Benzyl 2-cyclohexen-1-ylcarbamate

Base Information

• Chemical Name: Benzyl 2-cyclohexen-1-ylcarbamate
• CAS No.: 91230-17-0
• Molecular Formula: C14H17NO2
• Molecular Weight: 231.294
• DSSTox Substance ID: DTXSID80437552
• Nikkaji Number: J1.992.014C
• Mol file: 91230-17-0.mol

Synonyms:91230-17-0;Benzyl 2-cyclohexen-1-ylcarbamate;Carbamic acid, 2-cyclohexen-1-yl-, phenylmethyl ester;CTK3I1221;SCHEMBL17764632;DTXSID80437552;BFBDOBJZUPOVMQ-UHFFFAOYSA-N;2-Cyclohexenylcarbamic acid benzyl ester;FT-0723881;BENZYL N-(CYCLOHEX-2-EN-1-YL)CARBAMATE

Chemical Property of Benzyl 2-cyclohexen-1-ylcarbamate

Chemical Property:

• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 231.125928785
• Heavy Atom Count: 17
• Complexity: 269

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC=CC(C1)NC(=O)OCC2=CC=CC=C2

Technology Process of Benzyl 2-cyclohexen-1-ylcarbamate

There total 8 articles about Benzyl 2-cyclohexen-1-ylcarbamate 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: 96.0%

O-benzyl carbamate (621-84-1) + cyclohexa-1,3-diene (1165952-91-9) → benzyl (RS)-cyclohex-2-en-1-ylcarbamate (91230-17-0)

Guidance literature:

With silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 50 ℃; for 23h; Inert atmosphere; Darkness;

DOI:10.1002/adsc.201100478

Reference yield: 91.0%

O-benzyl carbamate (621-84-1) + Cyclohex-2-enol (822-67-3) → benzyl (RS)-cyclohex-2-en-1-ylcarbamate (91230-17-0)

Guidance literature:

With calcium(II) bis(trifluoromethanesulfonyl)imide; tert-butylammonium hexafluorophosphate(V); In dichloromethane; at 20 ℃; for 3.5h;

DOI:10.1002/adsc.201000768

Reference yield: 85.0%

isocyanate de chlorosulfonyle (1189-71-5) + [(cyclohex-2-en-1-yloxy)methyl]benzene (32700-48-4) → benzyl (RS)-cyclohex-2-en-1-ylcarbamate (91230-17-0)

Guidance literature:

[(cyclohex-2-en-1-yloxy)methyl]benzene; With sodium carbonate; In dichloromethane; at 0 ℃; for 0.333333h; Inert atmosphere;

isocyanate de chlorosulfonyle; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

With sodium sulfite; In water; ethyl acetate; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.02.036

upstream raw materials:

O-benzyl carbamate

3-phenylselenocyclohexene

sodium [(benzyloxy)carbonyl]chloroamide

2-cyclohexenylamine hydrochloride

Downstream raw materials:

O-benzyl carbamate

N-cyclohex-2-enyl-4-methyl-benzenesulfonamide

Refernces

• 1、 Das, Braja Gopal,Nallagonda, Rajender,Ghorai, Prasanta. "Direct substitution of hydroxy group of π-activated alcohols with electron-deficient amines using Re2O7 catalyst". experimental part. p. 5577 - 5583. Retrieved 2012/07/31.
• 2、 Haubenreisser, Stefan,Niggemann, Meike. "Calcium-catalyzed direct amination of π-activated alcohols". supporting information; experimental part. p. 469 - 474. Retrieved 2011/04/16.