3-(1-methyl-1H-indol-3-yl)acrylonitrile | 24662-35-9

• 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-(1-methyl-1H-indol-3-yl)acrylonitrile
• 英文别名: 3-(1-methyl-1H-indol-3-yl)prop-2-enenitrile；3-(1-methylindol-3-yl)prop-2-enenitrile
• CAS: 24662-35-9
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: UJPGLHAIWIZHGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(1-methyl-1H-indol-3-yl)acrylonitrile 在 镍 氢气 作用下， 以 甲醇 为溶剂， 生成 3-(1-methyl-1H-indol-3-yl)propyl-1-amine
  参考文献：
  名称：

  Highly potent inhibitors of the Grb2-SH2 domain

  摘要：

  Highly potent inhibitors of the Grb2-SH2 domain have been synthesized. They share the common sequence: Ac-Pmp-Ac(6)c-Asn-NH-(3-indolyl-propyl). Different substituents at the 3-indolyl-propylamine C-terminal group were explored to further improve the activity. This is the first example of inhibitors of SH2 domains with sub-nanomolar affinity reported to date. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00701-x
• 作为产物：
  描述：

  3-(dimethylamino)-3-(1-methyl-1H-indol-3-yl)propanenitrile 在 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 8.0h， 以98%的产率得到3-(1-methyl-1H-indol-3-yl)acrylonitrile
  参考文献：
  名称：

  一种两步合成3-(2-氰基乙烯基)吲哚衍生物的方法

  摘要：

  本发明公开了一种通过两步反应合成3‑(2‑氰基乙烯基)吲哚衍生物的方法。第一步反应：以廉价易得、具有结构多样性的吲哚衍生物为原料与3‑二甲胺基丙烯腈在酸存在下进行Friedel‑Crafts反应，合成3‑(1‑二甲胺基‑2‑氰基乙基)‑吲哚衍生物。第二步反应：以3‑(1‑二甲胺基‑2‑氰基乙基)‑吲哚衍生物为原料，使其在酸存在下发生自身分解反应，合成3‑(2‑氰基乙烯基)吲哚衍生物。与已报道的3‑(2‑氰基乙烯基)吲哚衍生物合成方法相比较，本发明原料廉价易得、毒性低、操作简便、合成反应条件温和以及效率高。

  公开号：

  CN108610276A

文献信息

• Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step
  作者：Yu-Jie Wang、Chen-Hui Yuan、De-Zhao Chu、Lei Jiao

  DOI：10.1039/d0sc02246b

  日期：——

  Ligand-enabled switch of the regioselectivity-determining step allowed for efficient regiocontrol in the aerobic oxidative Heck reaction of indole.

  通过配体促进的选择性决定步骤的转换，实现了对吲哚的空气氧化Heck反应的高效区域控制。
• Expedient synthesis of densely substituted pyrrolo[1,2-a]indoles
  作者：Dattatraya H. Dethe、Raghavender Boda

  DOI：10.1039/c6ob00861e

  日期：——

  indolyl-2-carbinols with various dienophiles such as indole derived α,β-unsaturated esters, ketones, nitriles and cinnamates is described. The strategy was further applied for the synthesis of optically active pyrrolo[1,2-a]indoles in >97% de using the chiral auxiliary based approach.

  描述了Cu（OTf）2催化吲哚基-2-甲醇与各种双亲物如吲哚衍生的α，β-不饱和酯，酮，腈和肉桂酸酯的[6 + 2]环加成反应。该策略进一步被应用到基于手性助剂的合成中，以> 97％de的光学活性吡咯并[1,2- a ]吲哚合成。
• Catalytic sp³C–CN Bond Cleavage: Ni-Mediated Phosphorylation of Alkylnitriles
  作者：Ji-Shu Zhang、Tieqiao Chen、Yongbo Zhou、Shuang-Feng Yin、Li-Biao Han

  DOI：10.1021/acs.orglett.8b02854

  日期：2018.11.2

  catalyst is disclosed. A wide range of primary nitriles readily coupled with secondary phosphine oxides to produce the corresponding phosphorylated products in high yields. As a key step, this new method was applied to the synthesis of anticancer drug Combretastatin-A4, significantly shortening its synthetic path.

  公开了由镍催化剂催化的sp 3 C-CN键的直接磷酸化。广泛的伯腈易于与仲膦氧化物偶联，以高收率生产相应的磷酸化产物。作为关键步骤，该新方法被应用于抗癌药Combretastatin-A4的合成，大大缩短了其合成途径。
• Construction of benzo[a]carbazole derivatives via Diels–Alder reaction of arynes with vinylindoles
  作者：Lijun Wu、Hui Huang、Pan Dang、Yun Liang、Shaofeng Pi

  DOI：10.1039/c5ra11025d

  日期：——

  A new protocol for a highly efficienct and versatile Diels–Alder reaction of vinylindoles with arynes (generated form 2-(trimethylsilyl)aryl triflate) has been developed. Various functionalized benzo[a]carbazoles were afforded in good to perfect yields via [4 + 2] cycloaddition/aromatization.

  已经开发出一种新的协议，用于乙烯基吲哚与芳烃的高效狄斯-阿尔德反应（生成形式为2-（三甲基甲硅烷基）芳基三氟甲磺酸酯）。通过[4 + 2]环加成/芳构化，可以提供各种官能化的苯并[ a ]咔唑，收率良好至理想。
• PHENYLPYRIDO [1,2-A] INDOLIUM-DERIVED THIOL/DISULFIDE DYE, DYE COMPOSITION COMPRISING THIS DYE, PROCESS FOR LIGHTENING KERATIN MATERIALS USING THIS DYE
  申请人：GREAVES Andrew

  公开号：US20120266392A1

  公开（公告）日：2012-10-25

  The invention relates to the dyeing of keratin materials using phenylpyrido[1,2-a]indolinium-derived thiol and disulfide fluorescent dyes. The invention relates to a dye composition comprising a phenylpyrido[1,2-a]indolinium-derived-chromophore thiol or disulfide dye and to a dyeing process with a lightening effect on keratin materials, in particular keratin fibers, especially human keratin fibers, such as the hair, using said composition. It similarly relates to novel phenylpyrido[1,2-a]indolinium-derived-chromophore thiol dyes and to the uses thereof in lightening keratin materials. This composition makes it possible to obtain a coloring with a lightening effect which is particularly resistant and visible on dark keratin fibers.

  本发明涉及使用苯基吡咯[1,2-a]吲哚基硫醇和二硫化物荧光染料染色角蛋白质材料。本发明涉及一种染料组成物，包括苯基吡咯[1,2-a]吲哚基色团硫醇或二硫化物染料，并且涉及使用该组成物对角蛋白质材料进行染色过程，特别是角蛋白质纤维，尤其是人类角蛋白质纤维，如头发，具有美白效果。它同样涉及新的苯基吡咯[1,2-a]吲哚基色团硫醇染料及其在美白角蛋白质材料方面的应用。该组成物可使得在深色角蛋白质纤维上获得特别耐用和明显的美白效果。