(E)-3-benzylamino-3-(methylthio)propenonitrile | 113966-69-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-3-benzylamino-3-(methylthio)propenonitrile
• 英文别名: (E)-3-(Benzylamino)-3-(methylthio)acrylonitrile；3-Benzylamino-3-methylsulfanyl-acrylonitrile；(E)-3-(benzylamino)-3-methylsulfanylprop-2-enenitrile
• CAS: 113966-69-1
• 化学式: C₁₁H₁₂N₂S
• 分子量: 204.296
• InChiKey: IKKAPSHWVXIXPR-YRNVUSSQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄胺 、 2-cyano-3,3-bis(methylsulfanyl)prop-2-enoic acid 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 96.0h， 以3%的产率得到β,β-Dibenzylamino-acrylnitril
  参考文献：
  名称：

  Sodium 2-Cyanoethylene-1,1-dithiolate Tetrahydrate: a Stable Salt of Cyanodithioacetic Acid. A New Preparative Route to 2-Cyanoketene S,S-, S,N- and N,N-Acetals.

  摘要：

  2-Cyanoethylene-1,1-dithiolate, the dianion of cyanodithioacetic acid, is prepared from ethyl cyanoacetate by condensation with carbon disulfide followed by hydrolysis and decarboxylation with sodium hydroxide. The anion has been isolated and characterized as a stable, tetrahydrated sodium salt (2) and alkylated to give 3,3-bis(alkylthio)propenonitriles (3) in excellent yields. Alkylation of an intermediate, unstable trianion of 2-cyano-1,1-dithiomalonic acid (4) gives 3,3-bis(methylthio)-2-cyanopropenic acid (6a) which on treatment with mono- and di-alkylamines undergoes consecutive substitution and decarboxylation to 3-amino-3-(methylthio)propenonitriles (7). The application of 1,2-diamines or 2-aminoethanethiol leads to cyclized products, (imidazolidin-2-ylidene) acetonitriles(9) and (1,3-thiazolidin-2-ylidene)acetonitrile (10), respectively.

  DOI：

  10.3891/acta.chem.scand.50-0432

文献信息

• Synthesis of<i>N</i>-Substituted 5-Hydroxyindoles
  作者：Masataka Yokoyama、Satoshi Watanabe、Hidekatsu Hatanaka

  DOI：10.1055/s-1987-28100

  日期：——

  α-Methylthio-β-cyanoenamines are found to be useful starting compounds for the synthesis of N-substituted 5-hydroxyindoles. In connection with the preparation of the starting compounds, a novel decarboxyamidation is presented.

  δ-甲硫基-δ-氰胺是合成 N-取代的 5-羟基吲哚的有用起始化合物。在制备起始化合物的过程中，介绍了一种新型的脱羧基酰胺化反应。

表征谱图