(Z)-3-(1-methyl-1H-indol-3-yl)acrylonitrile | 68716-93-8

• 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: (Z)-3-(1-methyl-1H-indol-3-yl)acrylonitrile
• 英文别名: (Z)-3-(1-methylindol-3-yl)prop-2-enenitrile
• CAS: 68716-93-8
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: UJPGLHAIWIZHGD-PLNGDYQASA-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

• 作为产物：
  描述：

  (E)-3-(1-methylindol-3-yl)-2-methylsulfanylprop-2-enenitrile 生成 (Z)-3-(1-methyl-1H-indol-3-yl)acrylonitrile
  参考文献：
  名称：

  KANO S.; YOKOMMATSU T.; ONO J.; HIBINO S.; SHIBUYA S., CHEM. AND PHARM. BULL., 1978, 26, NO 6, 1874-1879

  摘要：

  DOI：

文献信息

• Brønsted Acid-Promoted Cascade Alkylation/Cyclization of Pyrroles with<i>N</i>,<i>N</i>-Dimethylaminomethyleneglutaconic Acid Dinitrile: A Concise Route to Cyclopenta[<i>b</i>]pyrroles
  作者：Kaikai Wu、Ping Wu、Jiping Chen、Chenglin Sun、Zhengkun Yu

  DOI：10.1002/adsc.201500546

  日期：2015.10.12

  A Brønsted acid (p-TsOH⋅H2O) promoted alkylation/cyclization cascade reaction of pyrroles with N,N-dimethylaminomethyleneglutaconic acid dinitrile was efficiently realized to afford functionalized cyclopenta[b]pyrroles with excellent diastereoselectivity. Deamination of the corresponding ammonium salts of the cyclopenta[b]pyrroles with methyl iodide led to dihydrocyclopenta[c]pyrroles. The cascade reaction

  有效地实现了布朗斯台德酸（p -TsOH·H 2 O）促进吡咯与N，N-二甲基氨基亚甲基戊二酸二腈的烷基化/环化级联反应，从而提供具有优异非对映选择性的官能化环戊[ b ]吡咯。环戊[ b ]吡咯的相应铵盐与甲基碘的脱氨基反应生成二氢环戊[ c ]吡咯。通过反应中间体，即2-烷基化吡咯的分离和转化，证实了级联反应途径。
• Tunable Brønsted Acidity-Dependent Alkylation and Alkenylation of Indoles
  作者：Kaikai Wu、Ping Wu、Liandi Wang、Jiping Chen、Chenglin Sun、Zhengkun Yu

  DOI：10.1002/adsc.201400477

  日期：2014.12.15

  AbstractThe Brønsted acid‐mediated alkylation and alkenylation of indoles were efficiently achieved by means of 3‐(dimethylamino)acrylonitrile. Regulating the acidity of the reaction medium with para‐toluenesulfonic acid monohydrate (p‐TsOH⋅H2O) and/or acetic acid (HOAc) led to versatile formation of 3‐alkylated and 3‐alkenylated indole derivatives under mild conditions. The 3‐alkylated indole products could be nearly quantitatively transformed to the corresponding separable (E)‐ and (Z)‐3‐alkenylated indoles.magnified image
• Palladium-Catalyzed α,β-Dehydrogenation of Esters and Nitriles
  作者：Yifeng Chen、Justin P. Romaire、Timothy R. Newhouse

  DOI：10.1021/jacs.5b02243

  日期：2015.5.13

  A highly practical and general palladium-catalyzed methodology for the alpha,beta-dehydrogenation of esters and nitriles is repotted. Generation of a zinc enolate or (cyanoalkyl)zinc species followed by the addition of an allyl oxidant and a palladium catalyst results in synthetically useful yields of alpha,beta-unsaturated esters, lactones, and nitriles. Preliminary mechanistic investigations are consistent with reversible beta-hydride elimination and turnover-limiting, propene-forming reductive elimination.
• KANO S.; YOKOMMATSU T.; ONO J.; HIBINO S.; SHIBUYA S., CHEM. AND PHARM. BULL., 1978, 26, NO 6, 1874-1879
  作者：KANO S.、 YOKOMMATSU T.、 ONO J.、 HIBINO S.、 SHIBUYA S.

  DOI：——

  日期：——