1,3-dithiolan-2-ylidenecyanoacetic acid | 2080-63-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 1,3-dithiolan-2-ylidenecyanoacetic acid
• 英文别名: 2-<1.3>Dithiolan-2-yl-malonsaeure-mononitril；cyano-[1,3]dithiolan-2-ylidene-acetic acid；Quobcvisqapsfg-uhfffaoysa-；2-cyano-2-(1,3-dithiolan-2-ylidene)acetic acid
• CAS: 2080-63-9
• 化学式: C₆H₅NO₂S₂
• 分子量: 187.243
• InChiKey: QUOBCVISQAPSFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,2-二溴乙烷 、 以 二甲基亚砜 为溶剂， 反应 2.0h， 以44%的产率得到1,3-dithiolan-2-ylidenecyanoacetic acid
  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

表征谱图