(S)-(-)-2-phenyl-4-penten-2-ol

Base Information

• Chemical Name: (S)-(-)-2-phenyl-4-penten-2-ol
• CAS No.: 100350-03-6
• Molecular Formula: C₁₁H₁₄O
• Molecular Weight: 162.232
• Mol file: 100350-03-6.mol

Synonyms:

Chemical Property of (S)-(-)-2-phenyl-4-penten-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(-)-2-phenyl-4-penten-2-ol

There total 55 articles about (S)-(-)-2-phenyl-4-penten-2-ol 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: 99.0%

tetraallyl tin (7393-43-3) + acetophenone (98-86-2) → (R)-2-phenyl-pent-4-en-2-ol (4743-74-2,100350-03-6,110577-97-4)

Guidance literature:

tetraallyl tin; With titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; In dichloromethane; isopropyl alcohol; at 20 ℃; for 24h; Inert atmosphere;

acetophenone; In dichloromethane; isopropyl alcohol; at 20 ℃; for 24h; optical yield given as %ee; enantiospecific reaction; Inert atmosphere;

DOI:10.1016/j.tet.2010.03.048

Reference yield: 89.0%

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (72824-04-5) + acetophenone (98-86-2) → (S)-(-)-2-phenyl-4-penten-2-ol (4743-74-2,110577-97-4,100350-03-6)

Guidance literature:

With methanol; (S)-2-((2-hydroxy-3-(triphenylsilyl)benzyl)amino)-3-methyl-1-(pyrrolidin-1-yl)butan-1-one; sodium t-butanolate; In tetrahydrofuran; toluene; at -30 ℃; for 24h;

Reference yield: 89.0%

diisopropyl allylboronate (51851-79-7) + acetophenone (98-86-2) → (S)-(-)-2-phenyl-4-penten-2-ol (4743-74-2,110577-97-4,100350-03-6)

Guidance literature:

acetophenone; With C₂₀H₂₂Br₂O₂Si; In toluene; at 0 ℃; for 0.0833333h; Inert atmosphere; Sealed tube;

diisopropyl allylboronate; In toluene; at 0 ℃; for 12h; Reagent/catalyst; Inert atmosphere; Sealed tube;

upstream raw materials:

tetraallyl tin

acetophenone

allyltrimethoxysilane

allyltributylstanane

Downstream raw materials:

(R)-tert-butyldimethyl(2-phenylpent-4-en-2-yloxy)silane

(2S,4R)-4-phenylpentane-1,2,4-triol

(2R,4R)-4-phenylpentane-1,2,4-triol

(R)-1-methoxy-4-((2-phenylpent-4-en-2-yloxy)methyl)-benzene

Refernces

• 1、 Johnson, A. George,Loertscher, Brad M.,Moeck, Adam R.,Matthews, Sam S.,Ess, Daniel H.,Castle, Steven L.. "Experimental and theoretical investigation of the scope of enantioselective ketone allylations employing Nakamura's allylzinc-bisoxazoline reagent". . p. 2706 - 2710. Retrieved 2011.
• 2、 Haddad, Terra D.,Hirayama, Lacie C.,Taynton, Philip,Singaram, Bakthan. "Asymmetric indium-mediated Barbier-type allylation reactions with ketones to form homoallylic alcohol products". . p. 508 - 511. Retrieved 2008.
• 3、 Casolari, Sonia,D'Addario, Daniela,Tagliavini, Emilio. "BINOL-Ti-catalyzed synthesis of tertiary homoallylic alcohols: The first catalytic asymmetric allylation of ketones". . p. 1061 - 1063. Retrieved 1999.
• 4、 Lee, Kyunga,Silverio, Daniel L.,Torker, Sebastian,Robbins, Daniel W.,Haeffner, Fredrik,Van Der Mei, Farid W.,Hoveyda, Amir H.. "Catalytic enantioselective addition of organoboron reagents to fluoroketones controlled by electrostatic interactions". . p. 768 - 777. Retrieved 2016.
• 5、 Hanawa, Hideo,Kii, Satoshi,Maruoka, Keiji. "New Chiral Bis-Titanium(IV) Catalyst with Dibenzofuran Spacer for Catalytic Asymmetric Allylation of Aldehydes and Aryl Ketones". . p. 57 - 60. Retrieved 2001.
• 6、 Rasson, Corentin,Riant, Olivier. "Copper(I) Diphosphine Bifluoride Complexes as Efficient Preactivated Catalysts for Nucleophilic Addition on Unsaturated Functional Groups". . p. 835 - 840. Retrieved 2020.
• 7、 Lou, Sha,Moquist, Philip N.,Schaus, Scott E.. "Asymmetric allylboration of ketones catalyzed by chiral diols". . p. 12660 - 12661. Retrieved 2006.
• 8、 Liu, Jin-Yu,Yang, Xie-Chao,Liu, Zhen,Luo, Yong-Chun,Lu, Hong,Gu, Yu-Cheng,Fang, Ran,Xu, Peng-Fei. "An Atropo-enantioselective Synthesis of Benzo-Linked Axially Chiral Indoles via Hydrogen-Bond Catalysis". . p. 5219 - 5224. Retrieved 2019.