cis-1,2-Diphenyl-1-methylcyclopropane

Base Information

• Chemical Name: cis-1,2-Diphenyl-1-methylcyclopropane
• CAS No.: 14161-72-9
• Molecular Formula: C16H16
• Molecular Weight: 208.303
• DSSTox Substance ID: DTXSID40931142
• Nikkaji Number: J1.668.383C
• Mol file: 14161-72-9.mol

Synonyms:cis-1,2-Diphenyl-1-methylcyclopropane;trans-1,2-Diphenyl-1-methylcyclopropane;1,1'-(1-methylcyclopropane-1,2-diyl)dibenzene;14161-72-9;1-Methyl-1,2-diphenylcyclopropane;DTXSID40931142;STK328102;14161-73-0

Chemical Property of cis-1,2-Diphenyl-1-methylcyclopropane

Chemical Property:

• Boiling Point: 294.8°Cat760mmHg
• Flash Point: 134°C
• PSA: 0.00000
• Density: 1.041g/cm³
• LogP: 4.13180
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 208.125200510
• Heavy Atom Count: 16
• Complexity: 232

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC1C2=CC=CC=C2)C3=CC=CC=C3

Technology Process of cis-1,2-Diphenyl-1-methylcyclopropane

There total 38 articles about cis-1,2-Diphenyl-1-methylcyclopropane 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: 90.0%

(2RS,4SR)-2,4-diphenyl-4-tributyltinbutan-2-ol → ((1RS,2RS)-1-methylcyclopropane-1,2-diyl)dibenzene (14161-72-9)

Guidance literature:

With boron trifluoride diacetate; In dichloromethane; at 0 ℃;

DOI:10.1016/0022-328X(85)87366-6

Reference yield: 75.0%

iodobenzene (591-50-4) + 4,4,5,5-tetramethyl-2-[(1R,2R)-2-methyl-2-phenylcyclopropyl]-1,3,2-dioxaborolane → ((1R,2S)-1-methylcyclopropane-1,2-diyl)dibenzene (14161-72-9,14161-73-0,68579-43-1,98746-57-7,98746-58-8)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium tert-butylate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In 1,2-dimethoxyethane; tert-butyl alcohol; at 60 ℃; for 16h; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja510419z

Reference yield: 69.0%

C16H14Cl2 → ((1RS,2RS)-1-methylcyclopropane-1,2-diyl)dibenzene (14161-72-9)

Guidance literature:

With sodium; tert-butyl alcohol; In tetrahydrofuran; for 12h; Heating;

DOI:10.1002/jps.2600711012

upstream raw materials:

phenyldiazomethane

isopropenylbenzene

3-methyl-3-phenylcyclopropene

diphenylzinc

Downstream raw materials:

3,5-diphenyl-5-methyl-4,5-dihydroisoxazole

Refernces

• 1、 Allouche, Emmanuelle M. D.,Al-Saleh, Afnan,Charette, André B.. "Iron-catalyzed synthesis of cyclopropanes by in situ generation and decomposition of electronically diversified diazo compounds". . p. 13256 - 13259. Retrieved 2018/12/11.
• 2、 Müller, Daniel S.,Marek, Ilan. "Asymmetric Copper-Catalyzed Carbozincation of Cyclopropenes en Route to the Formation of Diastereo- and Enantiomerically Enriched Polysubstituted Cyclopropanes". supporting information. p. 15414 - 15417. Retrieved 2015/12/26.