1,3-bis(phenylsulfonyl)-1,3-butadiene | 126281-42-3

• 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: 1,3-bis(phenylsulfonyl)-1,3-butadiene
• 英文别名: 1,1'-(Buta-1,3-diene-1,3-diyldisulfonyl)dibenzene；3-(benzenesulfonyl)buta-1,3-dienylsulfonylbenzene
• CAS: 126281-42-3
• 化学式: C₁₆H₁₄O₄S₂
• 分子量: 334.417
• InChiKey: UQOZZLXJCJIYQL-UHFFFAOYSA-N

物化性质

• 沸点：
  568.8±46.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-bis(phenylsulfonyl)-1,3-butadiene 、 苯亚甲基甲胺 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到3,5-bis(phenylsulfonyl)-1-methyl-2-phenyl-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  Formation of polysubstituted 1,2,5,6-tetrahydropyridines from the 4+2 cycloaddition reaction of bis(phenylsulfonyl)butadienes with aryl imines

  摘要：

  The reaction of 2,3-bis(phenylsulfonyl)-1,3-butadiene with aryl imines affords N-alkyl-3,5-bis(phenylsulfonyl)-1,2,5,6-tetrahydropyridines in high yield. The formation of the rearranged cycloadducts proceeds by a mechanism that involves addition of benzenesulfinate anion onto the terminal pi-bond of the activated diene. The resulting carbanion undergoes proton transfer followed by aryl sulfinate ejection to give 1,3-bis(phenylsulfonyl)-1,3-butadiene as a transient intermediate. This reactive diene undergoes a rapid 4 + 2 cycloaddition followed by a subsequent hydrogen 1,3-shift. Support for the proposed mechanism is provided by the observation that a mixed cycloadduct is obtained from the reaction of a 1:1 mixture of 2,3-bis(phenylsulfonyl)- and 2,3-bis[(o-nitrophenyl)sulfonyl]butadiene with N-benzylidenemethylamine. An additional piece of supporting data for the proposed mechanism is the much shorter reaction time necessary for the reaction to go to completion when a small amount of sodium benzenesulfinate is added to the reaction mixture. 1,3-Bis(phenylsulfonyl)butadiene was independently synthesized by two different routes. This diene was found to rapidly react with a variety of imines to give the same cycloadducts as those derived from the 2,3-isomer. The reaction of several 4-substituted 1,3-bis(phenylsulfonyl)butadienes with aryl imines was found to give related 4 + 2 cycloadducts.

  DOI：

  10.1021/jo00008a026
• 作为产物：
  描述：

  (3-bromo-propenyl)-phenyl sulfone 在 正丁基锂 、 三溴化磷 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.25h， 生成 1,3-bis(phenylsulfonyl)-1,3-butadiene
  参考文献：
  名称：

  Formation of polysubstituted 1,2,5,6-tetrahydropyridines from the 4+2 cycloaddition reaction of bis(phenylsulfonyl)butadienes with aryl imines

  摘要：

  The reaction of 2,3-bis(phenylsulfonyl)-1,3-butadiene with aryl imines affords N-alkyl-3,5-bis(phenylsulfonyl)-1,2,5,6-tetrahydropyridines in high yield. The formation of the rearranged cycloadducts proceeds by a mechanism that involves addition of benzenesulfinate anion onto the terminal pi-bond of the activated diene. The resulting carbanion undergoes proton transfer followed by aryl sulfinate ejection to give 1,3-bis(phenylsulfonyl)-1,3-butadiene as a transient intermediate. This reactive diene undergoes a rapid 4 + 2 cycloaddition followed by a subsequent hydrogen 1,3-shift. Support for the proposed mechanism is provided by the observation that a mixed cycloadduct is obtained from the reaction of a 1:1 mixture of 2,3-bis(phenylsulfonyl)- and 2,3-bis[(o-nitrophenyl)sulfonyl]butadiene with N-benzylidenemethylamine. An additional piece of supporting data for the proposed mechanism is the much shorter reaction time necessary for the reaction to go to completion when a small amount of sodium benzenesulfinate is added to the reaction mixture. 1,3-Bis(phenylsulfonyl)butadiene was independently synthesized by two different routes. This diene was found to rapidly react with a variety of imines to give the same cycloadducts as those derived from the 2,3-isomer. The reaction of several 4-substituted 1,3-bis(phenylsulfonyl)butadienes with aryl imines was found to give related 4 + 2 cycloadducts.

  DOI：

  10.1021/jo00008a026

文献信息

• Formation of polysubstituted 1,2,5,6-tetrahydropyridines from the 4+2 cycloaddition reaction of bis(phenylsulfonyl)butadienes with aryl imines
  作者：Albert Padwa、Yves Gareau、Brian Harrison、Bryan H. Norman

  DOI：10.1021/jo00008a026

  日期：1991.4

  The reaction of 2,3-bis(phenylsulfonyl)-1,3-butadiene with aryl imines affords N-alkyl-3,5-bis(phenylsulfonyl)-1,2,5,6-tetrahydropyridines in high yield. The formation of the rearranged cycloadducts proceeds by a mechanism that involves addition of benzenesulfinate anion onto the terminal pi-bond of the activated diene. The resulting carbanion undergoes proton transfer followed by aryl sulfinate ejection to give 1,3-bis(phenylsulfonyl)-1,3-butadiene as a transient intermediate. This reactive diene undergoes a rapid 4 + 2 cycloaddition followed by a subsequent hydrogen 1,3-shift. Support for the proposed mechanism is provided by the observation that a mixed cycloadduct is obtained from the reaction of a 1:1 mixture of 2,3-bis(phenylsulfonyl)- and 2,3-bis[(o-nitrophenyl)sulfonyl]butadiene with N-benzylidenemethylamine. An additional piece of supporting data for the proposed mechanism is the much shorter reaction time necessary for the reaction to go to completion when a small amount of sodium benzenesulfinate is added to the reaction mixture. 1,3-Bis(phenylsulfonyl)butadiene was independently synthesized by two different routes. This diene was found to rapidly react with a variety of imines to give the same cycloadducts as those derived from the 2,3-isomer. The reaction of several 4-substituted 1,3-bis(phenylsulfonyl)butadienes with aryl imines was found to give related 4 + 2 cycloadducts.