3-cyano-4,5-dihydro-5-methyl-2-thiopheneacetonitrile | 1222510-54-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 3-cyano-4,5-dihydro-5-methyl-2-thiopheneacetonitrile
• CAS: 1222510-54-4
• 化学式: C₈H₈N₂S
• 分子量: 164.231
• InChiKey: DQHYIDBODMIHJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  47.58
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-cyano-4,5-dihydro-5-methyl-2-thiopheneacetonitrile 在 sulfur 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以71%的产率得到4-amino-2,3-dihydro-2-methyl-thieno[3,4-b]thiophene-6-carbonitrile
  参考文献：
  名称：

  Synthesis of Fused Thiopyranthione and Thiophene Derivatives from 4,5-Dihydro-3-thiophene(and -3-furan)carbonitriles Having an Active Methylene Group at C-2 Position

  摘要：

  A versatile strategy is described for the synthesis of new fused thiopyranthione and thiophene derivatives. The reaction of heterocyclic alpha,beta-unsaturated nitrites 3a-c, 4a-d, 5a-c, and 6a-d, which were prepared from tetrahydro-2-oxo-3-thiophene- and -3-furan-carbonitriles 1a-c and/or 2a-d and alkylidene phosphoranes such as (triphenylphosphoranylidene)acetonitrile and methyl (triphenylphosphoranylidene)acetate through Wittig reaction, with carbon disulfide in the presence of sodium hydride in THF gave the corresponding 6-thioxothieno[3,2-c]thiopyran and 6-thioxothiopyrano[4,3-b]furan derivatives 7a-c, 8a-d, 9a-c, and 10a-d. On the other hand, treatment of compounds 3a-c, 5a-c, and 6a-d with sulfur powder in the presence of triethylamine in methanol caused Gewald reaction to provide the corresponding thieno[3,4-b]thiophene and -furan derivatives 11a-c, 12a-c, and 13a-d.

  DOI：

  10.3987/com-09-11894
• 作为产物：
  描述：

  tetrahydro-5-methyl-2-oxo-3-thiophenecarbonitrile 、 (三苯基膦)乙腈 以 甲苯 为溶剂， 反应 8.0h， 以98%的产率得到3-cyano-4,5-dihydro-5-methyl-2-thiopheneacetonitrile
  参考文献：
  名称：

  Synthesis of Fused Thiopyranthione and Thiophene Derivatives from 4,5-Dihydro-3-thiophene(and -3-furan)carbonitriles Having an Active Methylene Group at C-2 Position

  摘要：

  A versatile strategy is described for the synthesis of new fused thiopyranthione and thiophene derivatives. The reaction of heterocyclic alpha,beta-unsaturated nitrites 3a-c, 4a-d, 5a-c, and 6a-d, which were prepared from tetrahydro-2-oxo-3-thiophene- and -3-furan-carbonitriles 1a-c and/or 2a-d and alkylidene phosphoranes such as (triphenylphosphoranylidene)acetonitrile and methyl (triphenylphosphoranylidene)acetate through Wittig reaction, with carbon disulfide in the presence of sodium hydride in THF gave the corresponding 6-thioxothieno[3,2-c]thiopyran and 6-thioxothiopyrano[4,3-b]furan derivatives 7a-c, 8a-d, 9a-c, and 10a-d. On the other hand, treatment of compounds 3a-c, 5a-c, and 6a-d with sulfur powder in the presence of triethylamine in methanol caused Gewald reaction to provide the corresponding thieno[3,4-b]thiophene and -furan derivatives 11a-c, 12a-c, and 13a-d.

  DOI：

  10.3987/com-09-11894