[2-(苯磺酰基)-2-氟乙烯基]苯 | 147920-46-5

• 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: [2-(苯磺酰基)-2-氟乙烯基]苯
• 英文名称: 1-fluoro-2-phenyl-1-(phenylsulfonyl)ethene
• 英文别名: [2-(Benzenesulfonyl)-2-fluoroethenyl]benzene；[2-(benzenesulfonyl)-2-fluoroethenyl]benzene
• CAS: 147920-46-5
• 化学式: C₁₄H₁₁FO₂S
• 分子量: 262.305
• InChiKey: MVPGHTIQQVDWLR-UHFFFAOYSA-N

物化性质

• 沸点：
  433.6±45.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 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：
  3

反应信息

• 作为反应物：
  描述：

  [2-(苯磺酰基)-2-氟乙烯基]苯 在 四(三苯基膦)钯 sodium hydroxide 、 偶氮二异丁腈 、 双氧水 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 13.0h， 生成 (Z)-(1-fluoro-2-phenylethenyl)benzene
  参考文献：
  名称：

  Wnuk, Stanislaw F.; Garcia Jr., Pedro I.; Wang, Zhizhong, Organic Letters, 2004, vol. 6, # 12, p. 2047 - 2049

  摘要：

  DOI：
• 作为产物：
  描述：

  二乙基(苯基硫代甲基)磷酸酯 在 Oxone 、 Selectfluor 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 [2-(苯磺酰基)-2-氟乙烯基]苯
  参考文献：
  名称：

  Synthesis of the Multisubstituted Halogenated Olefins via Cross-Coupling of Dihaloalkenes with Alkylzinc Bromides

  摘要：

  The 1-fluoro-1-haloalkenes undergo Pd-catalyzed Negishi cross-couplings with primary alkylzinc bromides to give multisubstituted fluoroalkenes. The alkylation was trans-selective giving pure Z-fluoroalkenes in most cases. The highest yields were obtained with Pd-2(dba)(3) and PdCl2(dppb) catalysts but the best stereochemical outcome was obtained with less reactive Pd(PPh3)(4). The tertiary alkylzincs also produced desired fluoroalkenes in high yields. Coupling of beta,beta-dichloro styrene with organozinc reagent resulted in the formation of monocoupled product.

  DOI：

  10.1021/jo051980e

文献信息

• A metal-free and regioselective approach to (Z)-β-fluorovinyl sulfones and their chemoselective hydrogenation to β-fluoroalkyl sulfones
  作者：Daniel M. Sedgwick、Raquel Román、Pablo Barrio、Cristina Morales、Santos Fustero

  DOI：10.1016/j.jfluchem.2017.12.016

  日期：2018.2

  metal-free hydrofluorination reaction of alkynyl sulfones was developed using TBAF—one of the cheapest and most commonly available fluoride sources. In addition, the reactivity of the resulting β-fluorovinyl sulfones was studied, focusing on their selective hydrogenation reaction. Both β-fluorovinyl sulfones and their hydrogenation products β-fluoroalkyl sulfones may find applications in medicinal and agrochemical

  使用TBAF开发了一种高度区域选择性，无金属的炔基砜氢氟化反应，TBAF是最便宜，最常用的氟化物来源之一。另外，研究了所得β-氟乙烯基砜的反应性，着眼于它们的选择性氢化反应。β-氟乙烯砜及其加氢产物β-氟烷基砜均可在医学和农业化学领域找到应用。
• A new synthesis of α-fluorovinylsulfones utilizing the Peterson olefination methodology
  作者：Noriaki Asakura、Yoshinosuke Usuki、Hideo Iio

  DOI：10.1016/s0022-1139(03)00194-5

  日期：2003.11

  are readily prepared from fluoromethyl phenyl sulfone and the appropriate silyl chloride. The use of TBSCl improves both the stability and yield of 1. Lithium derivatives 4 undergo a smooth Peterson olefination reaction with less-enolizable carbonyl compounds to give moderate to good yields of the expected α-fluorovinylsulfones 6, in some cases with high E-stereoselectivity. One-pot reaction with 4

  α-氟-α-甲硅烷基取代的砜1可以容易地由氟甲基苯基砜和适当的甲硅烷基氯制备。TBSCl的使用可提高1的稳定性和收率。锂衍生物4与不太可烯化的羰基化合物进行平稳的Peterson烯化反应，以中等至良好的产率得到预期的α-氟乙烯基砜6，在某些情况下具有高E-立体选择性。一锅反应与由氟甲基苯基砜在四氢呋喃（THF）中原位生成的4反应也顺利进行，尤其是与醛反应时。
• Radical-mediated thiodesulfonylation of the vinyl sulfones: access to (α-fluoro)vinyl sulfides
  作者：Pablo R. Sacasa、Jessica Zayas、Stanislaw F. Wnuk

  DOI：10.1016/j.tetlet.2009.07.063

  日期：2009.9

  Radical-mediated thiodesulfonylation of the vinyl and (alpha-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (a-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones. (C) 2009 Elsevier Ltd. All rights reserved.
• Wnuk, Stanislaw F.; Garcia Jr., Pedro I.; Wang, Zhizhong, Organic Letters, 2004, vol. 6, # 12, p. 2047 - 2049
  作者：Wnuk, Stanislaw F.、Garcia Jr., Pedro I.、Wang, Zhizhong

  DOI：——

  日期：——
• Synthesis of the Multisubstituted Halogenated Olefins via Cross-Coupling of Dihaloalkenes with Alkylzinc Bromides
  作者：Daniela Andrei、Stanislaw F. Wnuk

  DOI：10.1021/jo051980e

  日期：2006.1.1

  The 1-fluoro-1-haloalkenes undergo Pd-catalyzed Negishi cross-couplings with primary alkylzinc bromides to give multisubstituted fluoroalkenes. The alkylation was trans-selective giving pure Z-fluoroalkenes in most cases. The highest yields were obtained with Pd-2(dba)(3) and PdCl2(dppb) catalysts but the best stereochemical outcome was obtained with less reactive Pd(PPh3)(4). The tertiary alkylzincs also produced desired fluoroalkenes in high yields. Coupling of beta,beta-dichloro styrene with organozinc reagent resulted in the formation of monocoupled product.