1,2,5-甲桥-1H,5H-咪唑并[2,1-i]吲哚-7,10-二酮,6-[[(氨基羰基)氧代]甲基]-2,3,6,6a-四氢-5,8-二甲氧基-9-甲基-,(1S,2S,4S,5R,6S,6aR,10aS,11S)-(9CI) | 110934-24-2

• 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
• 中文名称: 1,2,5-甲桥-1H,5H-咪唑并[2,1-i]吲哚-7,10-二酮,6-[[(氨基羰基)氧代]甲基]-2,3,6,6a-四氢-5,8-二甲氧基-9-甲基-,(1S,2S,4S,5R,6S,6aR,10aS,11S)-(9CI)
• 英文名称: albomitomycin A
• 英文别名: [(1S,3S,4S,7R,8S,9R)-7,11-dimethoxy-12-methyl-10,13-dioxo-2,6-diazapentacyclo[7.4.0.01,6.02,4.03,7]tridec-11-en-8-yl]methyl carbamate
• CAS: 110934-24-2
• 化学式: C₁₆H₁₉N₃O₆
• 分子量: 349.343
• InChiKey: LVZWYDBGPFFALC-FSCMACQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2,5-甲桥-1H,5H-咪唑并[2,1-i]吲哚-7,10-二酮,6-[[(氨基羰基)氧代]甲基]-2,3,6,6a-四氢-5,8-二甲氧基-9-甲基-,(1S,2S,4S,5R,6S,6aR,10aS,11S)-(9CI) 在 氨 作用下， 反应 0.5h， 以99%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 偶氮二异丁腈 、 三正丁基氢锡 、 potassium carbonate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 24.17h， 生成 1,2,5-甲桥-1H,5H-咪唑并[2,1-i]吲哚-7,10-二酮,6-[[(氨基羰基)氧代]甲基]-2,3,6,6a-四氢-5,8-二甲氧基-9-甲基-,(1S,2S,4S,5R,6S,6aR,10aS,11S)-(9CI)
  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

• 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.