20',20'-difluoro-4'-deoxyvinblastine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 长春花生物碱
• 英文名称: 20',20'-difluoro-4'-deoxyvinblastine
• 英文别名: 4'-Deoxy-20',20'-difluorovinblastine；methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-4-[(13S,15R,17R)-17-(1,1-difluoroethyl)-13-methoxycarbonyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9-tetraen-13-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
• 化学式: C₄₆H₅₆F₂N₄O₈
• 分子量: 830.969
• InChiKey: NOSAJPUYIASWEH-ODOBZBQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  60
• 可旋转键数：
  10
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  anhydrovinblastine 在 氯仿 、 氢氟酸 、 五氟化锑 作用下， 反应 0.33h， 以40%的产率得到20',20'-difluoro-4'-deoxyvinblastine
  参考文献：
  名称：

  On the Elucidation of the Mechanism ofVincaAlkaloid Fluorination in Superacidic Medium

  摘要：

  Detailed investigations on one of the key steps of the superacidic fluorination of Vinca alkaloids that is the origin of C20' activation are reported. While two different pathways can be envisioned for the emergence of the transient secondary carbocationic intermediate, isotopic labeling experiments unambiguously revealed the involvement of a 1,2-hydride shift mechanism.

  DOI：

  10.1021/ol201637m

文献信息

• VINORELBINE DERIVATIVES
  申请人：WOLF Mark A.

  公开号：US20080125451A1

  公开（公告）日：2008-05-29

  The present invention relates to novel vinorelbine derivatives. Pharmaceutical compositions containing these compounds as well as processes of preparation and processes of use for treatment of various conditions are also disclosed.
• VINCA DERIVATIVES
  申请人：WOLF Mark A.

  公开号：US20080119502A1

  公开（公告）日：2008-05-22

  The present invention relates to derivatives of vinca alkaloids. Pharmaceutical compositions containing these compounds as well as processes of preparation and treatment of various conditions are also disclosed.
• US8039453B2
  申请人：——

  公开号：US8039453B2

  公开（公告）日：2011-10-18
• On the Elucidation of the Mechanism of<i>Vinca</i>Alkaloid Fluorination in Superacidic Medium
  作者：Emerson Giovanelli、Sébastien Leroux、Lionel Moisan、Hélène Carreyre、Pierre Thuéry、David-Alexandre Buisson、Abdelkrim Meddour、Jean-Marie Coustard、Sébastien Thibaudeau、Bernard Rousseau、Marc Nicolas、Paul Hellier、Eric Doris

  DOI：10.1021/ol201637m

  日期：2011.8.5

  Detailed investigations on one of the key steps of the superacidic fluorination of Vinca alkaloids that is the origin of C20' activation are reported. While two different pathways can be envisioned for the emergence of the transient secondary carbocationic intermediate, isotopic labeling experiments unambiguously revealed the involvement of a 1,2-hydride shift mechanism.