(Z)-(R)-11-{tert-Butoxycarbonyl-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-amino}-tetradec-5-enoic acid | 189251-27-2

• 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: (Z)-(R)-11-{tert-Butoxycarbonyl-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-amino}-tetradec-5-enoic acid
• 英文别名: (Z,11R)-11-[2-[tert-butyl(dimethyl)silyl]oxyethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]tetradec-5-enoic acid
• CAS: 189251-27-2
• 化学式: C₂₇H₅₃NO₅Si
• 分子量: 499.807
• InChiKey: HTKSTQNZCFSKSP-GQZPPLQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.79
• 重原子数：
  34.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  76.07
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (Z)-(R)-11-{tert-Butoxycarbonyl-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-amino}-tetradec-5-enoic acid 在 四丁基氟化铵 、 2-氯-1-甲基吡啶碘化物 、 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 6.0h， 生成 (Z)-(R)-15-Oxo-5-propyl-1-oxa-4-aza-cyclopentadec-10-ene-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Absolute configuration of insect-produced epilachnene

  摘要：

  Samples of (R) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en-14-olide] were synthesized from (R) and(S)-norvaline. The diastereomeric alpha-methoxy-alpha-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) alpha-methoxy-alpha-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00490-5
• 作为产物：
  描述：

  di(pent-4-enyl)magnesium 在 copper(l) iodide 、 双(三甲基硅烷基)氨基钾 、 sodium naphthalenide 、 sodium hydride 、 臭氧 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 44.67h， 生成 (Z)-(R)-11-{tert-Butoxycarbonyl-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-amino}-tetradec-5-enoic acid
  参考文献：
  名称：

  Absolute configuration of insect-produced epilachnene

  摘要：

  Samples of (R) and (S)-epilachnene [(5Z)-11-propyl-12-azacyclotetradec-5-en-14-olide] were synthesized from (R) and(S)-norvaline. The diastereomeric alpha-methoxy-alpha-trifluoromethylphenylacetyl amides of these synthetic samples, prepared using (S) alpha-methoxy-alpha-trifluoromethylphenylacetyl chloride, were well resolved by gas chromatography. Analogous derivatization and gas chromatographic analysis of a sample of epilachnene from the pupal secretion of the coccinellid beetle, Epilachna varivestis, established that the natural product is (S)-epilachnene. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00490-5