ethyl 3-cyano-1H-indole-2-carboxylate | 174094-24-7

• 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: ethyl 3-cyano-1H-indole-2-carboxylate
• 英文别名: ethyl 3-cyanoindol-2-carboxylate
• CAS: 174094-24-7
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: JGEIUCYFVXAGDV-UHFFFAOYSA-N

物化性质

• 沸点：
  444.3±30.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  ethyl 3-cyano-1H-indole-2-carboxylate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以85%的产率得到3-cyanoindol-2-carboxylic acid
  参考文献：
  名称：

  Indoles and pyridazino[4,5-b]indoles as nonnucleoside analog inhibitors of HIV-1 reverse transcriptase

  摘要：

  The synthesis and the study of the activity of new indol-2-carboxamides and pyridazino[4,5-b]indoles as inhibitors of HIV-1 reverse transcriptase (RT) are presented. The activity of the compounds synthesized as inhibitors of different types of HIV-1 RT (wild type enzyme and mutant forms P236L, Y181C and P236L/Y181C) was evaluated. The activity of the most active compounds was investigated in the syncytia reduction in vitro assay, in HIV-1(IIIB)-infected HT4lacZ-1 cells. Their potential cytotoxicity was determined in parallel. Two lead compounds, N-[1-[2-(3-isopropylamino)pyridyl]piperazin]-5,6-methylenedioxy indol-2-carboxamide 7q and N-[1-[2-(3-ethylamino)pyridyl]piperazin] 7s have been identified.

  DOI：

  10.1016/0223-5234(96)88316-4
• 作为产物：
  描述：

  3-甲酰基-1H-吲哚-2-羧酸乙酯 在 吡啶 、 盐酸羟胺 、 甲基磺酰氯 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 20.0h， 生成 ethyl 3-cyano-1H-indole-2-carboxylate
  参考文献：
  名称：

  抢救醋酸酐：通过Castagnoli-Cushman反应轻松获得特权的1,2,3,4-四氢吡嗪并[1,2- a ]吲哚核

  摘要：

  早先被认为在Castagnoli-Cushman与亚胺的反应中没有反应性的吲哚稠合的环状酸酐已成为该过程的有效参与者。新的反应形式包括使用各自的基于吲哚的二羧酸和后者通过乙酸酐的原位环脱水。这一发现证实了一种根本上新颖的合成化合物的方法，该方法基于特权的1,2,3,4-四氢吡嗪并[1,2- a ]吲哚核，其特征是迄今未描述的取代方式。

  DOI：

  10.1016/j.tetlet.2018.08.049

文献信息

• Pd(OAc)2-catalyzed C–H activation of indoles: a facile synthesis of 3-cyanoindoles
  作者：B.V. Subba Reddy、Zubeda Begum、Y. Jayasudhan Reddy、J.S. Yadav

  DOI：10.1016/j.tetlet.2010.04.086

  日期：2010.6

  Indoles undergo smooth cyanation with CuCN in the presence of 20 mol% Pd(OAc)(2) and 40 mol% CuBr2 in DMF to produce a wide range of the corresponding 3-cyanoindoles in good yields with high regioselectivity. (C) 2010 Elsevier Ltd. All rights reserved.
• N-Benzylindole-2-carboxylic acids: potent functional antagonists of the CCR2b chemokine receptor
  作者：Jason G. Kettle、Alan W. Faull、Andy J. Barker、D.Huw Davies、Michael A. Stone

  DOI：10.1016/j.bmcl.2003.10.049

  日期：2004.1

  Screening of the corporate database led to the discovery of a novel series of N-benzylindole-2-carboxylic acid CCR2b chemokine receptor antagonists. These compounds demonstrate high affinity and functional inhibition of the CCR2b receptor. A discussion of the structure-activity relationships is presented, together with evidence for a highly selective receptor binding profile. (C) 2003 Elsevier Ltd. All rights reserved.
• One-pot syntheses of 3-cyanoindoles from 3-acyl- and 3-ethoxycarbonyl-1,2-dihydrocinnoline-1,2-dicarboximides
  作者：Satoko Tanaka、Kazuyoshi Seguchi、Akira Sera

  DOI：10.1039/p19950000519

  日期：——

  2-Acyl- and 2-ethoxycarbonyl-3 cyanoindoles were prepared from 3-acyl- and 3-ethoxycarbonyl-1,2-dihydrocinnoline-1,2-dicarboximides and potassium cyanide via Michael addition, skeletal rearrangement and subsequent elimination of isocyanate.
• Acetic anhydride to the rescue: Facile access to privileged 1,2,3,4-tetrahydropyrazino[1,2-a]indole core via the Castagnoli-Cushman reaction
  作者：Maria Chizhova、Olesya Khoroshilova、Dmitry Dar'in、Mikhail Krasavin

  DOI：10.1016/j.tetlet.2018.08.049

  日期：2018.10

  Indole-fused cyclic anhydrides earlier deemed unreactive in the Castagnoli-Cushman reaction with imines have been rendered valid participant in this process. The new reaction format involves the use of respective indole-based dicarboxylic acids and in situ cyclodehydration of the latter by acetic anhydride. This finding validates a fundamentally new approach to synthesizing compounds based on the privileged

  早先被认为在Castagnoli-Cushman与亚胺的反应中没有反应性的吲哚稠合的环状酸酐已成为该过程的有效参与者。新的反应形式包括使用各自的基于吲哚的二羧酸和后者通过乙酸酐的原位环脱水。这一发现证实了一种根本上新颖的合成化合物的方法，该方法基于特权的1,2,3,4-四氢吡嗪并[1,2- a ]吲哚核，其特征是迄今未描述的取代方式。
• Indoles and pyridazino[4,5-b]indoles as nonnucleoside analog inhibitors of HIV-1 reverse transcriptase
  作者：M Font、A Monge、A Cuartero、A Elorriaga、J.J. Martínez-Irujo、E Alberdi、E Santiago、I Prieto、J.J. Lasarte、P Sarobe、F Borrás

  DOI：10.1016/0223-5234(96)88316-4

  日期：1995.1

  The synthesis and the study of the activity of new indol-2-carboxamides and pyridazino[4,5-b]indoles as inhibitors of HIV-1 reverse transcriptase (RT) are presented. The activity of the compounds synthesized as inhibitors of different types of HIV-1 RT (wild type enzyme and mutant forms P236L, Y181C and P236L/Y181C) was evaluated. The activity of the most active compounds was investigated in the syncytia reduction in vitro assay, in HIV-1(IIIB)-infected HT4lacZ-1 cells. Their potential cytotoxicity was determined in parallel. Two lead compounds, N-[1-[2-(3-isopropylamino)pyridyl]piperazin]-5,6-methylenedioxy indol-2-carboxamide 7q and N-[1-[2-(3-ethylamino)pyridyl]piperazin] 7s have been identified.