1,3-bis(phenylsulfonyl)-1-propene | 38513-20-1

• 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-propene
• 英文别名: 1,3-bis-(phenylsulfonyl)propene；1,3-bis(phenylsulfonyl)propene；1,3-Bis-benzolsulfonyl-propen-(1)；1,3-Diphenylsulfonylpropen；1,3-Bisphenylsulfonylpropene；3-(benzenesulfonyl)prop-2-enylsulfonylbenzene
• CAS: 38513-20-1
• 化学式: C₁₅H₁₄O₄S₂
• 分子量: 322.406
• InChiKey: RSTGVZDDFHPCLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-propene 在 正丁基锂 、 三溴化磷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 13.67h， 生成 1-benzyl-3,5-bis(phenylsulfonyl)-2-ethyl-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：

  1,3-bis(phenylthio)-1-propene 在 双氧水 作用下， 以 溶剂黄146 为溶剂， 生成 1,3-bis(phenylsulfonyl)-1-propene
  参考文献：
  名称：

  Reactions of 3,3-dichloropropene and of crotonaldehyde with alkane (or arene) thiols

  摘要：

  DOI：

  10.1007/bf00908029

文献信息

• Secondary amine-catalyzed [3 + 3] benzannulation to access polysubstituted benzenes through iminium activation
  作者：Lin Jiang、Hang Li、Jiang-Feng Zhou、Ming-Wei Yuan、Hong-Li Li、Yong-Ming Chuan、Ming-Long Yuan

  DOI：10.1080/00397911.2017.1402351

  日期：2018.2.1

  ABSTRACT An organocatalytic [3 + 3] benzannulation to access polysubstituted benzenes from readily available α,β-unsaturated aldehydes and 1,3-bis(phenylsulfonyl)propene or 4-sulfonylcrotonates is described. The key reaction step is considered to be the iminium activation of enals by a secondary aminocatalyst. This organocatalytic protocol avoids the traditional strategy which is always with the aid

  摘要描述了一种有机催化 [3 + 3] 苯并环化，以从容易获得的 α,β-不饱和醛和 1,3-双（苯磺酰基）丙烯或 4-磺酰基巴豆酸酯中获得多取代苯。关键反应步骤被认为是仲氨基催化剂对烯醛的亚胺活化。这种有机催化方案避免了总是借助过渡金属或化学计量量的强碱的传统策略，并允许以高到极好的收率（74-96%）合成三取代苯。图形概要
• Facile synthesis of biarylmethanes and tetrasubstituted arenes <i>via</i> a base-mediated [3 + 3] benzannulation reaction of Morita–Baylis–Hillman adducts and unsaturated sulfones
  作者：Deepak Yadav、Sunil K. Sharma、Rajeev S. Menon

  DOI：10.1039/c9ob00214f

  日期：——

  A facile DBU-mediated [3 + 3] benzannulation reaction of 1,3-bis-sulfonyl propenes and Morita–Baylis–Hillman (MBH) bromides is described. The benzannulation reaction afforded bis-sulfonyl biarylmethanes/arenes with complete regioselectivity. The products may be converted readily into corresponding benzophenones via site-selective benzylic oxidation.

  描述了一种简单的DBU介导的1，3-双磺酰基丙烯与Morita-Baylis-Hillman（MBH）溴化物的[3 + 3]苯并环反应。苯并环化反应提供具有完全区域选择性的双磺酰基联芳基甲烷/芳烃。产物可以通过位点选择性苄基氧化容易地转化为相应的二苯甲酮。
• Asymmetric Organocatalytic 1,6-Conjugate Addition of Aldehydes to Dienic Sulfones
  作者：John J. Murphy、Adrien Quintard、Patrick McArdle、Alexandre Alexakis、John C. Stephens

  DOI：10.1002/anie.201100804

  日期：2011.5.23

  An unprecedented 1,6‐enamine conjugate addition exploiting the charge delocalization in 1,3‐bis(sulfonyl) butadienes has been developed. By appropriately designing a Michael acceptor, unique reactivities were obtained for the formation of highly valuable dienes containing two versatile vinyl sulfones (see scheme, TMS=trimethylsilyl).

  利用1,3-双（磺酰基）丁二烯中电荷的离域作用，开发了前所未有的1,6-烯胺共轭物。通过适当设计迈克尔受体，获得了独特的反应性，可用于形成含有两种通用乙烯基砜的高价值二烯（参见方案，TMS =三甲基甲硅烷基）。
• Expansion of Photocatalytic C(sp³)-H Functionalization to Allylation, Alkynylation, and Imination
  作者：Yi-Lun Shih、Sheng-Hao Huang、Yen-Ku Wu、Ilhyong Ryu

  DOI：10.1246/bcsj.20220171

  日期：2022.10.15

  Photocatalytic C(sp3)-H allylation, alkynylation, and imination using unsaturated benzenesulfonyl compounds were studied using decatungstate anion, W10O324−, as photocatalyst. In all these reactions, site-selective C(sp3)-H bond cleavage was successfully combined with the radical addition/β-scission sequence.

  以十钨酸阴离子 W 10 O 32 4-为光催化剂，研究了使用不饱和苯磺酰基化合物的光催化 C(sp 3 )-H 烯丙基化、炔基化和亚胺化。在所有这些反应中，位点选择性 C(sp 3 )-H 键断裂与自由基加成/β-断裂序列成功结合。
• Nucleophilic substitutions in allylic systems. Further evidence against the existence of the concerted SN2' mechanism
  作者：F. G. Bordwell、Thomas G. Mecca

  DOI：10.1021/ja00771a048

  日期：1972.8