(1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane

Base Information

• Chemical Name: (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane
• CAS No.: 139492-31-2
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.205
• Mol file: 139492-31-2.mol

Synonyms:(1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane

Chemical Property of (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane

There total 45 articles about (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane 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%

diiodomethane (75-11-6) + (Z)-cinnamyl alcohol (4510-34-3) → (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane (139492-31-2)

Guidance literature:

With (R,R)-1-butyl-3,4-bis(dimethylaminocarbonyl)-1,3-dioxaboralane; diethylzinc;

DOI:10.1021/jo961235p

Reference yield: 50.0%

phenyldiazomethane (908094-04-2) + allyl alcohol (107-18-6) → trans-(3-phenylcyclopropyl)methanol (79981-48-9) + rac-((1S,2R)-2-phenylcyclopropyl)methanol (936-98-1,1007-09-6,10488-04-7,29667-46-7,61826-40-2,79981-48-9,110659-58-0,139492-31-2)

Guidance literature:

allyl alcohol; With sodium hydride; zinc(II) iodide; In dichloromethane; mineral oil; at 0 ℃; for 0.0833333h; Inert atmosphere;

phenyldiazomethane; In dichloromethane; mineral oil; at -20 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ja9074776

Reference yield:

diiodomethane (75-11-6) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (1R,2S)-cis-1-(Hydroxymethyl)-2-phenylcyclopropane (139492-31-2) + (1S,2R)-2-phenylcyclopropylmethanol (29667-46-7)

Guidance literature:

With (R,S)-1,2-cyclohexanebis(methanesulfonamide); iodine; diethylzinc; In dichloromethane; at 0 ℃; for 45h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo9702397

upstream raw materials:

(1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one

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

diiodomethane

(Z)-cinnamyl alcohol

Downstream raw materials:

rac-(1S,2R)-2-phenylcyclopropanecarbaldehyde

(1R,2S)-1-formyl-2-phenylcyclopropane

(1S,2R)-1-formyl-2-phenylcyclopropane

(1S,2R)-2-phenylcyclopropylmethanol

Refernces

• 1、 Charette, André B.,Navuluri, Chandrasekhar,Siddiqui, Saher H.. "Enantioselective Synthesis of cis- A nd trans-Borocyclopropylmethanol: Simple Building Blocks to Access Heterocycle-Substituted Cyclopropylmethanols". . p. 3834 - 3846. Retrieved 2019.
• 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.