4-(2-carbamoylethyl)-2-cyclohexen-1-one 
• 122518-69-8 3-((R)-1-Ethyl-4-oxo-cyclohex-2-enyl)-propionic acid methyl ester 
• 122444-61-5 (2S,3S,6R,8aR)-6-allyl-6-ethyl-3-(hydroxymethyl)-8a-methyl-2-phenyl-5-oxo-2,3,6,7,8,8a-hexahydro-5H-oxazolo<3,2-a>pyridine 
• 112522-13-1 (R)-5-methyl-5-benzyl-2,6-decanedione 
• 116914-44-4 (2S,3S,6R,8aR)-6-Benzyl-5-butyl-3-hydroxymethyl-6,8a-dimethyl-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol 
• 112522-10-8 (2S,3S,6R,8aR)-6-Benzyl-3-hydroxymethyl-5,6,8a-trimethyl-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol 
• 112543-93-8 (R)-2-(n-propyl)-3,6-dimethyl-6-benzylcyclohexen-2-one 
• 112522-12-0 (R)-3-methyl-3-benzyl-2,6-heptadienone 
• 112522-14-2 (R)-6-Benzyl-3,6-dimethyl-cyclohex-2-enone 
• 112522-15-3 (R)-3,4-dimethyl-4-benzylcyclohexen-2-one 

Relevant articles and documents

AN ASYMMETRIC SYNTHESIS OF 4,4- AND 6,6-DIALKYLCYCLOHEXENONES AND 4,4- AND 5,5-DIALKYLCYCLOPENTENONES. APPLICATION TO THE TOTAL SYNTHESIS OF (-)-SILPHIPERFOL-6-ENE

Chiral amino alcohols have been transformed into bicyclic lactams 1 and 6 which, after metalation and alkylation, gave high diastereomeric ratios of 2,2-dialkyl quaternaly products, 29 and 12, respectively.Addition of organolithium reagents to the carbonyl of these lactams, followed by acidic cleavage, leads to enantiomerically pure cyclohex-2-enones and cyclopent-2-enones.This process was also applied to a key, chiral cyclopentenone 39, which was used by Curran, in racemic form, to prepare the angular triquinane, silphiperfol-6-ene.The total asymmetric synthesis was carried out in 6.6percent yield over nine steps.

An Asymmetric Synthesis of Chiral 4,4-Disubstituted Cyclohexenones in High Enantiomeric Purity

An efficient approach to the title compounds in > 95percent ee has been accomplished by metalation and alkylation of chiral bicyclic lactams derived from δ-keto acids and (1S,2S)-2-amino-1-phenyl-1,3-propanediol.