1-(Furan-2-yl)-3-methylsulfanyl-3-thiophen-2-ylprop-2-en-1-one | 1416249-61-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(Furan-2-yl)-3-methylsulfanyl-3-thiophen-2-ylprop-2-en-1-one
• 英文别名: 1-(furan-2-yl)-3-methylsulfanyl-3-thiophen-2-ylprop-2-en-1-one
• CAS: 1416249-61-0
• 化学式: C₁₂H₁₀O₂S₂
• 分子量: 250.342
• InChiKey: WTMCNVXJSYJBIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  83.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二碘甲烷 、 1-(Furan-2-yl)-3-methylsulfanyl-3-thiophen-2-ylprop-2-en-1-one 在 zinc-copper couple 、 碘 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 1.0h， 以52%的产率得到2-(2,2'-bithiophen-4-yl)furan
  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-乙酰基呋喃 、 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 1-(Furan-2-yl)-3-methylsulfanyl-3-thiophen-2-ylprop-2-en-1-one
  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

文献信息

• Attempted Simmon–Smith reaction on β-alkylthio-α,β-unsaturated ketones: a regiospecific synthesis of 2,4-disubstituted thiophenes
  作者：Toreshettahally R. Swaroop、Rangaswamy Roopashree、Hiriyakkanavar Ila、Kanchugarakoppal S. Rangappa

  DOI：10.1016/j.tetlet.2012.10.110

  日期：2013.1

  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.