(E)-2-(bis(benzylthio)methylene)-1,4-diphenylbut-3-en-1-one | 1293365-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-(bis(benzylthio)methylene)-1,4-diphenylbut-3-en-1-one
• 英文别名: (E)-2-[bis(benzylsulfanyl)methylidene]-1,4-diphenylbut-3-en-1-one
• CAS: 1293365-21-5
• 化学式: C₃₁H₂₆OS₂
• 分子量: 478.679
• InChiKey: ICKKLUWMWNSHGU-QURGRASLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(bis(benzylthio)methylene)-1,4-diphenylbut-3-en-1-one 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以60%的产率得到(2-(benzylthio)-5-phenylfuran-3-yl)(phenyl)methanone
  参考文献：
  名称：

  Synthesis of 2,3,5-trisubstituted furans from α-formylaroylketene dithioacetals

  摘要：

  A new strategy for the synthesis of 2,3,5-trisbustituted furans from alpha-formylketene dithioacetals is described. The protocol involves a facile conversion of alpha-formylketene dithioacetals to vinylketene dithioacetals via Wittig reaction and subsequent N-bromosuccinimide-mediated cyclization to 2,3,5-trisbustituted furans. Further conversion of the 2-thioalkylfurans thus obtained to 2-aminofurans shows the potential synthetic utility of this new approach. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.128
• 作为产物：
  描述：

  苄基三苯基氯化膦 、 2-benzoyl-3,3-bis(benzylsulfanyl)acrylaldehyde 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.08h， 以78%的产率得到(E)-2-(bis(benzylthio)methylene)-1,4-diphenylbut-3-en-1-one
  参考文献：
  名称：

  Synthesis of 2,3,5-trisubstituted furans from α-formylaroylketene dithioacetals

  摘要：

  A new strategy for the synthesis of 2,3,5-trisbustituted furans from alpha-formylketene dithioacetals is described. The protocol involves a facile conversion of alpha-formylketene dithioacetals to vinylketene dithioacetals via Wittig reaction and subsequent N-bromosuccinimide-mediated cyclization to 2,3,5-trisbustituted furans. Further conversion of the 2-thioalkylfurans thus obtained to 2-aminofurans shows the potential synthetic utility of this new approach. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.128

文献信息

• Synthesis of 2,3,5-trisubstituted furans from α-formylaroylketene dithioacetals
  作者：K.A. Sasikala、K.A. Kalesh、E.R. Anabha、P. Madhavan Pillai、C.V. Asokan、K.S. Devaky

  DOI：10.1016/j.tetlet.2011.01.128

  日期：2011.4

  A new strategy for the synthesis of 2,3,5-trisbustituted furans from alpha-formylketene dithioacetals is described. The protocol involves a facile conversion of alpha-formylketene dithioacetals to vinylketene dithioacetals via Wittig reaction and subsequent N-bromosuccinimide-mediated cyclization to 2,3,5-trisbustituted furans. Further conversion of the 2-thioalkylfurans thus obtained to 2-aminofurans shows the potential synthetic utility of this new approach. (c) 2011 Elsevier Ltd. All rights reserved.