(S)-(+)-2-ethylheptanol | 500304-23-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-(+)-2-ethylheptanol
• 英文别名: (2S)-ethyl-1-heptanol；2-Ethylheptanol, (S)-；(2S)-2-ethylheptan-1-ol
• CAS: 500304-23-4
• 化学式: C₉H₂₀O
• 分子量: 144.257
• InChiKey: QNJAZNNWHWYOEO-VIFPVBQESA-N

物化性质

• 沸点：
  196.6±8.0 °C(Predicted)
• 密度：
  0.824±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  6
• 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

• 作为反应物：
  描述：

  3,4,5-三甲氧基苯甲酰氯 、 (S)-(+)-2-ethylheptanol 在 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以81 %的产率得到(S)-2-ethylheptyl 3,4,5-trimethoxybenzoate
  参考文献：
  名称：

  铜催化区域发散的内部烯丙基烷基化

  摘要：

  我们报告了使用官能化烷基和芳基格氏试剂铜催化内烯丙基碳酸酯烷基化的研究。该反应对S N 2 或S N 2' 产物表现出良好的区域选择性，使得能够制备具有E-烯烃选择性的产物。密度泛函理论（DFT）计算揭示了基于同铜酸盐和异铜酸盐的不同行为的区域选择性的起源。

  DOI：

  10.1002/anie.202304848
• 作为产物：
  描述：

  (S)-4-苄基-3-庚酰基噁唑啉-2-酮 在 lithium aluminium tetrahydride 、 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 (S)-(+)-2-ethylheptanol
  参考文献：
  名称：

  On the absolute stereochemistry of (−)-4-alkylnonan-2-ones

  摘要：

  The alcohols (S)-(C5H11CH)-C-n(R)CH2OH (R = Me, Et) have been prepared by Evans' alkylation chemistry (>98% e.e.). For R = Me [alpha](D) = -15.5 (c 0.31, MeOH); for R = Et [alpha](D) = +6.8 (c 0.31, MeOH). Equivalent alcohols are obtained by Baeyer-Villiger oxidative cleavage of (S)-(-)-(C5H11CH)-C-n(R)CH2COMe (R = Me, 85% e.e.; R = Et, 62% e.e.) derived from catalytic asymmetric conjugate addition. Thus, AlMe3 or ZnEt2 addition to the Si face of the enone generates a (-) antipode with a 4S stereocentre. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00574-8

文献信息

• 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.
• FOAM CONTROL
  申请人：Dow Global Technologies, LLC

  公开号：EP3764821A1

  公开（公告）日：2021-01-20
• [EN] FOAM CONTROL<br/>[FR] RÉGULATION DE MOUSSE
  申请人：DOW GLOBAL TECHNOLOGIES LLC

  公开号：WO2019177726A1

  公开（公告）日：2019-09-19

  A method for controlling foam comprising providing a food composition comprising a foam control agent and a foodstuff, the foam control agent; and processing the food composition. A food composition comprising a foodstuff and a foam control agent.
• On the absolute stereochemistry of (−)-4-alkylnonan-2-ones
  作者：Victor Garcia-Ruiz、Simon Woodward

  DOI：10.1016/s0957-4166(02)00574-8

  日期：2002.10

  The alcohols (S)-(C5H11CH)-C-n(R)CH2OH (R = Me, Et) have been prepared by Evans' alkylation chemistry (>98% e.e.). For R = Me [alpha](D) = -15.5 (c 0.31, MeOH); for R = Et [alpha](D) = +6.8 (c 0.31, MeOH). Equivalent alcohols are obtained by Baeyer-Villiger oxidative cleavage of (S)-(-)-(C5H11CH)-C-n(R)CH2COMe (R = Me, 85% e.e.; R = Et, 62% e.e.) derived from catalytic asymmetric conjugate addition. Thus, AlMe3 or ZnEt2 addition to the Si face of the enone generates a (-) antipode with a 4S stereocentre. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Copper‐Catalyzed Regiodivergent Internal Allylic Alkylations
  作者：Madhu Sudan Manna、Seok Yeol Yoo、Mohammed Sharique、Hyoju Choi、Bimal Pudasaini、Mu‐Hyun Baik、Uttam K. Tambar

  DOI：10.1002/anie.202304848

  日期：2023.8.28

  We report on a study of copper-catalyzed alkylation of internal allylic carbonates using functionalized alkyl and aryl Grignard reagents. The reactions exhibit good regioselectivity for either SN2 or SN2′ products, enabling the preparation of products with E-alkene selectivity. Density functional theory (DFT) calculations reveal the origins of the regioselectivity based on the different behaviors of

  我们报告了使用官能化烷基和芳基格氏试剂铜催化内烯丙基碳酸酯烷基化的研究。该反应对S N 2 或S N 2' 产物表现出良好的区域选择性，使得能够制备具有E-烯烃选择性的产物。密度泛函理论（DFT）计算揭示了基于同铜酸盐和异铜酸盐的不同行为的区域选择性的起源。