(1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane

Base Information

• Chemical Name: (1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane
• CAS No.: 174414-12-1
• Molecular Formula: C₁₂H₁₂O₂
• Molecular Weight: 188.226
• Mol file: 174414-12-1.mol

Synonyms:(1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane

Chemical Property of (1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane

There total 6 articles about (1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

(1S,2R)-1-phenyl-2-<(S)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide (171889-13-7) → (1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane (174414-12-1)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1016/0040-4039(95)02221-X

Reference yield:

(1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide (172016-00-1) → (1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane (174414-12-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / tetrahydrofuran / 2 h / -20 °C

2: 63 percent / aq. HCl (6 N) / methanol / 0.75 h / Heating

With hydrogenchloride; In tetrahydrofuran; methanol;

DOI:10.1021/jo9518056

Reference yield:

(1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide (172015-99-5) → (1S,4S,5R)-4-methyl-2-oxo-1-phenyl-3-oxabicyclo<3.1.0>hexane (174414-12-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1) CH₂Cl₂, -78 deg C, 2 h; 2) CH₂Cl₂, -78 deg C, 1 h

2: 93 percent / tetrahydrofuran / 2 h / -20 °C

3: 63 percent / aq. HCl (6 N) / methanol / 0.75 h / Heating

With hydrogenchloride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1021/jo9518056

upstream raw materials:

(1S,2R)-1-phenyl-2-<(S)-1-hydroxyethyl>-N,N-diethylcyclopropanecarboxamide

1-phenyl-3-oxa-bicyclo[3.1.0]hexan-2-one

(1 S,2 R)-N,N-diethyl-2-(hydroxymethyl)-1-phenylcyclopropane-carboxamide

(1S,2R)-2-Formyl-1-phenyl-cyclopropanecarboxylic acid diethylamide

Downstream raw materials:

(1S,2R)-2-((S)-1-Hydroxy-ethyl)-1-phenyl-cyclopropanecarboxylic acid methyl ester