(2R,8S)-(+)-8-methyldecan-2-ol | 104435-71-4

• 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: (2R,8S)-(+)-8-methyldecan-2-ol
• 英文别名: (2R,8S)-8-methyldecan-2-ol
• CAS: 104435-71-4
• 化学式: C₁₁H₂₄O
• 分子量: 172.311
• InChiKey: QXDCUXPLCGLNNP-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  12
• 可旋转键数：
  7
• 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：

  丙酸 、 (2R,8S)-(+)-8-methyldecan-2-ol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 反应 24.0h， 以57%的产率得到(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 、 氢氧化钾 、 copper(l) iodide 、 正丁基锂 作用下， 以 甲醇 为溶剂， 反应 48.83h， 生成 (2R,8S)-(+)-8-methyldecan-2-ol
  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

• 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.