(R)-1-phenyl-3-pentanol

Base Information

• Chemical Name: (R)-1-phenyl-3-pentanol
• CAS No.: 105836-17-7
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.247
• Mol file: 105836-17-7.mol

Synonyms:(R)-1-phenyl-3-pentanol

Chemical Property of (R)-1-phenyl-3-pentanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-phenyl-3-pentanol

There total 36 articles about (R)-1-phenyl-3-pentanol 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: 91.0%

3-phenyl-propionaldehyde (104-53-0) + diethylzinc (557-20-0) → (R)-1-phenyl-3-pentanol (105836-17-7)

Guidance literature:

3-phenyl-propionaldehyde; diethylzinc; With diphenyl-((R)-1-((S)-1-phenylethyl)aziridin-2-yl)-methanol; In hexane; toluene; at 0 - 25 ℃; for 48.5h; Inert atmosphere;

With ammonium chloride; In hexane; water; toluene; optical yield given as %ee; enantioselective reaction; Saturated solution;

DOI:10.1016/j.tetasy.2011.04.013

Reference yield: 89.0%

methylmagnesium bromide (75-16-1) + (S)-1,2-epoxy-4-phenylbutane (913258-22-7) → (R)-1-phenyl-3-pentanol (105836-17-7)

Guidance literature:

methylmagnesium bromide; With copper(l) iodide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.0833333h; Inert atmosphere;

(S)-1,2-epoxy-4-phenylbutane; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.1c02616

Reference yield: 69.0%

(S)-epichlorohydrin (67843-74-7,24969-06-0,13403-37-7) + methylmagnesium bromide (75-16-1) + phenylmagnesium bromide (1589-82-8) → (R)-1-phenyl-3-pentanol (105836-17-7)

Guidance literature:

phenylmagnesium bromide; With copper(l) iodide; In tetrahydrofuran; at -78 ℃; for 0.0833333h; Inert atmosphere;

(S)-epichlorohydrin; In tetrahydrofuran; at -78 - 20 ℃; for 3h; Inert atmosphere;

methylmagnesium bromide; Further stages;

DOI:10.1002/anie.201905173

upstream raw materials:

(1E,3R)-1-phenylpent-1-en-3-ol

3-phenyl-propionaldehyde

diethylzinc

1-phenyl-1-pentyn-3-ol

Downstream raw materials:

(R)-3-mesyloxy-1-phenylpentane

(S)-3-mesyloxy-1-phenylpentane

5-phenylpent-2-ene

(3R,4R,5S)-4-Acetylamino-5-azido-3-((R)-1-ethyl-3-phenyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

Refernces

• 1、 Harada, Toshiro,Nakatsugawa, Masashi. "Immobilization of a BINOLate-titanium catalyst by use of aggregation phenomenon". . p. 321 - 323. Retrieved 2006.
• 2、 Gennari, Cesare,Ceccarelli, Simona,Piarulli, Umberto,Montalbetti, Christian A. G. N.,Jackson, Richard F. W.. "Investigation of a New Family of Chiral Ligands for Enantioselective Catalysis via Parallel Synthesis and High-Throughput Screening". . p. 5312 - 5313. Retrieved 1998.
• 3、 Vidal-Ferran, Anton,Moyano, Albert,Pericas, Miquel A.,Riera, Antoni. "Computer assisted, mechanism directed design of a new ligand for the highly enantioselective catalytic addition of diethylzinc to aldehydes". . p. 8773 - 8776. Retrieved 1997.
• 4、 Harada, Toshiro,Kanda, Kousou,Hiraoka, Yuuki,Marutani, Yasuhisa,Nakatsugawa, Masashi. "Asymmetric alkylation of aldehydes catalyzed by novel dinuclear bis-BINOLate titanium(IV) complexes". . p. 3879 - 3883. Retrieved 2004.
• 5、 Huang, Jian,Ianni, James C.,Antoline, Jennifer E.,Hsung, Richard P.,Kozlowski, Marisa C.. "De novo chiral amino alcohols in catalyzing asymmetric additions to aryl aldehydes". . p. 1565 - 1568. Retrieved 2006.
• 6、 Wu, Nan,Bo, Rongcheng,Zhang, Rongli,Jiang, Xi,Wan, Yu,Xu, Zhou,Wu, Hui. "Enantioselective addition of diethylzinc to aldehydes by chiral oxazolidine-titanium complex". . p. 644 - 649. Retrieved 2012.
• 7、 Liu, Xingxing,Zhu, Qing,Chen, Du,Wang, Lu,Jin, Liqun,Liu, Chao. "Aminoazanium of DABCO: An Amination Reagent for Alkyl and Aryl Pinacol Boronates". supporting information. p. 2745 - 2749. Retrieved 2020/01/25.
• 8、 Zhang, Jinxia,Li, Shasha,Zheng, Xinxin,Li, Hongjie,Jiao, Peng. "Chiral zinc amidate catalyzed additions of diethylzinc to aldehydes". supporting information. p. 1913 - 1917. Retrieved 2019/06/24.