4-(1,1-Dioxo-4-phenylsulfanyl-2,5-dihydrothiophen-2-yl)butanal | 197862-46-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(1,1-Dioxo-4-phenylsulfanyl-2,5-dihydrothiophen-2-yl)butanal
• CAS: 197862-46-7
• 化学式: C₁₄H₁₆O₃S₂
• 分子量: 296.411
• InChiKey: LSOAYMCINFJFEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  84.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(1,1-Dioxo-4-phenylsulfanyl-2,5-dihydrothiophen-2-yl)butanal 在 对苯二酚 、 sodium formate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.25h， 生成 (4aS,8aS)-7-Phenylsulfanyl-3,4,4a,5,8,8a-hexahydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Intramolecular Diels-Alder Reactions of Thio-Substituted Dienes with Enones

  摘要：

  AbstractThio‐substituted dienes bearing an enone moiety were readily prepared from 3‐sulfolenes, and their intramolecular Diels‐Alder (IMDA) reactions were studied. Octahydronaphthalenones were produced in good yield with high stereoselectivity. Hexahydroindenones were also obtained, but the stereoselectivity was lower.

  DOI：

  10.1002/jccs.199700055
• 作为产物：
  描述：

  3-thiophenyl-3-sulfolene 在 六甲基磷酰三胺 、 sodium hydroxide 、 9-borabicyclo[3.3.1]nonane dimer 、 正丁基锂 、 双氧水 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-(1,1-Dioxo-4-phenylsulfanyl-2,5-dihydrothiophen-2-yl)butanal
  参考文献：
  名称：

  硝酮与硫取代的二烯的分子内环加成反应及其合成应用

  摘要：

  从3-环丁烯前体方便地制备了一系列硫取代的二烯基硝基酮。分子内的1，3-偶极环加成反应得到稠合的双环异恶唑烷。已经研究了这些反应的区域和立体化学结果以及合成应用。

  DOI：

  10.1016/s0040-4039(97)01037-x

文献信息

• Intramolecular cycloaddition of nitrones with sulfur-substituted dienes and its synthetic applications
  作者：Shang-Shing P. Chou、Yu-Ju Yu

  DOI：10.1016/s0040-4039(97)01037-x

  日期：1997.7

  A series of sulfur-substituted dienyl nitrones were conviently prepared from the 3-sulfolene precursors. Intramolecular 1,3-dipolar cycloaddition reactions gave the fused bicyclic isoxazolidines. The regio- and stereochemical outcome of these reactions as well as the synthetic applications have been explored.

  从3-环丁烯前体方便地制备了一系列硫取代的二烯基硝基酮。分子内的1，3-偶极环加成反应得到稠合的双环异恶唑烷。已经研究了这些反应的区域和立体化学结果以及合成应用。
• Intramolecular Cycloaddition of Nitrones and Nitrile Oxides with Sulfur-Substituted Dienes and Its Synthetic Applications
  作者：Shang-Shing P. Chou、Yu-Ju Yu

  DOI：10.1002/jccs.199800028

  日期：1998.2

  AbstractA series of sulfur‐substituted dienyl nitrones and oximes were conveniently prepared from the 3‐sulfolene precursors. Regiospecific intramolecular 1,3‐dipolar cycloadditions of nitrones and nitrile oxides with sulfur‐substituted dienes have been efficiently carried out from the suitable 3‐sulfolene precursors. The stereochemistry of the cycloaddition of nitrones depends on the structure of the substituent (sulfide or sulfone) on the diene as well as on the chain length connecting the diene and nitrone. The fused bicyclic products obtained from these reactions have been converted to some interesting heterocyclic compounds which have the useful structure of vinyl sulfide or sulfone.
• Intramolecular Diels-Alder Reactions of Thio-Substituted Dienes with Enones
  作者：Shang-Shing P. Chou、Yu-Ju Yu

  DOI：10.1002/jccs.199700055

  日期：1997.8

  AbstractThio‐substituted dienes bearing an enone moiety were readily prepared from 3‐sulfolenes, and their intramolecular Diels‐Alder (IMDA) reactions were studied. Octahydronaphthalenones were produced in good yield with high stereoselectivity. Hexahydroindenones were also obtained, but the stereoselectivity was lower.