1-Phenyl-3-azabicyclo[3.1.0]hexan-2-one

Base Information

• Chemical Name: 1-Phenyl-3-azabicyclo[3.1.0]hexan-2-one
• CAS No.: 153275-06-0
• Molecular Formula: C₁₁H₁₁NO
• Molecular Weight: 173.214
• Hs Code.: 2933790002
• European Community (EC) Number: 691-147-5
• Nikkaji Number: J618.958J

Synonyms:1-phenyl-3-azabicyclo[3.1.0]hexan-2-one;153275-06-0;Cyclic milnacipran;starbld0006541;SCHEMBL2223486;CID 10997525

Chemical Property of 1-Phenyl-3-azabicyclo[3.1.0]hexan-2-one

Chemical Property:

• Melting Point: 85 - 88°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 173.084063974
• Heavy Atom Count: 13
• Complexity: 245

Purity/Quality:

≥95% ^*data from raw suppliers

1-phenyl-3-azabicyclo[3.1.0]hexan-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2C1(C(=O)NC2)C3=CC=CC=C3
• Uses: 1-Phenyl-3-azabicyclo[3.1.0]hexan-2-one is a milnacipran impurity. Milnacipran (M344600) is an antidepressant. A selective norepinephrine and serotonin reuptake inhibitor approved for the management of fibromyalgia.

Technology Process of 1-Phenyl-3-azabicyclo[3.1.0]hexan-2-one

There total 15 articles about 1-Phenyl-3-azabicyclo[3.1.0]hexan-2-one 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: 85.0%

(1R,5S)-1-phenyl-3-tosyl-3-azabicyclo[3.1.0]hexan-2-one → (1R,5S)-1-phenyl-3-azabicyclo[3.1.0]hexan-2-one (153275-06-0,810696-16-3)

Guidance literature:

With naphthalene; sodium; In 1,2-dimethoxyethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2021.152985

Reference yield: 80.0%

1-phenyl-3-tosyl-3-azabicyclo[3.1.0]hexan-2-one → 1-phenyl-3-azabicyclo<3.1.0>hexane-2-one (153275-06-0,810696-16-3)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 0 - 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c04268

Reference yield: 77.0%

methyl 2-aminomethyl-1-phenyl-1-cyclopropanecarboxylate hydrochloride → 1-phenyl-3-azabicyclo<3.1.0>hexane-2-one (153275-06-0,810696-16-3) + trans-2-aminomethyl-1-phenyl-1-cyclopropanecarboxylic acid

Guidance literature:

With sodium hydroxide; In methanol; at 70 ℃; for 0.333333h;

DOI:10.1002/prac.19953370112

upstream raw materials:

phenylacetonitrile

N-(but-3-en-1-yl)-4-methyl-N-(phenylethynyl)benzenesulfonamide

1-phenyl-3-(2-(trimethylsilyl)ethylsulfonyl)-3-aza-bicyclo[3.1.0]hexan-2-one

N-allyl-N-(phenylethynyl)-2-(trimethylsilyl)ethanesulfonamide

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