1-bromo-2-phenylethenyl phenyl sulfone | 65210-94-8

• 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-bromo-2-phenylethenyl phenyl sulfone
• 英文别名: (Z)-1-bromo-2-phenyl-1-phenylsulphonylethene；(Z)-1-(benzenesulfonyl)-1-bromo-2-phenylethene；[(Z)-2-(benzenesulfonyl)-2-bromoethenyl]benzene
• CAS: 65210-94-8
• 化学式: C₁₄H₁₁BrO₂S
• 分子量: 323.21
• InChiKey: BMWXSXLPGQMDIV-SDNWHVSQSA-N

物化性质

• 熔点：
  101-103 °C(Solv: ethanol (64-17-5))
• 沸点：
  474.4±45.0 °C(Predicted)
• 密度：
  1.516±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1-bromo-2-phenylethenyl phenyl sulfone 、 苯甲酰氯 在 异丙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以62%的产率得到(E)-1,3-diphenyl-2-(phenylsulfonyl)prop-2-en-1-one
  参考文献：
  名称：

  Preparation of functionalized alkenylmagnesium bromides via a bromine–magnesium exchange

  摘要：

  alpha-Bromonitriles, such as 1, 2 or the alpha-bromosulfone 3, undergo a smooth bromine-magnesium exchange with isopropylmagnesium bromide furnishing new functionalized organomagnesium species which react smoothly with various electrophiles like Me3SiCl, Bu3SnCl, allyl bromides, aldehydes, ketones or acid chlorides providing the expected products of type 7, 8 or 9. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00387-7
• 作为产物：
  描述：

  phenyl (Z)-β-styryl sulphone 生成 1-bromo-2-phenylethenyl phenyl sulfone
  参考文献：
  名称：

  Carlier,P. et al., Canadian Journal of Chemistry, 1977, vol. 55, p. 3190 - 3201

  摘要：

  DOI：

文献信息

• Preparation and ring-opening reactions of 2-phenylsulphonyl-2-trimethylsilyl-oxiranes
  作者：Cheryl T. Hewkin、Richard F.W. Jackson

  DOI：10.1016/s0040-4039(00)98809-9

  日期：1990.1

  trimethylsilyl oxiranes(2), which on treatment with MgBr2Et2O gave 2-bromoacylsilanes(3) and either bromovinyl sulphones(5) or α,β-unsaturated acylsilanes(6) and 2-trimethylsilyl car☐ylic acids(7), depending on structure.

  在氯代三甲基硅烷存在下，2-苯基磺酰基肟基（1）与丁基锂反应生成2-苯基磺酰基-2-三甲基甲硅烷基肟基（2），经MgBr 2 Et 2 O处理后生成2-溴酰基硅烷（3）和两种溴化砜基（ 5）或α，β-不饱和酰基硅烷（6）和2-三甲基甲硅烷基羧基丙烯酸（7），具体取决于结构。
• Preparation of α-functionalized alkenylmagnesium reagents via a halide–magnesium exchange
  作者：Jérôme Thibonnet、Viet Anh Vu、Laurent Bérillon、Paul Knochel

  DOI：10.1016/s0040-4020(02)00439-8

  日期：2002.6

  A general preparation of alkenylmagnesium derivatives bearing an electron-withdrawing function in the alpha-position (Y=CN, CO2R, CONR2, SO2Ph) has been made possible by using a low temperature (-40 to -30degreesC) bromine-magnesium exchange with i-PrMgBr in THF. This reaction has also been used to prepare 5-magnesiated-1,3-dioxin-4-one derivatives bearing an alkoxy substituent in beta-position to the carbon-magnesium bond. (C) 2002 Published by Elsevier Science Ltd.
• Hewkin, Cheryl T.; Jackson, Richard F. W., Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3103 - 3112
  作者：Hewkin, Cheryl T.、Jackson, Richard F. W.

  DOI：——

  日期：——
• Reaction of 1-bromovinyl and 1-bromo-2-phenylvinyl sulfones with some CH acids
  作者：V. A. Vasin、I. Yu. Bolusheva、V. A. Kalyazin、V. V. Razin

  DOI：10.1134/s1070428014100091

  日期：2014.10

  Benzyl, methyl, and phenyl alpha-bromovinyl sulfones reacted with malononitrile and dimethyl malonate sodium enolates in THF to give sulfonyl-substituted cyclopropanes. Reactions of the same sulfones with methyl acetoacetate sodium enolate afforded the corresponding sulfonyl-substituted cyclopropanes as mixtures of cis and trans isomers with a small impurity of 5-sulfonyl-4,5-dihydrofuran derivative. Phenyl and p-tolyl 1-bromo-2-phenylvinyl sulfones reacted with methyl acetoacetate sodium salt to produce a mixture of trans-isomeric 5-sulfonyl-4,5-dihydrofuran and Michael adduct of the CH acid with activated acetylene generated by concurrent 1,2-dehydrobromination of the initial alpha-bromovinyl sulfone.
• HEWKIN, CHERYL T.;JACKSON, RICHARD F. W., TETRAHEDRON LETT., 31,(1990) N3, C. 1877-1880
  作者：HEWKIN, CHERYL T.、JACKSON, RICHARD F. W.

  DOI：——

  日期：——