Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)

Base Information

• Chemical Name: Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)
• CAS No.: 82263-48-7
• Molecular Formula: C10H10O
• Molecular Weight: 146.189
• Mol file: 82263-48-7.mol

Synonyms:(1R,2R)-2-Phenyl-cyclopropanecarbaldehyde;2-phenylcyclopropanecarbaldehyde;2-phenyl-cyclopropanecarbaldehyde;(-)-(1R,2R)-2-Phenylcyclopropanecarbaldehyde;(1R,2R)-2-phenyl-cyclopropane-carboxaldehyde;trans-2-phenylcyclopropanecarbaldehyde;

Chemical Property of Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)

Chemical Property:

• PSA: 17.07000
• LogP: 1.98900

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI)

There total 74 articles about Cyclopropanecarboxaldehyde, 2-phenyl-, (1R,2R)- (9CI) 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: 95.0%

(1S,2S)-trans-1-(hydroxymethyl)-2-phenylcyclopropane (110659-58-0) → (1S,2S)-2-phenylcyclopropane-1-carbaldehyde (34271-30-2,34271-31-3,67074-44-6,79929-84-3,82263-48-7,82263-50-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 15h; Inert atmosphere;

DOI:10.1016/j.bmc.2017.02.004

Reference yield: 93.0%

(4R,5R)-2-((1R,2R)-2-Phenyl-cyclopropyl)-[1,3]dioxolane-4,5-dicarboxylic acid diisopropyl ester (99267-80-8) → trans-2- phenylcyclopropane-1-carbaldehyde (82263-48-7)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 60 ℃;

DOI:10.1039/c39940001783

Reference yield: 92.0%

(1R,2R)-1-hydroxymethyl-2-phenylcyclopropane (110659-58-0) → trans-2- phenylcyclopropane-1-carbaldehyde (82263-48-7)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2017.02.004

upstream raw materials:

(2S,4S,5R)-3,4-Dimethyl-5-phenyl-2-((1R,2R)-2-phenyl-cyclopropyl)-oxazolidine

(4R,5R)-2-((1R,2R)-2-Phenyl-cyclopropyl)-[1,3]dioxolane-4,5-dicarboxylic acid diethyl ester

(4R,5R)-2-((1R,2R)-2-Phenyl-cyclopropyl)-[1,3]dioxolane-4,5-dicarboxylic acid diisopropyl ester

[(1S,2S,4R,6R,7S)-10,10-Dimethyl-4-((1R,2R)-2-phenyl-cyclopropyl)-3,5-dioxa-tricyclo[5.2.1.0^2,6]dec-1-yl]-methanesulfonic acid phenyl ester

Downstream raw materials:

ethyl 3E-<(1S,2R)-2-phenyl-1-cyclopropyl>prop-1-enoate

ethyl 3E-<(1R,2S)-2-phenyl-1-cyclopropyl>prop-1-enoate

(1R,2R)-1-hydroxymethyl-2-phenylcyclopropane

C₁₇H₁₄OS

Refernces

• 1、 Beltran, Frédéric,Bergamaschi, Enrico,Teskey, Christopher J.. "Visible-Light Controlled Divergent Catalysis Using a Bench-Stable Cobalt(I) Hydride Complex". . p. 5180 - 5184. Retrieved 2020/04/22.
• 2、 Peese, Kevin M.,Allard, Christopher W.,Connolly, Timothy,Johnson, Barry L.,Li, Chen,Patel, Manoj,Sorensen, Margaret E.,Walker, Michael A.,Meanwell, Nicholas A.,McAuliffe, Brian,Minassian, Beatrice,Krystal, Mark,Parker, Dawn D.,Lewis, Hal A.,Kish, Kevin,Zhang, Ping,Nolte, Robert T.,Simmermacher, Jean,Jenkins, Susan,Cianci, Christopher,Naidu, B. Narasimhulu. "5,6,7,8-Tetrahydro-1,6-naphthyridine Derivatives as Potent HIV-1-Integrase-Allosteric-Site Inhibitors". . p. 1348 - 1361. Retrieved 2019/02/24.