| 1416249-60-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1416249-60-9
• 化学式: C₁₂H₁₀OS₃
• 分子量: 266.409
• InChiKey: RYDGYCCDCYFTBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二碘甲烷 、 在 zinc-copper couple 、 碘 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 1.0h， 以57%的产率得到2,4-二噻吩-2-基噻吩
  参考文献：
  名称：

  Attempted Simmon–Smith reaction on β-alkylthio-α,β-unsaturated ketones: a regiospecific synthesis of 2,4-disubstituted thiophenes

  摘要：

  A new regiospecific route to 2,4-disubstituted thiophenes has been developed through Simmon-Smith reaction on beta-methylthio-alpha,beta-unsaturated ketones. Extension of the reaction to beta-ethylibenzylthio-alpha,beta-unsaturated ketones also gave the corresponding 2,4-disubstituted thiophenes in a regiospecific manner. A probable mechanism involving a carbenoid methylene insertion to divalent sulfur followed by intramolecular aldol condensation has been suggested.[GRAPHICS](C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.110
• 作为产物：
  描述：

  2-乙酰基噻吩 、 thiophene-2-carbodithioic acid methyl ester 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Attempted Simmon–Smith reaction on β-alkylthio-α,β-unsaturated ketones: a regiospecific synthesis of 2,4-disubstituted thiophenes

  摘要：

  A new regiospecific route to 2,4-disubstituted thiophenes has been developed through Simmon-Smith reaction on beta-methylthio-alpha,beta-unsaturated ketones. Extension of the reaction to beta-ethylibenzylthio-alpha,beta-unsaturated ketones also gave the corresponding 2,4-disubstituted thiophenes in a regiospecific manner. A probable mechanism involving a carbenoid methylene insertion to divalent sulfur followed by intramolecular aldol condensation has been suggested.[GRAPHICS](C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.110