[(19S)-19-ethyl-12-hydroxy-7-(2-methylpropoxycarbonyloxy)-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl] 2-methylpropyl carbonate | 824396-00-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 喜树碱
• 英文名称: [(19S)-19-ethyl-12-hydroxy-7-(2-methylpropoxycarbonyloxy)-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl] 2-methylpropyl carbonate
• CAS: 824396-00-1
• 化学式: C₃₀H₃₂N₂O₁₀
• 分子量: 580.591
• InChiKey: BWOZIVXAZOUPAH-QNGSWNHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  151
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  [(19S)-19-ethyl-12-hydroxy-7-(2-methylpropoxycarbonyloxy)-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl] 2-methylpropyl carbonate 在 硫酸 作用下， 以90%的产率得到(19S)-19-ethyl-7,12,19-trihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione
  参考文献：
  名称：

  New Method for the Synthesis of 5‐Hydroxycamptothecin Derivatives

  摘要：

  An efficient hydroxylation at the 5-position of the C ring of camptothecins was accomplished with the complex of CuI and organic amines as catalyst in the presence of oxygen at room temperature in dimethyl formate (DMF). To be successfully hydroxylated. the insoluble camptothecin analogue was transformed to the corresponding 20 carbonates.

  DOI：

  10.1081/scc-200039356
• 作为产物：
  描述：

  10-羟基喜树碱 在 copper(l) iodide 氧气 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(19S)-19-ethyl-12-hydroxy-7-(2-methylpropoxycarbonyloxy)-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-19-yl] 2-methylpropyl carbonate
  参考文献：
  名称：

  New Method for the Synthesis of 5‐Hydroxycamptothecin Derivatives

  摘要：

  An efficient hydroxylation at the 5-position of the C ring of camptothecins was accomplished with the complex of CuI and organic amines as catalyst in the presence of oxygen at room temperature in dimethyl formate (DMF). To be successfully hydroxylated. the insoluble camptothecin analogue was transformed to the corresponding 20 carbonates.

  DOI：

  10.1081/scc-200039356

文献信息

• New Method for the Synthesis of 5‐Hydroxycamptothecin Derivatives
  作者：Xungui He、Heyong Gao、Wei Lu、Junchao Cai

  DOI：10.1081/scc-200039356

  日期：2004.12.31

  An efficient hydroxylation at the 5-position of the C ring of camptothecins was accomplished with the complex of CuI and organic amines as catalyst in the presence of oxygen at room temperature in dimethyl formate (DMF). To be successfully hydroxylated. the insoluble camptothecin analogue was transformed to the corresponding 20 carbonates.