Norcarane

Base Information

• Chemical Name: Norcarane
• CAS No.: 286-08-8
• Molecular Formula: C7H12
• Molecular Weight: 96.1723
• Hs Code.: 2902199090
• NSC Number: 143399
• DSSTox Substance ID: DTXSID10870493
• Nikkaji Number: J10.624K
• Wikipedia: Norcarane
• Wikidata: Q680932
• Mol file: 286-08-8.mol

Synonyms:norcarane

Chemical Property of Norcarane

Chemical Property:

• Vapor Pressure: 21.6mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: nD25 1.4546
• Boiling Point: 116.5°C at 760 mmHg
• PSA: 0.00000
• Density: 0.914
• LogP: 2.19650
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 96.093900383
• Heavy Atom Count: 7
• Complexity: 66.1

Purity/Quality:

99%, ^*data from raw suppliers

NORCARANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Solvents -> Aliphatics, Saturated (
• Canonical SMILES: C1CCC2CC2C1

Technology Process of Norcarane

There total 17 articles about Norcarane 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: 70.0%

C13H15NO2S → 3-methyl-1-cyclohexene (591-48-0) + bicyclo[4.1.0]heptane (286-08-8) + Cycloheptene (628-92-2,45509-99-7)

Guidance literature:

With thiophenol; Irradiation;

DOI:10.1002/anie.200603282

Reference yield: 64.2%

cyclohexene (110-83-8) + 1,1-dibromomethane (74-95-3) → methyl bromide (74-83-9) + ethene (74-85-1) + bicyclo[4.1.0]heptane (286-08-8)

Guidance literature:

With zinc; In tetrahydrofuran; at 40 ℃; for 48h; Product distribution; other olefins; also in the presence of Zn-Cu and Zn-CuCl; other solvents; var. temp.;

DOI:10.1016/0022-328X(84)80305-8

Reference yield: 44.0%

7,7-dichloro-bicyclo[4.1.0]heptane (823-69-8) + 9,10-dihydro-9,10-anthracendiyl-tris(THF)magnesium (86901-19-1) → 7-chloro-norcarane (1588-50-7) + bicyclo[4.1.0]heptane (286-08-8) + bicyclo[3.1.1]heptane (286-34-0) + tricyclo<3,2,0,02,7>heptane (279-18-5) + 9-Bicyclo[4.1.0]hept-7-yl-9,10-dihydro-anthracene (110079-21-5) + 9,10-Bis-bicyclo[4.1.0]hept-7-yl-9,10-dihydro-anthracene (110079-22-6)

Guidance literature:

In tetrahydrofuran; at -20 ℃; Product distribution; Mechanism; influence of halogen and reaction temperature;

upstream raw materials:

methylene

cyclohexene

tetrahydrofuran

7-exo-bromo-7-endo-chlorobicyclo<4.1.0>heptane

Downstream raw materials:

trans-2-iodomethylcyclohexyl acetate

2,2-dimethyl-1-(2-methyl-cyclohex-2-enyl)-propan-1-one

2-((1R,2S)-2-Methoxy-cyclohexylmethyl)-succinic acid diethyl ester

4-((1R,2S)-2-Methoxy-cyclohexyl)-3-methyl-butyronitrile

Refernces

• 1、 Fabisch, Bodo,Mitchell, Terence N.. "AN INEXPENSIVE INFLUENCE MODIFICATION OF THE SIMMONS-SMITH REACTION: THE FORMATION OF BROMOMETHYLZINC BROMIDE AS STUDIED BY NMR SPECTROSCOPY". . p. 219 - 222. Retrieved 1984.
• 2、 Kupfer, Rene,Brinker, Udo H.. "Carbenes in Constrained Systems, 3. Solid-State Photolysis of Cycloheptane- and Cyclooctanespirodiazirine within Cyclodextrins and Zeolites". . p. 1721 - 1726. Retrieved 2007/10/03.
• 3、 Bogdanovic, Borislav,Schlichte, Klaus,Westeppe, Uwe. "Dehalogenation of Geminal Dihalocyclopropanes, α,α-Dichlorocyclobutanones, and Haloketones by Means of Magnesium Anthracene*3THF". . p. 27 - 32. Retrieved 2007/10/02.