(E)-1,2-双(苯基磺酰基)-2-丁烯 | 122521-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (E)-1,2-双(苯基磺酰基)-2-丁烯
• 英文名称: (E)-1,2-bis(phenylsulfonyl)-2-butene
• 英文别名: 1,1'-(2-Butene-1,2-diyldisulfonyl)dibenzene；[(E)-2-(benzenesulfonyl)but-2-enyl]sulfonylbenzene
• CAS: 122521-49-7
• 化学式: C₁₆H₁₆O₄S₂
• 分子量: 336.433
• InChiKey: CJKQKQQDUSCLEK-JLZUIIAYSA-N

物化性质

• 熔点：
  137-138 °C
• 沸点：
  579.9±50.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  (E)-1,2-双(苯基磺酰基)-2-丁烯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以88%的产率得到2-丁炔基苯基砜
  参考文献：
  名称：

  Cycloaddition of (phenylsulfonyl)-1,2-propadienes with diazomethane. Novel rearrangement reactions of the resulting cycloadducts

  摘要：

  The cycloaddition reactions of several phenylsulfonyl-substituted allenes with diazomethane have been investigated. The major products formed were identified as 3-(phenylsulfonyl)-4-methylene-2-pyrazolines. These pyrazolines engage in a variety of mechanistically interesting transformations, ranging from base-catalyzed rearrangements to addition of Grignard reagents. The dipolar cycloadduct derived from the reaction of diazomethane with 3-(phenylsulfonyl)-1,2-butadiene undergoes a 1,3-phenylsulfonyl shift upon irradiation to give 3-methyl-4-[(phenylsulfonyl)methyl]pyrazole. The cycloadduct derived from there action of 2,3-bis(phenylsulfonyl)-1-propene with diazomethane readily loses nitrogen upon photolysis to give 1-[(phenylsulfonyl)methyl]-1-(phenylsulfonyl)cyclopropane. This cyclopropane affords a variety of novel rearranged structures when treated with several different bases. The products obtained can be rationalized in terms of a base-catalyzed rearrangement of the above cyclopropane to a-methyl(phenylsulfonyl)allene which reacts further with the particular base used to produce the observed products.

  DOI：

  10.1021/jo00060a021
• 作为产物：
  描述：

  1-(phenylsulfonyl)propyne 在 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 12.25h， 生成 (E)-1,2-双(苯基磺酰基)-2-丁烯
  参考文献：
  名称：

  Generation and cycloaddition reactions of phenylsulfonyl-substituted 1,3-butadienes

  摘要：

  DOI：

  10.1021/jo00278a049

文献信息

• [3 + 2] Cyclization-elimination route to cyclopentenyl sulfones using (phenylsulfonyl)-1,2-propadiene
  作者：Albert Padwa、Philip E. Yeske

  DOI：10.1021/jo00022a032

  日期：1991.10

  Treatment of (phenylsulfonyl)-1,2-propadiene (1) with bis(phenylsulfonyl)methane in the presence of sodium hydride affords 2,4,4-tris(phenylsulfonyl)-1-butene in 94% yield. Similar rearranged products were obtained using other soft nucleophiles and related allenes. The formation of these products involves addition of benzenesulfinate anion onto allene 1. The initially formed carbanion undergoes proton transfer with bis(phenylsulfonyl)methane followed by a S(N)2' reaction of the resulting anion with 2,3-bis(phenylsulfonyl)-1-propene. Supporting evidence for the proposed mechanism is provided by the observation that the reaction of dimethyl malonate with the activated allene in the presence of sodium benzenesulfinate gives mostly abnormal products. When allene 1 is allowed to react with olefins bearing an electron-withdrawing group in the presence of sodium benzenesulfinate, a substituted cyclopentenyl sulfone is formed. The reaction proceeds in a stepwise fashion by addition of the initially produced carbanion onto the activated pi-bond of the olefin followed by a 5-endo-trig cyclization and elimination of benzenesulfinate. This approach represents a mild and versatile anionic [3 + 2] route to five-membered unsaturated sulfones.
• PADWA, ALBERT;HARRISON, BRIAN;MURPHREE, S. SHAUN;YESKE, PHILIP E., J. ORG. CHEM., 54,(1989) N7, C. 4232-4235
  作者：PADWA, ALBERT、HARRISON, BRIAN、MURPHREE, S. SHAUN、YESKE, PHILIP E.

  DOI：——

  日期：——
• Cycloaddition of (phenylsulfonyl)-1,2-propadienes with diazomethane. Novel rearrangement reactions of the resulting cycloadducts
  作者：Albert Padwa、Michelle A. Filipkowski、Donald N. Kline、S. Shaun Murphree、Philip E. Yeske

  DOI：10.1021/jo00060a021

  日期：1993.4

  The cycloaddition reactions of several phenylsulfonyl-substituted allenes with diazomethane have been investigated. The major products formed were identified as 3-(phenylsulfonyl)-4-methylene-2-pyrazolines. These pyrazolines engage in a variety of mechanistically interesting transformations, ranging from base-catalyzed rearrangements to addition of Grignard reagents. The dipolar cycloadduct derived from the reaction of diazomethane with 3-(phenylsulfonyl)-1,2-butadiene undergoes a 1,3-phenylsulfonyl shift upon irradiation to give 3-methyl-4-[(phenylsulfonyl)methyl]pyrazole. The cycloadduct derived from there action of 2,3-bis(phenylsulfonyl)-1-propene with diazomethane readily loses nitrogen upon photolysis to give 1-[(phenylsulfonyl)methyl]-1-(phenylsulfonyl)cyclopropane. This cyclopropane affords a variety of novel rearranged structures when treated with several different bases. The products obtained can be rationalized in terms of a base-catalyzed rearrangement of the above cyclopropane to a-methyl(phenylsulfonyl)allene which reacts further with the particular base used to produce the observed products.
• Generation and cycloaddition reactions of phenylsulfonyl-substituted 1,3-butadienes
  作者：Albert Padwa、Brian Harrison、S. Shaun Murphree、Philip E. Yeske

  DOI：10.1021/jo00278a049

  日期：1989.8