1a-Acetyl-6,6-dibromo-7-demethoxy-6-demethyl-7,7-(ethylenedioxy)-6,7-dihydromitomycin A | 141936-31-4

• 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-6,6-dibromo-7-demethoxy-6-demethyl-7,7-(ethylenedioxy)-6,7-dihydromitomycin A
• 英文别名: [(4'S,6'S,7'R,8'S)-5'-acetyl-12',12'-dibromo-7'-methoxy-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: 141936-31-4
• 化学式: C₁₈H₁₉Br₂N₃O₈
• 分子量: 565.172
• InChiKey: FSWXMFPLZHWYFV-XOWOQMKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1a-Acetyl-6,6-dibromo-7-demethoxy-6-demethyl-7,7-(ethylenedioxy)-6,7-dihydromitomycin A 在 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 作用下， 以 甲醇 为溶剂， 反应 24.33h， 生成 [(4S,6S,7R,8S)-12-bromo-7,11,11-trimethoxy-10,13-dioxo-2,5-diazatetracyclo[7.4.0.02,7.04,6]tridec-1(9)-en-8-yl]methyl carbamate
  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：

  7,7-(Ethylenedioxy)-6-(phenylseleno)mitosane 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 、 二乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1a-Acetyl-6,6-dibromo-7-demethoxy-6-demethyl-7,7-(ethylenedioxy)-6,7-dihydromitomycin 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

文献信息

• 6-Demethyl-6-halo- and 6-Demethyl-6-thiomitomycins: Synthesis of Novel Mitomycin Derivatives Involving a Tandem Michael Addition/Retro-Mannich Reaction Sequence
  作者：Hitoshi Arai、Masaji Kasai

  DOI：10.1021/jo00084a028

  日期：1994.3

  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.