3-Cyan-3-(3-Indolyl)propionsaeure-ethylester | 10184-97-1

• 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: 3-Cyan-3-(3-Indolyl)propionsaeure-ethylester
• 英文别名: ethyl 3-cyano-3-(1H-indol-3-yl)propanoate；Ethyl-3-cyano-3-(3-indolyl)propionat；3-cyano-3-indol-3-yl-propionic acid ethyl ester；3-Cyan-3-indol-3-yl-propionsaeure-aethylester
• CAS: 10184-97-1
• 化学式: C₁₄H₁₄N₂O₂
• 分子量: 242.277
• InChiKey: GOTNBVYYMNYPJJ-UHFFFAOYSA-N

物化性质

• 熔点：
  110-111 °C(Solv: ethyl acetate (141-78-6); benzene (71-43-2))
• 沸点：
  446.2±35.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  65.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Cyan-3-(3-Indolyl)propionsaeure-ethylester 在 Raney Ni (W-4) sodium hydroxide 、 氢气 作用下， 反应 8.0h， 生成 4-amino-3-(indol-3-yl)butanoic acid
  参考文献：
  名称：

  Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers

  摘要：

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.

  DOI：

  10.1021/jm00348a022
• 作为产物：
  描述：

  3-吲哚甲醛 在 哌啶 、 乙醇 、 溶剂黄146 、 苯 作用下， 生成 3-Cyan-3-(3-Indolyl)propionsaeure-ethylester
  参考文献：
  名称：

  Notes: Convenient Syntheses of 3-Indolesuccinic and 3-Indolepropionic Acids

  摘要：

  DOI：

  10.1021/jo01090a631

文献信息

• Blaise reaction: synthesis, skeletal diversification of C(4) substituted 5-ylidenepyrrol-(5<i>H</i>)-ones and the role of the strategically located ester on the reactivity of the nitriles
  作者：H. Surya Prakash Rao、Ashiq Hussain Padder

  DOI：10.1039/d0nj00231c

  日期：——

  classical Blaise reaction. The products were further transformed to useful small organic molecules (SOMs). Studies on the reactivity of nitriles via intra and inter-molecular competition experiments showed that anchimeric assistance from the neighbouring and strategically located ester is crucial for higher reactivity of the nitrile in the 3-cyanopropionates towards the Blaise reaction.

  通过经典的布莱斯反应的有用变化，我们已经从3-芳基/杂芳基/烷基3-氰基丙酸酯和乙基/甲基溴乙酸酯中轻松合成了几个C（4）取代的5-亚吡咯烷基- （5 H）- 。将产物进一步转化为有用的有机小分子（SOM）。通过分子内和分子间竞争实验对腈的反应性进行的研究表明，邻位和关键位置的酯的邻氨基苯甲酸辅助对于3-氰基丙酸酯中腈对Blaise反应的更高反应性至关重要。
• Droste, Holger; Wieland, Theodor, Liebigs Annalen der Chemie, 1987, p. 901 - 910
  作者：Droste, Holger、Wieland, Theodor

  DOI：——

  日期：——
• KURCHACOVA, E.;SAFDY, M. E.
  作者：KURCHACOVA, E.、SAFDY, M. E.

  DOI：——

  日期：——
• US4333943A
  申请人：——

  公开号：US4333943A

  公开（公告）日：1982-06-08
• Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers
  作者：Max E. Safdy、Elva Kurchacova、Robert N. Schut、Horacio Vidrio、Enrique Hong

  DOI：10.1021/jm00348a022

  日期：1982.6

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.