2-(1-methoxycarbonylindol-3-yl)acetonitrile | 115610-85-0

• 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: 2-(1-methoxycarbonylindol-3-yl)acetonitrile
• 英文别名: (1-carbomethoxy-1H-indol-3-yl)acetonitrile；methyl 3-(cyanomethyl)indole-1-carboxylate
• CAS: 115610-85-0
• 化学式: C₁₂H₁₀N₂O₂
• 分子量: 214.224
• InChiKey: TXQDKALLAHDYAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-methoxycarbonylindol-3-yl)acetonitrile 在 叔丁胺 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以100%的产率得到吲哚-3-乙腈
  参考文献：
  名称：

  t -BuNH 2从氨基甲酸酯上裂解烷氧基羰基保护基

  摘要：

  描述了一种有效，简单的方案，用于通过t -BuNH 2 / MeOH选择性裂解各种N-烷氧基羰基保护基。探索了该程序的范围，以研究一系列含有其他潜在反应性官能团的吲哚，苯胺和吡咯烷氨基甲酸酯衍生物，从而提供了氨基甲酸酯基团的清晰裂解。

  DOI：

  10.1016/j.tetlet.2006.11.024
• 作为产物：
  描述：

  吲哚-3-乙腈 、 氯甲酸甲酯 在 sodium hydride 作用下， 反应 24.0h， 以73%的产率得到2-(1-methoxycarbonylindol-3-yl)acetonitrile
  参考文献：
  名称：

  Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products

  摘要：

  This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.01.036

文献信息

• Enantioselective Michael Additions to α,β-Unsaturated Imides Catalyzed by a Salen−Al Complex
  作者：Mark S. Taylor、Eric N. Jacobsen

  DOI：10.1021/ja037177o

  日期：2003.9.1

  conjugate addition of di- and trisubstituted nitriles to a wide range of acyclic alkyl- and aryl-substituted α,β-unsaturated imides. This new methodology provides access to multifunctional compounds that previously have not been readily accessible in enantioenriched form. Synthetic applications of these products include the preparation of enantiomerically enriched piperidines, as exemplified by an expedient

  (Salen) 铝配合物 1b 是一种有效的催化剂，用于将二取代和三取代腈与各种无环烷基和芳基取代的 α,β-不饱和酰亚胺共轭加成。这种新方法提供了对以前不容易以对映体富集形式获得的多功能化合物的访问。这些产品的合成应用包括制备富含对映异构体的哌啶，例如 (-)-帕罗西汀的不对称催化合成。
• NMR studies of indoles and theirN-carboalkoxy derivatives
  作者：M. S. Morales-Ríos、P. Joseph-Nathan

  DOI：10.1002/mrc.1260251016

  日期：1987.10

  The 13C NMR assignment of indoles and 5‐methoxyindoles substituted at position 3, and some of their N‐carboalkoxy derivatives, was achieved from one‐ and two‐dimensional NMR experiments. Substituent chemical shifts and 1 J(CH) values were evaluated. The dynamic processes of N‐carboalkoxyindoles and N‐carboalkoxyindoline observed by high‐field 1H NMR show the existence of two preferred rotamers around

  3位取代的吲哚和5-甲氧基吲哚及其一些N-碳烷氧基衍生物的13C NMR归属是通过一维和二维NMR实验实现的。评估了取代基化学位移和 1 J(CH) 值。通过高场 1H NMR 观察到的 N-carboalkoxyindoles 和 N-carboalkoxyindoline 的动态过程表明在氨基甲酸酯 NC( O)OR 键周围存在两个优选的旋转异构体，这被解释为频率/场强依赖性现象。
• Morales-Rios, Martha S.; Bucio-Vasquez, Ma. Alvina; Joseph-Nathan, Pedro, Journal of Heterocyclic Chemistry, 1993, vol. 30, # 4, p. 953 - 956
  作者：Morales-Rios, Martha S.、Bucio-Vasquez, Ma. Alvina、Joseph-Nathan, Pedro

  DOI：——

  日期：——
• Cleavage of alkoxycarbonyl protecting groups from carbamates by t-BuNH2
  作者：Oscar R. Suárez-Castillo、Luis Alberto Montiel-Ortega、Myriam Meléndez-Rodríguez、Maricruz Sánchez-Zavala

  DOI：10.1016/j.tetlet.2006.11.024

  日期：2007.1

  An efficient, simple protocol for the selective cleavage of a variety of N-alkoxycarbonyl protecting groups by t-BuNH2/MeOH is described. The scope of the procedure was explored for a series of indole, aniline and pyrrolidine carbamate derivatives containing other potentially reactive functional groups affording a clean cleavage of the carbamate group.

  描述了一种有效，简单的方案，用于通过t -BuNH 2 / MeOH选择性裂解各种N-烷氧基羰基保护基。探索了该程序的范围，以研究一系列含有其他潜在反应性官能团的吲哚，苯胺和吡咯烷氨基甲酸酯衍生物，从而提供了氨基甲酸酯基团的清晰裂解。
• Preparation of 3-hydroxyoxindoles with dimethyldioxirane and their use for the synthesis of natural products
  作者：Oscar R. Suárez-Castillo、Maricruz Sánchez-Zavala、Myriam Meléndez-Rodríguez、Luis E. Castelán-Duarte、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.1016/j.tet.2006.01.036

  日期：2006.3

  This work describes a general protocol for the oxidation of indole and oxindole derivatives with dimethyldioxirane to give 3-hydroxyoxindoles present in many natural products. This strategy allowed us to synthesize the natural product 1, to carry out the first total synthesis of 4, a formal total synthesis of donaxaridine (5) and to achieve the synthesis of pyrroloindoline 8, a debromo analogue of the natural product flustraminol B (7). (c) 2006 Elsevier Ltd. All rights reserved.