Mitomycin A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Mitomycin A
• 英文别名: (C-6-CH3-(2)H3)Mitomycin A；[(4S,6S,7R,8S)-7,11-dimethoxy-10,13-dioxo-12-(trideuteriomethyl)-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(9),11-dien-8-yl]methyl carbamate
• 化学式: C₁₆H₁₉N₃O₆
• 分子量: 352.32
• InChiKey: HYFMSAFINFJTFH-YMLCJLRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  7,7-(Ethylenedioxy)-6-(phenylseleno)mitosane 在 三乙基硼 、 三正丁基氢锡 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 正己烷 、 二氯甲烷 、 氯仿 、 丙酮 、 苯 为溶剂， 反应 105.5h， 生成 Mitomycin A
  参考文献：
  名称：

  First synthesis of mitomycins completely labeled at the C-6-methyl by 13CH3 and CD3

  摘要：

  The C-6-methyl group of mitomycins was completely labeled with carbon-13 or deuterium for the first time. The synthesis was accomplished by the C-6-methylation of 6-demethyl-7,7-(ethylenedioxy)-6-(phenylseleno)mitosane 8 that was formed by a novel replacement of the methylene moiety of 6-demethyl-7,7-(ethylenedioxy)-6-methylenemitosane 10 by a phenylseleno group, and followed by conversion to the mitomycins. For the synthesis of 8, we found that selenenamide 11 is an excellent reagent for the replacement. We have also determined that the replacement proceeded via the addition of 11 to the methylene of 10 with a subsequent retro-Mannich reaction.

  DOI：

  10.1021/jo00056a022

文献信息

• First synthesis of mitomycins completely labeled at the C-6-methyl by 13CH3 and CD3
  作者：Hitoshi Arai、Yutaka Kanda、Masaji Kasai

  DOI：10.1021/jo00056a022

  日期：1993.2

  The C-6-methyl group of mitomycins was completely labeled with carbon-13 or deuterium for the first time. The synthesis was accomplished by the C-6-methylation of 6-demethyl-7,7-(ethylenedioxy)-6-(phenylseleno)mitosane 8 that was formed by a novel replacement of the methylene moiety of 6-demethyl-7,7-(ethylenedioxy)-6-methylenemitosane 10 by a phenylseleno group, and followed by conversion to the mitomycins. For the synthesis of 8, we found that selenenamide 11 is an excellent reagent for the replacement. We have also determined that the replacement proceeded via the addition of 11 to the methylene of 10 with a subsequent retro-Mannich reaction.