(2E,6E,11S,14R)-14-(2-chloropropan-2-yl)-3,7,11-trimethylcyclotetradeca-2,6-dien-1-one | 254742-30-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2E,6E,11S,14R)-14-(2-chloropropan-2-yl)-3,7,11-trimethylcyclotetradeca-2,6-dien-1-one
• CAS: 254742-30-8
• 化学式: C₂₀H₃₃ClO
• 分子量: 324.934
• InChiKey: WNPGYHDYSSCWFM-QMMAFDQVSA-N

物化性质

• 沸点：
  431.2±34.0 °C(Predicted)
• 密度：
  0.932±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2E,6E,11S,14R)-14-(2-chloropropan-2-yl)-3,7,11-trimethylcyclotetradeca-2,6-dien-1-one 在 正丁基锂 、 silica gel 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 49.0h， 生成 (1S,2E,6E,11S,14S)-3,7,11-trimethyl-14-prop-1-en-2-ylcyclotetradeca-2,6-dien-1-ol
  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 、 sodium chlorite 、 sodium dihydrogenphosphate 、 氯化亚砜 、 碘 、 四氯化锡 、 potassium carbonate 、 戴斯-马丁氧化剂 、 对甲苯磺酸 、 magnesium 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 、 乙腈 、 苯 为溶剂， 反应 54.83h， 生成 (2E,6E,11S,14R)-14-(2-chloropropan-2-yl)-3,7,11-trimethylcyclotetradeca-2,6-dien-1-one
  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.