colchicine

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: colchicine
• 英文别名: N-[(7S)-2,3,4,10-tetramethoxy-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]acetamide
• 化学式: C₂₂H₂₅NO₆
• 分子量: 399.444
• InChiKey: XXTCGVALMPUCBB-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  colchicine 、 2-甲基-6-亚硝基吡啶 以 甲醇 为溶剂， 以82%的产率得到N-[(1S,11S,13S)-5,6,7,15-tetramethoxy-17-(6-methylpyridin-2-yl)-14-oxo-18-oxa-17-azatetracyclo[11.3.2.02,12.03,8]octadeca-2(12),3,5,7,15-pentaen-11-yl]acetamide
  参考文献：
  名称：

  Retro iminonitroso Diels–Alder reactions: interconversion of nitroso cycloadducts

  摘要：

  Retro iminonitroso Diels-Alder reactions were investigated in both solution and solid phase. In thermal or Cu(I)-mediated reactions, interconversion of various nitroso cycloadducts occurred in the presence of separate dienes. Up to 99% of conversion was observed. Use of chiral ligands in the Cu(I)-mediated reactions gave new cycloadducts enantioselectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.121

文献信息

• Iminonitroso Diels−Alder Reactions for Efficient Derivatization and Functionalization of Complex Diene-Containing Natural Products
  作者：Fangzheng Li、Baiyuan Yang、Marvin J. Miller、Jaroslav Zajicek、Bruce C. Noll、Ute Möllmann、Hans-Martin Dahse、Patricia A. Miller

  DOI：10.1021/ol071322b

  日期：2007.7.1

  A remarkably efficient method for derivatization of complex diene-containing natural products by using stabilized iminonitroso Diels-Alder reactions is described. Turimycin H3, ergosterol, reductiomycin, isoforocidin, colchicine and thebaine were found to react with nitrosopyridines in a highly efficient regio- and stereoselective fashion. Preliminary bioactivity evaluations of turimycin cycloadducts are reported.
• Retro iminonitroso Diels–Alder reactions: interconversion of nitroso cycloadducts
  作者：Baiyuan Yang、Weimin Lin、Viktor Krchnak、Marvin J. Miller

  DOI：10.1016/j.tetlet.2009.07.121

  日期：2009.10

  Retro iminonitroso Diels-Alder reactions were investigated in both solution and solid phase. In thermal or Cu(I)-mediated reactions, interconversion of various nitroso cycloadducts occurred in the presence of separate dienes. Up to 99% of conversion was observed. Use of chiral ligands in the Cu(I)-mediated reactions gave new cycloadducts enantioselectively. (C) 2009 Elsevier Ltd. All rights reserved.