2-(N-methylanilino)-2-phenylthioacetonitrile | 132431-15-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(N-methylanilino)-2-phenylthioacetonitrile
• 英文别名: 2-(N-methylanilino)-2-phenylsulfanylacetonitrile
• CAS: 132431-15-3
• 化学式: C₁₅H₁₄N₂S
• 分子量: 254.356
• InChiKey: QZGODRDDRUHWRH-UHFFFAOYSA-N

物化性质

• 沸点：
  381.2±37.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(N-methylanilino)-2-phenylthioacetonitrile 在 六甲基磷酰三胺 、 偶氮二异丁腈 、 氧气 、 三正丁基氢锡 、 lithium diisopropyl amide 作用下， 以 环己烷 、 苯 为溶剂， 反应 14.0h， 生成 9-甲基-2,3,4,9-四氢-1H-咔唑-1-酮
  参考文献：
  名称：

  Nucleophilic-type radical cyclizations of indoles: conversion of 2-cyano 3-substituted indoles to spiro-annelated indolines and tetrahydrocarbazolones

  摘要：

  Oxidative photocyclizations of appropriate 2-anilino alkenenitriles (6) afforded a series of indole-2-carbonitriles (7) having bromoalkyl substituents at the C-3 positions. Upon treatment with Bu3SnH, these indolecarbonitriles underwent intramolecular cyclizations either by attack at the C-3 positions of the indole rings to give the spiro-annelated indolinecarbonitriles or by attack at the cyano group to give carbazolone derivatives.

  DOI：

  10.1021/jo00063a032
• 作为产物：
  描述：

  N-甲基甲酰苯胺 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 四甲基二硅氮烷 、 lithium diisopropyl amide 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 2-(N-methylanilino)-2-phenylthioacetonitrile
  参考文献：
  名称：

  铁催化还原斯特雷克反应

  摘要：

  斯特雷克反应被广泛应用于由醛，胺和氰化物合成氨基酸。在本文中，我们报道了FeI 2催化的甲酰胺而不是醛的还原斯特雷克型反应生成氨基乙腈。通过CN甲醇胺中间体的具有挑战性的拍摄-达到了通过铁催化。与使用Ir或Rh催化剂相比，此方法可提供更好的产率。这种方法的应用能力通过以下方式得到证明：1）通过氨基乙腈从一氧化碳（CO 2）中一锅构建（13 C标记的）复杂分子，以及2） 由醛方便地生产同系羧酸。

  DOI：

  10.1016/j.jcat.2021.01.003

文献信息

• Yang, Chau-Chen; Fang, Jim-Min, Journal of the Chemical Society. Perkin transactions I, 1992, # 22, p. 3085 - 3094
  作者：Yang, Chau-Chen、Fang, Jim-Min

  DOI：——

  日期：——
• 2-(N-Methylanilino)-2-phenylthioacetonitrile: a useful reagent for preparation of conjugated α-amino alkenenitriles via tandem alkylation and dehydrosulphenylation
  作者：Jim-Min Fang、Chin-Cheng Chen

  DOI：10.1039/p19900003365

  日期：——

  Alkylation of the anion of 2-(N-methylanilino)-2-phenylthioacetonitrile 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated alpha-aminoalkenenitriles of 2E-configuration. Counterattack by bromide and benzenethiolate ions was observed in the prolonged reactions of 1 with 1,4-dibromobut-2-ene and 3-bromo-1-(trimethylsilyl)prop-1-yne.
• 2-(N-methylanilino)-2-phenylsulfanylacetonitrile, a reagent tested for electrophilic, nucleophilic and radical reactions
  作者：Chih-Cheng Chen、Same-Ting Chen、Tsung-Hsun Chuang、Jim-Min Fang

  DOI：10.1039/p19940002217

  日期：——

  2-(N-Methylanilino) -2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide. Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated alpha-aminoalkenenitriles of 2E-configuration. Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates. Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by Cul or Lewis acids to give varied alpha-amino nitriles. The 4-oxo-2-amino nitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung. When 1 was treated with tributylstannane, the corresponding amino nitrile alpha-radical was formed and the self-coupling product was isolated.
• CHUANG, TSUNG-HSUN;YANG, CHAU-CHEN;CHANG, CHIH-JUNG;FANG, JIM-MIN, SYNLETT.,(1990) N2, C. 733-734
  作者：CHUANG, TSUNG-HSUN、YANG, CHAU-CHEN、CHANG, CHIH-JUNG、FANG, JIM-MIN

  DOI：——

  日期：——
• FANG, JIM-MIN;CHEN, CHIH-CHENG, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N2, C. 3365-3367
  作者：FANG, JIM-MIN、CHEN, CHIH-CHENG

  DOI：——

  日期：——