(2S,8S)-8-methyl-2-decanol propanoate | 95840-36-1

• 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: (2S,8S)-8-methyl-2-decanol propanoate
• 英文别名: (2S,8S)-(+)-8-Methyldec-2-yl Propanoate；(2S,8S)-8-methyldecan-2-yl propionate；(2S,8S)-8-methyl-dec-2-ol propionate；[(2S,8S)-8-methyldecan-2-yl] propanoate
• CAS: 95840-36-1
• 化学式: C₁₄H₂₈O₂
• 分子量: 228.375
• InChiKey: DHRLLFVOVDPRNS-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,8S)-8-methyl-2-decanol propanoate 在 氢氧化钾 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 苯 为溶剂， 反应 48.0h， 生成 (2R,8S)-(+)-8-Methyldec-2-yl Propanoate
  参考文献：
  名称：

  Thermostable enzymes in organic synthesis. 7. Total synthesis of the western corn rootworm sex pheromone 8-methyldec-2-yl propanoate using a TBADH-generated C2-bifunctional chiron

  摘要：

  Enantiomerically pure alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalyzed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis. This advantage has been demonstrated by a total synthesis of all four isomers of 8-methyldec-2-yl propanoate, the sex pheromone emitted by the female western corn rootworm, Diabrotica virgifera virgifera LeConte. These four isomers were obtained in a very short procedure (either three or five steps) with an enantiomeric purity that exceeds 99% using a single chiral building block, (2S,8S)-(+)-2,8-dihydroxynonane. The latter diol, characterized by a synthetically useful C2 symmetry, was obtained by TBADH-catalyzed reduction of nonane-2,8-dione.

  DOI：

  10.1021/jo00039a023
• 作为产物：
  描述：

  (2S,8S)-(+)-dihydroxynonane 在 吡啶 、 copper(l) iodide 、 正丁基锂 作用下， 反应 24.83h， 生成 (2S,8S)-8-methyl-2-decanol propanoate
  参考文献：
  名称：

  Thermostable enzymes in organic synthesis. 7. Total synthesis of the western corn rootworm sex pheromone 8-methyldec-2-yl propanoate using a TBADH-generated C2-bifunctional chiron

  摘要：

  Enantiomerically pure alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalyzed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis. This advantage has been demonstrated by a total synthesis of all four isomers of 8-methyldec-2-yl propanoate, the sex pheromone emitted by the female western corn rootworm, Diabrotica virgifera virgifera LeConte. These four isomers were obtained in a very short procedure (either three or five steps) with an enantiomeric purity that exceeds 99% using a single chiral building block, (2S,8S)-(+)-2,8-dihydroxynonane. The latter diol, characterized by a synthetically useful C2 symmetry, was obtained by TBADH-catalyzed reduction of nonane-2,8-dione.

  DOI：

  10.1021/jo00039a023

文献信息

• Synthesis of two stereoisomers of the propanoate ester of 8-methyl-2-decanol using remote asymmetric induction
  作者：J.Tércio B. Ferrelra、Fabio Simonelli

  DOI：10.1016/s0040-4020(01)96003-x

  日期：1990.1

  A stereoselective synthesis of two isomers (2S,8R) and (2S,8S) of 8-methyl-2-decanol opanoate (the pheromone emitted by females of several Diabrotica species) has been accomplished using mote stereochemical relationships between carbons 3 and 9 of the 3,9-dimethyl decanolides 14 and 16.

  利用碳的3和9碳原子之间的分子立体化学关系，完成了8-甲基-2-癸醇戊酸酯的两个异构体（2S，8R）和（2S，8S）的立体选择性合成（几种Diabrotica物种的雌性释放的信息素）。 3，9-二甲基癸醇化物14和16。
• 美国西方玉米根虫性信息素的合成方法及其 应用
  申请人：西北农林科技大学

  公开号：CN108191655B

  公开（公告）日：2021-05-28

  本发明农药化学技术领域，公开一种美国西方玉米根虫性信息素的合成方法，其是将手性砜类化合物(S)‑2‑甲基丁基噻唑砜、(R)‑2‑甲基丁基噻唑砜分别与手性醛类化合物(S)‑6‑醛基己‑2‑醇丙酸酯、(R)‑6‑醛基己‑2‑醇丙酸酯进行Julia‑Kocienski偶联反应，所述偶联反应产物的双键经氢化还原，即得所述美国西方玉米根虫性信息素。此外，本发明所述美国西方玉米根虫性信息素应用于玉米根虫的防治。本发明简化了美国西方玉米根虫性信息素的合成路线，反应副产物较少，反应收率得到较大提高。
• Asymmetric Total Synthesis of Four Stereoisomers of the Sex Pheromone of the Western Corn Rootworm
  作者：Zhi-Feng Sun、Tao Zhang、Jinyang Liu、Zhen-Ting Du、Huaiji Zheng

  DOI：10.3390/molecules23030667

  日期：——

  A convergent synthesis of four stereoisomers of the sex pheromone of the western corn rootworm (8-methyldecan-2-yl propionate, 1) from commercially available chiral starting materials is reported. The key step was Julia–Kocienski olefination between chiral BT-sulfone and chiral aldehyde. This synthetic route provided the four stereoisomers of 1 in 24–29% total yield via a six-step sequence. The simple

  报道了从市售手性起始材料合成西部玉米根虫性信息素的四种立体异构体（8-methyldecan-2-yl propionate, 1）。关键步骤是手性 BT-砜和手性醛之间的 Julia-Kocienski 烯化。该合成路线通过六步序列以 24-29% 的总产率提供了 1 的四种立体异构体。简单的放大策略为实现性信息素的不对称合成提供了一种新方法。
• Thermostable enzymes in organic synthesis. 7. Total synthesis of the western corn rootworm sex pheromone 8-methyldec-2-yl propanoate using a TBADH-generated C2-bifunctional chiron
  作者：Ehud Keinan、Subhash C. Sinha、Anjana Sinha-Bagchi

  DOI：10.1021/jo00039a023

  日期：1992.6

  Enantiomerically pure alcohols produced by Thermoanaerobium brockii alcohol dehydrogenase (TBADH)-catalyzed asymmetric reduction of polyfunctional ketones are useful building blocks for natural products synthesis. This advantage has been demonstrated by a total synthesis of all four isomers of 8-methyldec-2-yl propanoate, the sex pheromone emitted by the female western corn rootworm, Diabrotica virgifera virgifera LeConte. These four isomers were obtained in a very short procedure (either three or five steps) with an enantiomeric purity that exceeds 99% using a single chiral building block, (2S,8S)-(+)-2,8-dihydroxynonane. The latter diol, characterized by a synthetically useful C2 symmetry, was obtained by TBADH-catalyzed reduction of nonane-2,8-dione.