4-carbethoxy-α-chloro-β,β-difluorostyrene

• 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: 4-carbethoxy-α-chloro-β,β-difluorostyrene
• 英文别名: Ethyl 4-(1-chloro-2,2-difluoroethenyl)benzoate
• 化学式: C₁₁H₉ClF₂O₂
• 分子量: 246.641
• InChiKey: CGAYHVYYODXTPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氟烷 、 对碘苯甲酸乙酯 在 四(三苯基膦)钯 仲丁基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 正己烷 、 环己烷 为溶剂， 反应 1.0h， 以83%的产率得到4-carbethoxy-α-chloro-β,β-difluorostyrene
  参考文献：
  名称：

  Reaction of Halothane with sec-butyllithium in the presence of zinc halides—one-pot preparation of chlorodifluorovinylzinc reagent and its derivatization to α-chloro-β,β-difluorostyrene

  摘要：

  Halothane. 2-bromo-2-chloro-1,1,1-trifluoroethane, reacts with sec-butyllithium in the presence of zinc halides to afford a chlorodifluorovinylzinc reagent. This zinc reagent reacts with aryl halides in the presence of a palladium catalyst to give chlorodifluorostyrene derivatives in moderate to good yields. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(03)00053-8

文献信息

• The room temperature preparation of the 1-chloro-2,2-difluorovinylzinc reagent from HCFC-133a (CF3CH2Cl). The first ambient, high yield, one-flask preparation of α-chloro-β,β-difluorostyrenes
  作者：R. Anilkumar、Donald J. Burton

  DOI：10.1016/s0040-4039(02)01591-5

  日期：2002.9

  65–85% isolated yields of ArCClCF2. This one-flask procedure provides the first room temperature generation of the 1-chloro-2,2-difluorovinylzinc reagent and the first high yield preparation of α-chloro-β,β-difluorostyrenes from a cheap, readily available industrial precursor.

  LDA（2.0当量）与ZnCl 2（1.0当量）和HCFC-133a（CF 3 CH 2 Cl）（1.0当量）的THF溶液在15–20°C下反应，产生91％的[ ˚F 2 ]CCClZnCl。在室温下将ArI和Pd（PPh 3）4添加到65°C，可分离出65-85％的ArCCl 3 CF 2产率。这种单烧瓶方法提供了在室温下首次生成1-氯-2,2-二氟乙烯基锌试剂，以及从廉价的易得的工业前体中首次高产率制备α-氯-β，β-二氟苯乙烯的方法。
• Room temperature preparation of α-chloro-β,β-difluoroethenylzinc reagent (CF2CClZnCl) by the metallation of HCFC-133a (CF3CH2Cl) and a high yield one-pot synthesis of α-chloro-β,β-difluorostyrenes
  作者：R. Anilkumar、Donald J. Burton

  DOI：10.1016/j.jfluchem.2005.03.021

  日期：2005.5

  alpha-Chloro-beta,beta-difluorovinylzinc reagent [CF2=CClZnCl] was generated in 91% yield by the metallation of a THF solution of commercially available HCFC-133a (CF3CH2Cl) and zinc chloride at 15-20 degrees C using LDA as base. The corresponding reaction with Halothane (TM) (CF3CHClBr) produced a poor yield of CF2=CClZnCl. The palladium catalyzed coupling reaction of the CF2=CClZnCl with aryl iodides under mild reaction conditions produced alpha-chloro-beta,beta-difluorostyrenes in 64-90% isolated yields. The stability of the intermediate CF2=CClLi and the nature of the zinc reagents are discussed. (c) 2005 Elsevier B.V. All rights reserved.
• Reaction of Halothane with sec-butyllithium in the presence of zinc halides—one-pot preparation of chlorodifluorovinylzinc reagent and its derivatization to α-chloro-β,β-difluorostyrene
  作者：Masakazu Nishihara、Yuki Nakamura、Naoki Maruyama、Kazuyuki Sato、Masaaki Omote、Akira Ando、Itsumaro Kumadaki

  DOI：10.1016/s0022-1139(03)00053-8

  日期：2003.8

  Halothane. 2-bromo-2-chloro-1,1,1-trifluoroethane, reacts with sec-butyllithium in the presence of zinc halides to afford a chlorodifluorovinylzinc reagent. This zinc reagent reacts with aryl halides in the presence of a palladium catalyst to give chlorodifluorostyrene derivatives in moderate to good yields. (C) 2003 Elsevier Science B.V. All rights reserved.