6-methylsulfanyl-2,4-dithioxo-1,2,3,4-tetrahydropyrimidin-5-carbonitrile | 501433-96-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-methylsulfanyl-2,4-dithioxo-1,2,3,4-tetrahydropyrimidin-5-carbonitrile
• 英文别名: 1,2,3,4-tetrahydro-6-(methylsulfanyl)-2,4-dithioxopyrimidincarbonitrile；6-methylsulfanyl-2,4-bis(sulfanylidene)-1H-pyrimidine-5-carbonitrile
• CAS: 501433-96-1
• 化学式: C₆H₅N₃S₃
• 分子量: 215.324
• InChiKey: WHAAHSZCBMMGFD-UHFFFAOYSA-N

物化性质

• 沸点：
  291.4±50.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  137
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methylsulfanyl-2,4-dithioxo-1,2,3,4-tetrahydropyrimidin-5-carbonitrile 在 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 5-amino-4-methylsulfanyl-2(morpholinocarbonylmethylsulfanyl)thieno[2,3-d]pyrimidin-6-carboxylic acid morpholide
  参考文献：
  名称：

  Synthesis and reactions of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidin‐5‐carbonitrile

  摘要：

  AbstractThe synthesis of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carbonitrile 4 is described. Compound 4 was reacted with various alkylants. The reaction with chloroacetic acid derivatives results in the formation of thieno[2,3‐d]pyrimidines 8. When methyl iodide was used 2,4,6‐tris(methylsul‐fanyl)pyrimidine‐5‐carbonitrile 5 was obtained. The substitution of the methylsulfanyl groups in compound 5 by several N‐nuclophiles leads to amino substituted pyrimidines.

  DOI：

  10.1002/jhet.5570390502
• 作为产物：
  描述：

  二硫化碳 、 丙二腈,[氨基(甲硫基)亚甲基]- 在 吡啶 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 168.0h， 以55%的产率得到6-methylsulfanyl-2,4-dithioxo-1,2,3,4-tetrahydropyrimidin-5-carbonitrile
  参考文献：
  名称：

  Synthesis and reactions of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidin‐5‐carbonitrile

  摘要：

  AbstractThe synthesis of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carbonitrile 4 is described. Compound 4 was reacted with various alkylants. The reaction with chloroacetic acid derivatives results in the formation of thieno[2,3‐d]pyrimidines 8. When methyl iodide was used 2,4,6‐tris(methylsul‐fanyl)pyrimidine‐5‐carbonitrile 5 was obtained. The substitution of the methylsulfanyl groups in compound 5 by several N‐nuclophiles leads to amino substituted pyrimidines.

  DOI：

  10.1002/jhet.5570390502

文献信息

• Selective nucleophilic replacement of the benzylsulfanyl group in 2,4-disulfanyl-substituted thieno[2,3-<i>d</i>]pyrimidin-6-carboxylic acid derivatives by secondary amines
  作者：Detlef Briel、Simon Drescher、Bodo Dobner

  DOI：10.1002/jhet.5570420514

  日期：2005.7

  Thieno[2,3-d]pyrimidines with benzylsulfanyl and allylsulfanyl group in the presence of other alkylsul-fanyl substituents react selectively under mild conditions with secondary amines under replacement of the benzyl or allyl residue whereas the other substituents remain intact. This enables the synthesis of different basic substituted derivatives with potentially biologically activity.

  在存在其他烷基硫代-芳基取代基的情况下，具有苄基硫烷基和烯丙基硫烷基的噻吩并[2,3- d ]嘧啶在温和的条件下与仲胺选择性地反应，取代了苄基或烯丙基残基，而其他取代基则保持完整。这使得能够合成具有潜在生物学活性的不同的碱性取代的衍生物。
• Selective nucleophilic substitution reactions in 2,4,6-trisulfanyl-substituted pyrimidine-5-carbonitriles by secondary amines
  作者：Simon Drescher、Daniel Ramsbeck、Bodo Dobner、Detlef Briel

  DOI：10.1002/jhet.5570440402

  日期：2007.7

  4-bis-(amidomethylsulfanyl) pyrimidine-5-carbonitriles react selective in the 2-position with various secondary cyclic amines under mild conditions. The resulting pyrimidines were finally transformed into the corresponding thieno[2,3-d]pyrimidine-6-carboxylic acid amides which afford the synthesis of selective substituted thienopyrimidines.

  高度官能化的杂环6-烷基-分别为6-芳烷基硫烷基-2,4-双-（酰胺基甲基硫烷基）嘧啶-5-腈在2-位与温和条件下的各种仲环状胺选择性反应。最后将得到的嘧啶转化为相应的噻吩并[2,3 - d ]嘧啶-6-羧酸酰胺，从而合成了选择性取代的噻吩并嘧啶。
• Synthesis and reactions of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidin‐5‐carbonitrile
  作者：Detlef Briel、Tanja Franz、Bodo Dobner

  DOI：10.1002/jhet.5570390502

  日期：2002.9

  AbstractThe synthesis of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidine‐5‐carbonitrile 4 is described. Compound 4 was reacted with various alkylants. The reaction with chloroacetic acid derivatives results in the formation of thieno[2,3‐d]pyrimidines 8. When methyl iodide was used 2,4,6‐tris(methylsul‐fanyl)pyrimidine‐5‐carbonitrile 5 was obtained. The substitution of the methylsulfanyl groups in compound 5 by several N‐nuclophiles leads to amino substituted pyrimidines.