[(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-14-ethyl-6,10-dimethoxy-12-(methoxymethyl)-14-azapentacyclo[10.3.3.12,5.01,11.03,8]nonadecan-18-yl] acetate | 1264885-77-9

• 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: [(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-14-ethyl-6,10-dimethoxy-12-(methoxymethyl)-14-azapentacyclo[10.3.3.12,5.01,11.03,8]nonadecan-18-yl] acetate
• CAS: 1264885-77-9
• 化学式: C₃₀H₄₇NO₉
• 分子量: 565.704
• InChiKey: HJGJSKOIPGLIID-PLEHBQLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-14-ethyl-6,10-dimethoxy-12-(methoxymethyl)-14-azapentacyclo[10.3.3.12,5.01,11.03,8]nonadecan-18-yl] acetate 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以65%的产率得到[(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-6,10-dimethoxy-12-(methoxymethyl)-14-azapentacyclo[10.3.3.12,5.01,11.03,8]nonadec-13-en-18-yl] acetate
  参考文献：
  名称：

  Conversional studies towards taxoids from C₁₉-diterpenoid alkaloids by the BAC sequence

  摘要：

  The conversional synthesis of taxoids by the BAC sequence from the C19-diterpenoid alkaloids, 14-acetyltalatisamine (1), yunaconitine (12), and 14-acetylchasmanine (19), was designed and explored. Two aconane-type diterpenes 17 and 28, the advanced intermediates for our conversional synthesis, were synthesized. The key steps include the rupture of the C(7)-C(17) bond, the formation of imine, and the denitrogenation.

  DOI：

  10.1080/10286020.2010.510796
• 作为产物：
  描述：

  [(1R,2R,3S,4R,5S,6S,10S,11S,12R,18R)-4,5-diacetyloxy-14-ethyl-6,10-dimethoxy-12-(methoxymethyl)-14-azapentacyclo[10.3.3.12,5.01,11.03,8]nonadec-8-en-18-yl] acetate 在 10% palladium on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以100%的产率得到[(1R,2R,3R,4R,5S,6S,8S,10S,11S,12R,18R)-4,5-diacetyloxy-14-ethyl-6,10-dimethoxy-12-(methoxymethyl)-14-azapentacyclo[10.3.3.12,5.01,11.03,8]nonadecan-18-yl] acetate
  参考文献：
  名称：

  Conversional studies towards taxoids from C₁₉-diterpenoid alkaloids by the BAC sequence

  摘要：

  The conversional synthesis of taxoids by the BAC sequence from the C19-diterpenoid alkaloids, 14-acetyltalatisamine (1), yunaconitine (12), and 14-acetylchasmanine (19), was designed and explored. Two aconane-type diterpenes 17 and 28, the advanced intermediates for our conversional synthesis, were synthesized. The key steps include the rupture of the C(7)-C(17) bond, the formation of imine, and the denitrogenation.

  DOI：

  10.1080/10286020.2010.510796