ethyl α-azido-β-(N-methoxymethyl-3-indolyl)propenoate | 146336-95-0

• 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: ethyl α-azido-β-(N-methoxymethyl-3-indolyl)propenoate
• 英文别名: ethyl (Z)-2-azido-3-[1-(methoxymethyl)indol-3-yl]prop-2-enoate
• CAS: 146336-95-0
• 化学式: C₁₅H₁₆N₄O₃
• 分子量: 300.317
• InChiKey: HPJNYNGWPJEKHC-JYRVWZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl α-azido-β-(N-methoxymethyl-3-indolyl)propenoate 在 甲酸 作用下， 以 甲苯 为溶剂， 生成 1-(2-quinolyl)-9H-pyrido[3,4-b]indole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Iminophosphorane-mediated syntheses of the fascaplysin alkaloid of marine origin and nitramarine

  摘要：

  New and efficient syntheses of the fascaplysin alkaloid of marine origin and nitramarine are described. In both syntheses the key step, formation of the beta-carboline ring, involve a tandem aza-Wttig/electrocyclic ring closure process.

  DOI：

  10.1016/s0040-4039(00)78515-7
• 作为产物：
  描述：

  叠氮乙酸乙酯 、 1-(methoxymethyl)-1H-indole-3-carbaldehyde 生成 ethyl α-azido-β-(N-methoxymethyl-3-indolyl)propenoate
  参考文献：
  名称：

  Iminophosphorane-mediated syntheses of the fascaplysin alkaloid of marine origin and nitramarine

  摘要：

  New and efficient syntheses of the fascaplysin alkaloid of marine origin and nitramarine are described. In both syntheses the key step, formation of the beta-carboline ring, involve a tandem aza-Wttig/electrocyclic ring closure process.

  DOI：

  10.1016/s0040-4039(00)78515-7

文献信息

• An iminophosphorane-mediated efficient synthesis of the alkaloid eudistomin U of marine origin
  作者：Pedro Molina、Pilar M. Fresneda、Sagrario García-Zafra

  DOI：10.1016/0040-4039(95)00565-t

  日期：1995.5

  The first synthesis of the alkaloid eudistomin U, by a four-step sequence is described. The key step,formation of the beta-carboline ring, involves a tandem aza Wittig/electrocyclic ring closure process.
• 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.
• MOODY, C. J;WARD, J. G., J. CHEM. SOC. PERKIN TRANS., 1984, N 12, 2903-2909
  作者：MOODY, C. J、WARD, J. G.

  DOI：——

  日期：——
• Iminophosphorane-mediated syntheses of the fascaplysin alkaloid of marine origin and nitramarine
  作者：Pedro Molina、Pilar M. Fresneda、Sagrario García-Zafra、Pedro Almendros

  DOI：10.1016/s0040-4039(00)78515-7

  日期：1994.11

  New and efficient syntheses of the fascaplysin alkaloid of marine origin and nitramarine are described. In both syntheses the key step, formation of the beta-carboline ring, involve a tandem aza-Wttig/electrocyclic ring closure process.