Bicyclo[4.1.0]heptan-2-one

Base Information

• Chemical Name: Bicyclo[4.1.0]heptan-2-one
• CAS No.: 5771-58-4
• Molecular Formula: C7H10O
• Molecular Weight: 110.156
• Hs Code.: 2914299000
• NSC Number: 135954
• UNII: H4FJ5445LM
• DSSTox Substance ID: DTXSID50300325
• Nikkaji Number: J110.389J
• Mol file: 5771-58-4.mol

Synonyms:Bicyclo[4.1.0]heptan-2-one;5771-58-4;2-Norcaranone;NSC-135954;NSC135954;bicyclo[4.1.0]heptanone;SCHEMBL62747;Bicyclo[4.1.0]hept-2-one;H4FJ5445LM;DTXSID50300325;cis-Bicyclo[4.1.0]heptan-2-one;MFCD09866571;ZB1081;AKOS022504380;SB11967;AS-50657;CS-0049777;EN300-127294;P10813;A831568

Chemical Property of Bicyclo[4.1.0]heptan-2-one

Chemical Property:

• Vapor Pressure: 0.767mmHg at 25°C
• Boiling Point: 183.5°C at 760 mmHg
• Flash Point: 57.8°C
• PSA: 17.07000
• Density: 1.082g/cm³
• LogP: 1.37550
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 110.073164938
• Heavy Atom Count: 8
• Complexity: 128

Purity/Quality:

Bicyclo[4.1.0]heptan-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2CC2C(=O)C1
• Uses: Bicyclo[4.1.0]heptan-2-one (cas# 5771-58-4) is a product of a single step reaction between 2-Cyclohexen-1-one (cas# 930-68-7) and Trimethylsulfoxonium Iodide (cas# 1774-47-6). Bicyclo[4.1.0]heptan-2-one is used for biological research on anti-?inflammatory and analgesic potentials of Habenaria digitata.

Technology Process of Bicyclo[4.1.0]heptan-2-one

There total 3 articles about Bicyclo[4.1.0]heptan-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:

di-tert-butyl peroxide (110-05-4) + (C4H9)3SnO{C7H11} (62088-73-7) → bicyclo[4.1.0]heptan-2-one (5771-58-4) + 3-Methylcyclohexanone (591-24-2,625-96-7)

Guidance literature:

equimolar amts. of educts; at 130-140°C; ratio of products 76:24 (bicyclo:cyclo); the overall yield is higher than 50%;

DOI:10.1016/S0022-328X(00)84021-8

Reference yield:

bicyclo[4.1.0]heptane (286-08-8) → bicyclo[4.1.0]heptan-2-one (5771-58-4) + 3-chloromethylcyclohexene (19509-49-0) + endo-2-norcaranol (7432-49-7,6376-96-1,31022-87-4,38263-37-5,38263-38-6,136616-41-6) + exo-Bicyclo<4.1.0>heptan-2-ol (31022-87-4)

Guidance literature:

With iodosylbenzene; chloroaqua(tetraphenylporphinato)manganese(III); In dichloromethane; Yield given. Further byproducts given;

DOI:10.1021/ja00540a050

Reference yield:

bicyclo[4.1.0]heptane (286-08-8) → bicyclo[4.1.0]heptan-2-one (5771-58-4) + 3-hydroxymethylcyclohexene (103668-33-3,3309-97-5) + (3Z)-cyclohept-3-en-1-ol (6925-17-3) + bicyclo[4.1.0]heptan-3-one (60582-64-1) + endo-2-norcaranol (7432-49-7,6376-96-1,31022-87-4,38263-37-5,38263-38-6,136616-41-6) + bicyclo<4.1.0>heptanol-3 exo + bicyclo<4.1.0>heptanol-3 endo

Guidance literature:

With DL-dithiothreitol; Pseudomonas putida GPo₁ alkane hydroxylase; β-nicotinamide adenine dinucleotide?reduced; In glycerol; pH=7.4; Kinetics; aq. phosphate buffer;

DOI:10.1002/anie.200801184

upstream raw materials:

bicyclo[4.1.0]heptane

di-tert-butyl peroxide

(C₄H₉)3SnO{C₇H₁₁}

Downstream raw materials:

1-acetoxy-3-(acetoxymethyl)cyclohexene

1,4-diacetoxycycloheptene

C₁₆H₂₂O₄

C₂₁H₂₀O₂