[(2S,3R,4S,5R,6R)-2-[[(1R,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2,4,6,8,10,15-hexaen-18-yl]oxy]-3,5-bis(2,2,2-trichloroethoxycarbonyloxy)-6-(2,2,2-trichloroethoxycarbonyloxymethyl)oxan-4-yl] 2,2,2-trichloroethyl carbonate | 485816-38-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2S,3R,4S,5R,6R)-2-[[(1R,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2,4,6,8,10,15-hexaen-18-yl]oxy]-3,5-bis(2,2,2-trichloroethoxycarbonyloxy)-6-(2,2,2-trichloroethoxycarbonyloxymethyl)oxan-4-yl] 2,2,2-trichloroethyl carbonate
• CAS: 485816-38-4
• 化学式: C₃₈H₃₂Cl₁₂N₂O₁₆
• 分子量: 1198.11
• InChiKey: VTAYOSYBLHCBEP-PMNNWGLQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  68
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  203
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  [(2S,3R,4S,5R,6R)-2-[[(1R,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2,4,6,8,10,15-hexaen-18-yl]oxy]-3,5-bis(2,2,2-trichloroethoxycarbonyloxy)-6-(2,2,2-trichloroethoxycarbonyloxymethyl)oxan-4-yl] 2,2,2-trichloroethyl carbonate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 、 锌 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 OPHR-23
  参考文献：
  名称：

  Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila

  摘要：

  Hairy roots of Ophiorrhiza pumila, a rubiaceous camptothecin-producing plant, were obtained. From an investigation of the secondary metabolites, it was found that the hairy roots produced camptothecin and its related alkaloids, i.e. (3S)-pumiloside, (3S)- and (3R)-deoxypumilosides and strictosamide. We also isolated two new camptothecinoids, OPHR-23 and OPHR-17, the structures of which including the absolute configurations, were determined by spectroscopic analyses and chemical conversion from tryptamine and secologanin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01196-1
• 作为产物：
  描述：

  (3R)-deoxypumiloside tetraacetate 在 吡啶 、 4-二甲氨基吡啶 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 19.5h， 生成 [(2S,3R,4S,5R,6R)-2-[[(1R,18S,19R,20S)-19-ethenyl-14-oxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-2,4,6,8,10,15-hexaen-18-yl]oxy]-3,5-bis(2,2,2-trichloroethoxycarbonyloxy)-6-(2,2,2-trichloroethoxycarbonyloxymethyl)oxan-4-yl] 2,2,2-trichloroethyl carbonate
  参考文献：
  名称：

  Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila

  摘要：

  Hairy roots of Ophiorrhiza pumila, a rubiaceous camptothecin-producing plant, were obtained. From an investigation of the secondary metabolites, it was found that the hairy roots produced camptothecin and its related alkaloids, i.e. (3S)-pumiloside, (3S)- and (3R)-deoxypumilosides and strictosamide. We also isolated two new camptothecinoids, OPHR-23 and OPHR-17, the structures of which including the absolute configurations, were determined by spectroscopic analyses and chemical conversion from tryptamine and secologanin. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01196-1

文献信息

• Camptothecin-related alkaloids from hairy roots of Ophiorrhiza pumila
  作者：Mariko Kitajima、Satoshi Yoshida、Kyoko Yamagata、Mio Nakamura、Hiromitsu Takayama、Kazuki Saito、Hiroko Seki、Norio Aimi

  DOI：10.1016/s0040-4020(02)01196-1

  日期：2002.11

  Hairy roots of Ophiorrhiza pumila, a rubiaceous camptothecin-producing plant, were obtained. From an investigation of the secondary metabolites, it was found that the hairy roots produced camptothecin and its related alkaloids, i.e. (3S)-pumiloside, (3S)- and (3R)-deoxypumilosides and strictosamide. We also isolated two new camptothecinoids, OPHR-23 and OPHR-17, the structures of which including the absolute configurations, were determined by spectroscopic analyses and chemical conversion from tryptamine and secologanin. (C) 2002 Elsevier Science Ltd. All rights reserved.