(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S)-7-hydroxy-1-methyl-octyl ester | 141667-23-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S)-7-hydroxy-1-methyl-octyl ester
• CAS: 141667-23-4
• 化学式: C₁₉H₂₇F₃O₄
• 分子量: 376.416
• InChiKey: FRRKGUDWLXRYAT-RLFYNMQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  26.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S)-7-hydroxy-1-methyl-octyl ester 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S)-1-methyl-7-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octyl ester
  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：

  甲氧基-三氟甲基苯 、 (2S,8S)-(+)-dihydroxynonane 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S)-7-hydroxy-1-methyl-octyl ester
  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