1a-Acetyl-7-demethoxy-6-demethyl-7,7-(ethylenedioxy)-6,7-dihydro-6,6-bis((p-nitrophenyl)thio)mitomycin A | 155258-44-9

• 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: 1a-Acetyl-7-demethoxy-6-demethyl-7,7-(ethylenedioxy)-6,7-dihydro-6,6-bis((p-nitrophenyl)thio)mitomycin A
• 英文别名: [(4'S,6'S,7'R,8'S)-5'-acetyl-7'-methoxy-12',12'-bis[(4-nitrophenyl)sulfanyl]-10',13'-dioxospiro[1,3-dioxolane-2,11'-2,5-diazatetracyclo[7.4.0.02,7.04,6]tridec-1(9)-ene]-8'-yl]methyl carbamate
• CAS: 155258-44-9
• 化学式: C₃₀H₂₇N₅O₁₂S₂
• 分子量: 713.703
• InChiKey: CBNQOWVYZAKYIG-JHUDTCSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  49
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  280
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  1a-Acetyl-7-demethoxy-6-demethyl-7,7-(ethylenedioxy)-6,7-dihydro-6,6-bis((p-nitrophenyl)thio)mitomycin A 在 氨 、 5,5-二甲基-1,3-环己二酮 作用下， 以 甲醇 为溶剂， 反应 1.25h， 以27%的产率得到6-Demethyl-6-((p-nitrophenyl)thio)mitomycin C
  参考文献：
  名称：

  6-Demethyl-6-halo- and 6-Demethyl-6-thiomitomycins: Synthesis of Novel Mitomycin Derivatives Involving a Tandem Michael Addition/Retro-Mannich Reaction Sequence

  摘要：

  Synthesis of novel 6-demethyl-6-halomitomycins (3, 4, 6, and 7) and 6-demethyl-6-thiomitomycins (5 and 8) is described from key intermediates, namely, 6-demethyl-7,7-(ethylenedioxy)-6,6-dihalo- 6,7-dihydromitosanes (18 and 19) and 6-demethyl-7,7- (ethylenedioxy)-6,7-dihydro-6-thiomitosane (20), respectively. Compounds 18-20 were prepared through a tandem Michael addition and a retro-Mannich reaction sequence (N-halosuccinimide or cationic arylsulfenyl species in the presence of Et(2)NH) on 10.

  DOI：

  10.1021/jo00084a028
• 作为产物：
  描述：

  4,4'-二硝基二苯二硫醚 在 氯 、 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 1a-Acetyl-7-demethoxy-6-demethyl-7,7-(ethylenedioxy)-6,7-dihydro-6,6-bis((p-nitrophenyl)thio)mitomycin A
  参考文献：
  名称：

  6-Demethyl-6-halo- and 6-Demethyl-6-thiomitomycins: Synthesis of Novel Mitomycin Derivatives Involving a Tandem Michael Addition/Retro-Mannich Reaction Sequence

  摘要：

  Synthesis of novel 6-demethyl-6-halomitomycins (3, 4, 6, and 7) and 6-demethyl-6-thiomitomycins (5 and 8) is described from key intermediates, namely, 6-demethyl-7,7-(ethylenedioxy)-6,6-dihalo- 6,7-dihydromitosanes (18 and 19) and 6-demethyl-7,7- (ethylenedioxy)-6,7-dihydro-6-thiomitosane (20), respectively. Compounds 18-20 were prepared through a tandem Michael addition and a retro-Mannich reaction sequence (N-halosuccinimide or cationic arylsulfenyl species in the presence of Et(2)NH) on 10.

  DOI：

  10.1021/jo00084a028