1-methyl-2-demethyl-3'-N-methyl aplysinopsin

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-methyl-2-demethyl-3'-N-methyl aplysinopsin
• 化学式: C₁₅H₁₆N₄O
• 分子量: 268.318
• InChiKey: BBCALIHRTPPUQE-WQLSENKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  ethyl (Z)-3-(1-methylindol-3-yl)-2-[(triphenyl-lambda5-phosphanylidene)amino]prop-2-enoate 以 甲苯 为溶剂， 反应 45.0h， 生成 1-methyl-2-demethyl-3'-N-methyl aplysinopsin
  参考文献：
  名称：

  Iminophosphorane-mediated imidazole ring formation: A new and general entry to aplysinopsin-type alkaloids of marine origin.

  摘要：

  Aza Wittig-type reactions of iminophosphoranes 21, derived from ethyl alpha-azido-beta-(3-indolyl)propenoates and triphenylphosphine, with methyl isocyanate, carbon dioxide or carbon disulfide provide the corresponding heterocumulenes 22, 25 and 28 which undergo cyclization by the action of nitrogenous reagents completing the assemblage of the framework of aplysinopsin. Further deprotection leads to naturally occurring aplysinopsin analogues.

  DOI：

  10.1016/s0040-4020(01)85082-1

文献信息

• Iminophosphorane-mediated imidazole ring formation: A new and general entry to aplysinopsin-type alkaloids of marine origin.
  作者：Pedro Molina、Pedro Almendros、Pilar M. Fresneda

  DOI：10.1016/s0040-4020(01)85082-1

  日期：1994.2

  Aza Wittig-type reactions of iminophosphoranes 21, derived from ethyl alpha-azido-beta-(3-indolyl)propenoates and triphenylphosphine, with methyl isocyanate, carbon dioxide or carbon disulfide provide the corresponding heterocumulenes 22, 25 and 28 which undergo cyclization by the action of nitrogenous reagents completing the assemblage of the framework of aplysinopsin. Further deprotection leads to naturally occurring aplysinopsin analogues.