[(2E,6E)-2,6-dimethyl-8-(oxan-2-yloxy)octa-2,6-dienyl] 2,2-dimethylpropanoate | 254742-48-8

• 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: [(2E,6E)-2,6-dimethyl-8-(oxan-2-yloxy)octa-2,6-dienyl] 2,2-dimethylpropanoate
• CAS: 254742-48-8
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: RWVTUNIQJXAPKN-VMHPKHSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(2E,6E)-2,6-dimethyl-8-(oxan-2-yloxy)octa-2,6-dienyl] 2,2-dimethylpropanoate 在 碘 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (11S)-10,11-dihydrogeranylgeraniol
  参考文献：
  名称：

  Synthesis of (1S,2R,12S)-2-hydroxy-11-dihydroneocembrene

  摘要：

  Aiming at the asymmetric total synthesis of trinervitane-type diterpenes, an efficient synthetic route to the title compound was explored starting from the THP ether of pivaloyloxy geraniol 11e. The coupling reaction with Grignard reagent 14 bearing the stereogenic carbon proceeded smoothly to give the THP ether of (11S)-10-dihydrogeranylgeraniol 10. Conversion to the corresponding acid chloride through the intermediate 9, followed by cyclization, afforded the dihydrocembrene derivative 8, from which the title compound 7 was prepared. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00376-6
• 作为产物：
  描述：

  8-hydroxygeranyl acetate 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 [(2E,6E)-2,6-dimethyl-8-(oxan-2-yloxy)octa-2,6-dienyl] 2,2-dimethylpropanoate
  参考文献：
  名称：

  Synthesis of (1S,2R,12S)-2-hydroxy-11-dihydroneocembrene

  摘要：

  Aiming at the asymmetric total synthesis of trinervitane-type diterpenes, an efficient synthetic route to the title compound was explored starting from the THP ether of pivaloyloxy geraniol 11e. The coupling reaction with Grignard reagent 14 bearing the stereogenic carbon proceeded smoothly to give the THP ether of (11S)-10-dihydrogeranylgeraniol 10. Conversion to the corresponding acid chloride through the intermediate 9, followed by cyclization, afforded the dihydrocembrene derivative 8, from which the title compound 7 was prepared. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00376-6

文献信息

• Synthesis of (1S,2R,12S)-2-hydroxy-11-dihydroneocembrene
  作者：Tadahiro Kato、Shin-ichi Ebihara、Tohru Furukawa、Hirota Tanahashi、Masahiro Hoshikawa

  DOI：10.1016/s0957-4166(99)00376-6

  日期：1999.9

  Aiming at the asymmetric total synthesis of trinervitane-type diterpenes, an efficient synthetic route to the title compound was explored starting from the THP ether of pivaloyloxy geraniol 11e. The coupling reaction with Grignard reagent 14 bearing the stereogenic carbon proceeded smoothly to give the THP ether of (11S)-10-dihydrogeranylgeraniol 10. Conversion to the corresponding acid chloride through the intermediate 9, followed by cyclization, afforded the dihydrocembrene derivative 8, from which the title compound 7 was prepared. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.