(Z)-4-(bis(ethylthio)methylene)-5-((E)-3-(bis(ethylthio)methylene)-2,6-bis(4-chlorophenyl)-4-oxohex-5-enylidene)dihydrofuran-2,3-dione | 1170697-88-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-4-(bis(ethylthio)methylene)-5-((E)-3-(bis(ethylthio)methylene)-2,6-bis(4-chlorophenyl)-4-oxohex-5-enylidene)dihydrofuran-2,3-dione
• 英文别名: (5Z)-4-[bis(ethylsulfanyl)methylidene]-5-[(E)-3-[bis(ethylsulfanyl)methylidene]-2,6-bis(4-chlorophenyl)-4-oxohex-5-enylidene]oxolane-2,3-dione
• CAS: 1170697-88-7
• 化学式: C₃₂H₃₂Cl₂O₄S₄
• 分子量: 679.774
• InChiKey: LJCBGMGKEKTKDN-YPYFWSIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  162
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (Z)-4-(bis(ethylthio)methylene)-5-((E)-3-(bis(ethylthio)methylene)-2,6-bis(4-chlorophenyl)-4-oxohex-5-enylidene)dihydrofuran-2,3-dione 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 7.0h， 生成 S-ethyl 2-(7-(bis(ethylthio)methylene)-6,9-bis(4-chlorophenyl)-2-(ethylthio)-4,8-dioxobicyclo[3.3.1]non-2-en-3-yl)-2-oxoethanethioate 、 S-ethyl 2-(7-(bis(ethylthio)methylene)-6,9-bis(4-chlorophenyl)-2-(ethylthio)-4,8-dioxobicyclo[3.3.1]non-2-en-3-yl)-2-oxoethanethioate
  参考文献：
  名称：

  A Synthetic Strategy for Polyfunctionalized Bicyclo[3.3.1]nonanes Based on a Tandem Three-Component [3 + 2] Cycloaddition of α-Cinnamoyl Ketene-S,S-acetals with Oxalyl Chloride

  摘要：

  A simple and highly efficient three-component reaction of the readily available alpha-cinnamoyl ketene-S,S-acetals 1 with oxalyl chloride has been developed and the corresponding gamma-alkylidenebutenolides 2 were obtained stereospecifically in excellent yields under very mild conditions. On the basis of this reaction, a series of highly functionalized bicyclo[3.3.1]nonanes 3 were constructed in good to high yields in an atom-economic manner with good diastereoselectivity via a BF(3)center dot OEt(2)-mediated novel tandem double cyclization of gamma-alkylidenebutenolides 2 under very mild conditions.

  DOI：

  10.1021/jo900764s
• 作为产物：
  描述：

  草酰氯 、 5-(4-chlorophenyl)-1,1-bis(ethylsulfanyl)penta-1,4-dien-3-one 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以96%的产率得到(Z)-4-(bis(ethylthio)methylene)-5-((E)-3-(bis(ethylthio)methylene)-2,6-bis(4-chlorophenyl)-4-oxohex-5-enylidene)dihydrofuran-2,3-dione
  参考文献：
  名称：

  A Synthetic Strategy for Polyfunctionalized Bicyclo[3.3.1]nonanes Based on a Tandem Three-Component [3 + 2] Cycloaddition of α-Cinnamoyl Ketene-S,S-acetals with Oxalyl Chloride

  摘要：

  A simple and highly efficient three-component reaction of the readily available alpha-cinnamoyl ketene-S,S-acetals 1 with oxalyl chloride has been developed and the corresponding gamma-alkylidenebutenolides 2 were obtained stereospecifically in excellent yields under very mild conditions. On the basis of this reaction, a series of highly functionalized bicyclo[3.3.1]nonanes 3 were constructed in good to high yields in an atom-economic manner with good diastereoselectivity via a BF(3)center dot OEt(2)-mediated novel tandem double cyclization of gamma-alkylidenebutenolides 2 under very mild conditions.

  DOI：

  10.1021/jo900764s