diethyl 2-benzoyl-3-phenyl-cyclopropane-1,1-dicarboxylate

Base Information

• Chemical Name: diethyl 2-benzoyl-3-phenyl-cyclopropane-1,1-dicarboxylate
• CAS No.: 6327-84-0
• Molecular Formula: C₂₂H₂₂O₅
• Molecular Weight: 366.414
• Mol file: 6327-84-0.mol

Synonyms:1,1-Cyclopropanedicarboxylicacid, 2-benzoyl-3-phenyl-, diethyl ester (9CI); NSC 17511

Chemical Property of diethyl 2-benzoyl-3-phenyl-cyclopropane-1,1-dicarboxylate

Chemical Property:

• Vapor Pressure: 1.2E-11mmHg at 25°C
• Boiling Point: 538.1°C at 760 mmHg
• Flash Point: 279.2°C
• PSA: 69.67000
• Density: 1.417g/cm³
• LogP: 3.39550

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of diethyl 2-benzoyl-3-phenyl-cyclopropane-1,1-dicarboxylate

There total 12 articles about diethyl 2-benzoyl-3-phenyl-cyclopropane-1,1-dicarboxylate 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: 94.0%

diethyl 2-(3-oxo-1,3-diphenylpropyl)malonate (77670-30-5,7472-83-5) → diethyl trans-2-benzoyl-3-phenylcyclopropane-1,1-dicarboxylate (6327-84-0,24959-21-5,136289-55-9)

Guidance literature:

With tert.-butylhydroperoxide; N-iodo-succinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,4-dioxane; water; at 50 ℃; for 2h; Catalytic behavior;

DOI:10.1039/c6cc06624k

Reference yield: 92.0%

benzalacetophenone (94-41-7) + diethyl malonate (105-53-3) → diethyl trans-2-benzoyl-3-phenylcyclopropane-1,1-dicarboxylate (6327-84-0,24959-21-5,136289-55-9)

Guidance literature:

With iodine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; at 20 ℃;

DOI:10.1002/adsc.201300861

Reference yield: 88.0%

2-bromo-1,3-diphenyl-2-propen-1-one (6935-75-7) + diethyl malonate (105-53-3) → diethyl trans-2-benzoyl-3-phenylcyclopropane-1,1-dicarboxylate (6327-84-0,24959-21-5,136289-55-9)

Guidance literature:

With potassium carbonate; In dimethyl sulfoxide; at 80 ℃; for 13h; Time; diastereoselective reaction;

DOI:10.1016/j.tet.2013.02.011

upstream raw materials:

diethyl dibromomalonate

benzalacetophenone

diethyl benzalmalonate

(benzoylmethylene)dimethylsulfurane

Downstream raw materials:

7-phenyl-dibenzo[c,h]acridine

Refernces

• 1、 Liu, Jiaming,Wang, Lizhong,Qing, Xushun,Zhang, Feixiang,Wang, Ting,Wang, Cunde. "Synergistic NaBH4Reduction/Cyclization of 2-Aroylcyclopropane-1-carboxylates: Synthesis of 3-Oxabicyclo[3.1.0]hexane Derivatives". supporting information. p. 1012 - 1018. Retrieved 2017/02/15.
• 2、 Sathishkannan, Gopal,Srinivasan, Kannupal. "Lewis acid-mediated transformations of trans-2-Aroyl-3-aryl-cyclopropane-1, 1-dicarboxylates into 2-pyrones and 1-indanones". supporting information. p. 729 - 735. Retrieved 2014/04/03.