(2R)-ethyl-4-methyl-1-pentanol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-ethyl-4-methyl-1-pentanol
• 英文别名: (2R)-2-ethyl-4-methylpentan-1-ol
• 化学式: C₈H₁₈O
• 分子量: 130.23
• InChiKey: QCHSJPKDWOFACC-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-2-(碘甲基)丁烷-1-醇 、 异丙基氯化镁 在 1-苯基-1-丙炔 、 copper dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到(2R)-ethyl-4-methyl-1-pentanol
  参考文献：
  名称：

  通过锆催化烯烃的不对称碳铝化和钯或铜催化的交叉偶联广泛适用合成对映异构纯的含叔烷基的 1-烷醇

  摘要：

  已经开发了一种高对映选择性和广泛适用的方法，用于合成各种手性 2-烷基-1-烷醇，尤其是手性弱的那些。它由锆催化的烯烃不对称碳铝化（ZACA）、脂肪酶催化的乙酰化和钯或铜催化的交叉偶联组成。凭借与碘相关的高选择性因子 ( E )，通过烯丙醇的 ZACA 反应制备的 3-碘-2-烷基-1-烷醇 ( 1 ) 的( S )-或 ( R )-对映体可以易于纯化至 ≥ 99 % ee的水平通过脂肪酶催化的乙酰化。多种手性含叔烷基醇，包括那些原本难以制备的醇，现在可以通过 Pd-或 Cu 催化的(S)-1或(R)-2交叉偶联以高对映体纯度合成用于引入各种一级、二级和三级碳基团，同时保留所有碳骨架特征。这些手性含叔烷基的醇可以进一步转化为相应的酸，并完全保留立体化学。该方法的效用的合成已经在高度对映体选择性（≥99％被证明EE）和（高效合成- [R）-2-甲基-1-丁醇和（- [R ） -和（小号)-金黄酸。

  DOI：

  10.1002/asia.201300311

文献信息

• PROCESSES FOR THE SYNTHESIS OF CHIRAL 1-ALKANOLS
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：US20160332940A1

  公开（公告）日：2016-11-17

  The invention relates to highly enantioselective processes for the synthesis of chiral 1-alkanols via Zr-catalyzed asymmetric carboalumination of alkenes.

  这项发明涉及通过Zr催化的不对称烯烃碳硼烷化反应合成手性1-烷醇的高对映选择性过程。
• Processes for the synthesis of chiral 1-alkanols
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：US10000432B2

  公开（公告）日：2018-06-19

  The invention relates to highly enantioselective processes for the synthesis of chiral 1-alkanols via Zr-catalyzed asymmetric carboalumination of alkenes.

  本发明涉及通过 Zr 催化的烯烃不对称羧氨化合成手性 1-烷醇的高对映选择性工艺。
• Zirconium-Catalyzed Enantioselective Alkylalumination of Monosubstituted Alkenes Proceeding via Noncyclic Mechanism
  作者：Denis Y. Kondakov、Ei-ichi Negishi

  DOI：10.1021/ja953655m

  日期：1996.1.1
• Catalytic enantioselective ethylalumination of terminal alkenes: substrate effects and absolute configuration assignment
  作者：Lyudmila V. Parfenova、Pavel V. Kovyazin、Tatyana V. Tyumkina、Alyona V. Makrushina、Leonard M. Khalilov、Usein M. Dzhemilev

  DOI：10.1016/j.tetasy.2014.11.019

  日期：2015.2

  The chemo- and enantioselectivity of the reaction of alkenes with AlEt3 catalyzed by bis(1-neomenthyl-indenyl)zirconium dichloride has been studied. The reaction with linear alkenes in a chlorinated solvent (CH2Cl2) gives mainly carbometallation products in 70-80% yield and with enantiomeric purity of 47-70%ee with an (S)-configuration. In the case of vinylcycloalkanes and styrene, the reaction provides roughly equal amounts of carbometallation products and substituted alumolanes with enantioselectivities of 39-69%ee and 40-57%ee, respectively.(R)-MTPA and (R)-2-phenylselenopropionic acid [(R)-PSPA] were used as the derivatization reagents for enantiomeric excess estimation and the absolute configuration assignment of beta-chiral primary alcohols and 2-substituted 1,4-butanediols resulting from oxidation and hydrolysis of the organoaluminum products. It was shown that the specific rotation changes sign in the series of enantiomerically enriched 2-ethyl-1-alkanols when going from beta-ethyl-substituted octanol to nonanol. The conformational analysis of the MTPA and PSPA esters of 2-ethyl-1-alkanols was performed and a dependence of their conformational composition on the type of substituent at the beta-stereogenic center was established. Calculation of the Se-77 NMR chemical shifts of the possible conformers of the PSPA esters demonstrated that the conformation of the selenium moiety has the most pronounced effect on the delta(Se) value. The high efficiency of PSPA application for the enantiomeric purity estimation and the absolute configuration assignment of 2-ethyl-1-alkanols is shown. (C) 2014 Elsevier Ltd. All rights reserved.
• 1-(BENZO[D][1,3]DIOXOL-5-YL)-N-(PHENYL)CYCLOPROPANE-CARBOXAMIDE DERIVATIVES AND RELATED COMPOUNDS AS MODULATORS OF ATP-BINDING CASSETTE TRANSPORTERS FOR THE TREATMENT OF CYSTIC FIBROSIS
  申请人：VERTEX PHARMACEUTICALS INCORPORATED

  公开号：EP2016065B1

  公开（公告）日：2012-09-19