3-Phenyl-penta-1,2-dienylsulfonyl-benzene | 112882-24-3

• 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: 3-Phenyl-penta-1,2-dienylsulfonyl-benzene
• CAS: 112882-24-3
• 化学式: C₁₇H₁₆O₂S
• 分子量: 284.379
• InChiKey: BQABNIKEZKBBEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  62 °C(Solv: ligroine (8032-32-4))
• 沸点：
  482.2±28.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Phenyl-penta-1,2-dienylsulfonyl-benzene 在 水 、 溴 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.08h， 以80%的产率得到E-1-(phenylsulfonyl)-2-bromo-3-phenyl-1(E),3(E)-pentadiene
  参考文献：
  名称：

  Studies on electrophilic reaction of Br2 with 1,2-allenylic sulfones. A highly regio- and stereoselective synthesis of 1-phenylsulfonyl-2-bromo-1(E)-alken-3-ols and 1-phenylsulfonyl-2-bromo-1(E),3(E)-butadienes

  摘要：

  The reaction of 1,2-allenyl sulfones with Br-2 afforded E-bromohydroxylation- or E-bromination-elimination products highly regio-and stereoselectively depending on the substitution pattern of the allene functionality. The five-membered intermediate cis-3h was isolated and characterized by X-ray diffraction study. The study on its reactivity of this intermediate revealed the origin of the regio-and stereoselectivity of this reaction. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.05.039
• 作为产物：
  描述：

  2-苯基-1-丁烯-1-酮 、 苯砜基甲基膦酸二乙酯 在 sodium hydride 作用下， 生成 3-Phenyl-penta-1,2-dienylsulfonyl-benzene
  参考文献：
  名称：

  A Direct and Efficient Synthesis of Allenyl Sulfones by the Horner-Wittig Reaction

  摘要：

  烯丙基磺醚是通过二乙基甲基（或芳基）磺酰基甲基磷酸酯阴离子与酮烯的霍纳-威蒂格反应直接制备的。该方法在苯乙烯和二苯酮的反应中分别获得了优良到中等的产率，后者对碱性介质更为敏感。

  DOI：

  10.1055/s-1987-28052

文献信息

• Observation of the First Heck-Type Cross-Coupling Reaction of Allenes with Aryl Halides. Synthesis of Polysubstituted 1,2-Allenyl Sulfones
  作者：Chunling Fu、Shengming Ma

  DOI：10.1021/ol050301j

  日期：2005.4.14

  [reaction: see text] The Heck-type allenylation of aryl halides with allenes has been observed for the first time: The regioselectivity of intermolecular carbopalladation of 1,2-allenyl sulfones affording vinylic Pd intermediates is completely opposite to what was reported in the literature.

  [反应：见正文]首次观察到芳基卤化物与烯丙基的Heck型烯丙基化：提供乙烯基Pd中间体的1,2-烯基砜的分子间碳钯反应的区域选择性与文献报道完全相反。
• A Direct and Efficient Synthesis of Allenyl Sulfones by the Horner-Wittig Reaction
  作者：Houda Fillion、Ali Hseine、Marie-Hélène Pera、Véronique Dufaud、Bernard Refouvelet

  DOI：10.1055/s-1987-28052

  日期：——

  Allenic sulfones are directly prepared by the Horner-Wittig reaction of diethyl methyl(or aryl)sulfonylmethylphosphonate anions with ketenes. The method affords excellent to moderate yields respectively with phenylethyl and diphenylketene, the latter being more sensitive to basic media.

  烯丙基磺醚是通过二乙基甲基（或芳基）磺酰基甲基磷酸酯阴离子与酮烯的霍纳-威蒂格反应直接制备的。该方法在苯乙烯和二苯酮的反应中分别获得了优良到中等的产率，后者对碱性介质更为敏感。
• FILLION, H.;REFOUVELET, B.;PERA, M. H.;DUFAUD, V., SYNTH. COMMUN., 19,(1989) N9, C. 3343-3348
  作者：FILLION, H.、REFOUVELET, B.、PERA, M. H.、DUFAUD, V.

  DOI：——

  日期：——
• FILLION H.; HSEINE A.; PERA M. -H.; DUFAND V.; REFOUVELET B., SYNTHESIS,(1987) N 8, 708-709
  作者：FILLION H.、 HSEINE A.、 PERA M. -H.、 DUFAND V.、 REFOUVELET B.

  DOI：——

  日期：——
• Studies on electrophilic reaction of Br2 with 1,2-allenylic sulfones. A highly regio- and stereoselective synthesis of 1-phenylsulfonyl-2-bromo-1(E)-alken-3-ols and 1-phenylsulfonyl-2-bromo-1(E),3(E)-butadienes
  作者：Chao Zhou、Chunling Fu、Shengming Ma

  DOI：10.1016/j.tet.2007.05.039

  日期：2007.8

  The reaction of 1,2-allenyl sulfones with Br-2 afforded E-bromohydroxylation- or E-bromination-elimination products highly regio-and stereoselectively depending on the substitution pattern of the allene functionality. The five-membered intermediate cis-3h was isolated and characterized by X-ray diffraction study. The study on its reactivity of this intermediate revealed the origin of the regio-and stereoselectivity of this reaction. (C) 2007 Published by Elsevier Ltd.