1,3-bis(phenylsulfonyl)-4-phenyl-1,3-butadiene | 96540-11-3

• 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)-4-phenyl-1,3-butadiene
• 英文别名: 2,4-Bis(benzenesulfonyl)buta-1,3-dienylbenzene
• CAS: 96540-11-3
• 化学式: C₂₂H₁₈O₄S₂
• 分子量: 410.515
• InChiKey: ORYDCMXESDNDEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• 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)-4-phenyl-1,3-butadiene 、 苯亚甲基甲胺 以 二氯甲烷 为溶剂， 反应 24.0h， 以82%的产率得到3,5-bis(phenylsulfonyl)-2,6-diphenyl-1-methyl-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 哌啶 、 溶剂黄146 作用下， 以 甲醇 、 苯 为溶剂， 反应 4.58h， 生成 1,3-bis(phenylsulfonyl)-4-phenyl-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

• Phosphine-catalyzed sequential annulation domino reaction: rapid construction of bicyclo[4.1.0]heptene skeletons
  作者：Jie Zheng、You Huang、Zhengming Li

  DOI：10.1039/c4cc01097c

  日期：——

  A convenient and efficient phosphine-catalyzed sequential annulation domino reaction between dienic sulfones and MBH carbonates has been developed. In the presence of 20 mol% of tris(4-fluorophenyl)phosphine, functionalized bicyclo[4.1.0]heptenes were prepared in excellent yields and stereoselectivities under mild conditions.

  开发了一种方便高效的膦催化顺序环化多米诺反应，适用于二烯磺酸盐和MBH碳酸酯。在20%摩尔的三（4-氟苯基）膦存在下，在温和条件下合成了功能化的双环[4.1.0]庚烯，产率和立体选择性均优良。
• Phosphine-Catalyzed Domino Reaction: An Efficient Method for the Synthesis of Bicyclo[3.2.0]heptenes Skeleton
  作者：Jie Zheng、You Huang、Zhengming Li

  DOI：10.1021/ol402799w

  日期：2013.11.15

  Dienic sulfones and γ-CH3 allenoates can be converted into bicyclo[3.2.0]heptene derivatives in moderate to good yield using trimethylphosphine as the catalyst under mild conditions.

  二烯砜和γ-CH 3层的联烯酸酯可以使用三甲基膦作为在温和条件下的催化剂转化为二环[3.2.0]庚烯衍生物在中度至良好的产率。
• Nazarov Reagent: New Role for the [4+2] Domino Benzannulation Reaction to Construct Polysubstituted Benzenes
  作者：Meijia Chang、You Huang

  DOI：10.1002/asia.201900590

  日期：2019.8

  A new role for the Nazarov reagent was revealed in the [4+2] benzannulation reaction, and delivered a series of polyfunctional benzenes in high yields under mild conditions. This metal‐free process not only expanded the application of the Nazarov reagent in organic synthesis, but also provided a new, efficient way to construct polyfunctional benzenes.

  纳扎罗夫试剂的新作用在[4 + 2]苄环反应中得到揭示，并在温和条件下以高收率递送了一系列多官能苯。这种无金属工艺不仅扩大了纳扎罗夫试剂在有机合成中的应用，而且为构建多官能苯提供了一种新的有效途径。
• Phosphine-Catalyzed Domino Benzannulation: An Efficient Method to Construct Biaryl Skeletons
  作者：Jie Zheng、You Huang、Zhengming Li

  DOI：10.1021/ol4022904

  日期：2013.10.4

  The first phosphine-catalyzed domino benzannulation reaction to prepare a variety of functionalized biaryls from allenoates and dienic sulfones is developed.