isomitomycin A | 91917-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: isomitomycin A
• 英文别名: [(3S,4S,7R,8S)-7,11-dimethoxy-12-methyl-10,13-dioxo-2,6-diazatetracyclo[7.4.0.02,4.03,7]trideca-1(9),11-dien-8-yl]methyl carbamate
• CAS: 91917-64-5
• 化学式: C₁₆H₁₉N₃O₆
• 分子量: 349.343
• InChiKey: YKXDGMVCESRRDO-VFWICMBZSA-N

物化性质

• 沸点：
  584.5±50.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 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：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  isomitomycin A 在 氨 作用下， 反应 5.0h， 以75%的产率得到丝裂霉素 C
  参考文献：
  名称：

  An efficient chemical conversion of mitomycin A to isomitomycin A

  摘要：

  After inspection of the X-ray crystallographic analyses of mitomycin A (1a) and albomitomycin A (2), an efficient chemical conversion of 1a to isomitomycin A (3) via 2 was accomplished in 68% overall yield. First ta was converted to (8aS)-8a-bromoalbomitomycin A (4b) in 89% yield, which was reduced with tributyltin hydride and AIBN to give 2 in 85% yield. Second, the C4a-N4 bond of 2 was selectively cleaved under hydrogenolysis conditions, and subsequent air oxidation afforded 3 in 90% yield from 2. Treatment of 2 or 3 with NH3 in methanol afforded mitomycin C (1b) in good yield.

  DOI：

  10.1021/jo00052a052
• 作为产物：
  描述：

  (8aS)-8a-bromoalbomitomycin A 在 palladium on activated charcoal 、 palladium on barium sulfate air 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 4.17h， 生成 isomitomycin A
  参考文献：
  名称：

  An efficient chemical conversion of mitomycin A to isomitomycin A

  摘要：

  After inspection of the X-ray crystallographic analyses of mitomycin A (1a) and albomitomycin A (2), an efficient chemical conversion of 1a to isomitomycin A (3) via 2 was accomplished in 68% overall yield. First ta was converted to (8aS)-8a-bromoalbomitomycin A (4b) in 89% yield, which was reduced with tributyltin hydride and AIBN to give 2 in 85% yield. Second, the C4a-N4 bond of 2 was selectively cleaved under hydrogenolysis conditions, and subsequent air oxidation afforded 3 in 90% yield from 2. Treatment of 2 or 3 with NH3 in methanol afforded mitomycin C (1b) in good yield.

  DOI：

  10.1021/jo00052a052

文献信息

• Albomitomycin A and isomitomycin A. products of novel intramolecular rearrangement of mitomycin A
  作者：Motomichi Kono、Yutaka Saitoh、Kunikatsu Shirahata、Yuko Arai、Shinzo Ishii

  DOI：10.1021/ja00257a072

  日期：1987.11
• J. Org. Chem. 1992, 57, 7296-7299
  作者：

  DOI：——

  日期：——
• FUKUYAMA, TOHRU;YANG, LIHU, J. AMER. CHEM. SOC., 111,(1989) N1, C. 8303-8304
  作者：FUKUYAMA, TOHRU、YANG, LIHU

  DOI：——

  日期：——
• An efficient chemical conversion of mitomycin A to isomitomycin A
  作者：Masaji Kasai、Motomichi Kono、Shunichi Ikeda、Nobuyuki Yoda、Noriaki Hirayama

  DOI：10.1021/jo00052a052

  日期：1992.12

  After inspection of the X-ray crystallographic analyses of mitomycin A (1a) and albomitomycin A (2), an efficient chemical conversion of 1a to isomitomycin A (3) via 2 was accomplished in 68% overall yield. First ta was converted to (8aS)-8a-bromoalbomitomycin A (4b) in 89% yield, which was reduced with tributyltin hydride and AIBN to give 2 in 85% yield. Second, the C4a-N4 bond of 2 was selectively cleaved under hydrogenolysis conditions, and subsequent air oxidation afforded 3 in 90% yield from 2. Treatment of 2 or 3 with NH3 in methanol afforded mitomycin C (1b) in good yield.