ethyl (Z)-3-[1-(methoxymethyl)indol-3-yl]-2-[(triphenyl-lambda5-phosphanylidene)amino]prop-2-enoate | 146336-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl (Z)-3-[1-(methoxymethyl)indol-3-yl]-2-[(triphenyl-lambda5-phosphanylidene)amino]prop-2-enoate
• 英文别名: ethyl (Z)-3-[1-(methoxymethyl)indol-3-yl]-2-[(triphenyl-λ5-phosphanylidene)amino]prop-2-enoate
• CAS: 146336-96-1
• 化学式: C₃₃H₃₁N₂O₃P
• 分子量: 534.595
• InChiKey: CNNMJFKXWKTGIC-SXBRIOAWSA-N

物化性质

• 沸点：
  694.5±65.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  39
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (Z)-3-[1-(methoxymethyl)indol-3-yl]-2-[(triphenyl-lambda5-phosphanylidene)amino]prop-2-enoate 在 platinum(IV) oxide lithium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 生成 1-(2-Aminobenzoyl)-9-(methoxymethyl)pyrido[3,4-b]indole-3-carboxylic acid
  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：

  1-(methoxymethyl)-1H-indole-3-carbaldehyde 生成 ethyl (Z)-3-[1-(methoxymethyl)indol-3-yl]-2-[(triphenyl-lambda5-phosphanylidene)amino]prop-2-enoate
  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

• Iminophosphorane-mediated synthesis of 1-acyl-β-carbolines: A new access to the alkaloids eudistomin T, S and xestomanzamine A of marine origin
  作者：Pedro Molina、Pilar M Fresneda、Sagrario García-Zafra

  DOI：10.1016/s0040-4039(97)82962-0

  日期：1996.12

  described. The key step, formation of the 1-phenylacetyl β- carboline, involves a tandem aza Wittig / electrocyclic ring closure process. The first synthesis of the alkaloid xestomanzamine A is achieved by coupling of a N-protected harmane, now available via aza Wittig / electrocyclic ring closure process, with a 5-lithioimidazole derivative.

  描述了生物碱eudistomin T和S的新合成方法。关键步骤是形成1-苯基乙酰基β-咔啉，这涉及串联氮杂Wittig /电环闭合过程。生物碱异丁苯甲胺A的首次合成是通过将N-保护的harmane与5-lithioimidazole衍生物偶合（现在可通过aza Wittig /电环闭合工艺获得）。
• 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.