leucomitomycin C | 92056-69-4

• 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: leucomitomycin C
• 英文别名: Mitomycin hydroquinone；[(4S,6S,7R,8S)-11-amino-10,13-dihydroxy-7-methoxy-12-methyl-2,5-diazatetracyclo[7.4.0.02,7.04,6]trideca-1(13),9,11-trien-8-yl]methyl carbamate
• CAS: 92056-69-4
• 化学式: C₁₅H₂₀N₄O₅
• 分子量: 336.348
• InChiKey: LCIXQLWPEFPXTH-WUDYKRTCSA-N

物化性质

• 沸点：
  578.6±50.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  153
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  leucomitomycin C 在 氧气 作用下， 以 乙醇 为溶剂， 生成 丝裂霉素 C
  参考文献：
  名称：

  Leucomitomycins

  摘要：

  DOI：

  10.1021/ja00333a056
• 作为产物：
  描述：

  丝裂霉素 C 在 palladium on activated charcoal 氢气 作用下， 以 氘代吡啶 为溶剂， 生成 leucomitomycin C
  参考文献：
  名称：

  Leucomitomycins

  摘要：

  DOI：

  10.1021/ja00333a056

文献信息

• Determination of the pKa Values for the Mitomycin C Redox Couple by Titration, pH Rate Profiles, and Nernst-Clark Fits. Studies of Methanol Elimination, Carbocation Formation, and the Carbocation/Quinone Methide Equilibrium
  作者：Romesh C. Boruah、Edward B. Skibo

  DOI：10.1021/jo00112a051

  日期：1995.4

  This report provides the results of a study of the mitomycin C (MMC) redox couple pK(a) values employing spectrophotometric titration, pH rate profiles, and Nernst-Clark plots. Oxidized mitomycin C (MMC(OX)) has three acid dissociations: pK(a1) = -1.2 for the protonated quinone, pK(a2) = 2.7 for the protonated indoline nitrogen, and pK(a3) = 7.6 for the protonated aziridino nitrogen. Two-electron reduction to MMC(red) results in a shift to higher pK(a) values: pK(a1) = 1.4 for the protonated 7-amino group, pK(a2) = 5.1 to 6.1 for the protonated indoline nitrogen, and pK,B = 9.1 for the protonated aziridino nitrogen. These pK(a) values were successfully integrated into previous mechanistic studies. The general conclusions are that indoline nitrogen protonation prevents methanol elimination, that methanol elimination from MMC(OX) and MMC(red) are both specific acid catalyzed, and that there is a 100000-fold increase in the second-order rate constant for specific acid-catalyzed elimination of methanol upon reduction of MMC(OX) to MMC(red). Finally, the formation and fate of the mitosene hydroquinone carbocation was studied in a mitosene model bearing an acetate leaving group. The carbocation species undergoes acid dissociation to the quinone methide (pK(a) = 7.1) resulting in a pH dependence for product formation. Below pH 7.1 the carbocation species traps water and above this pH the quinone methide species traps both water and a proton.
• Leucomitomycins
  作者：Samuel Danishefsky、Marco Ciufolini

  DOI：10.1021/ja00333a056

  日期：1984.10