(1,1-difluoro-2-phenylethyl)zinc(II) bromide | 1422039-14-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1,1-difluoro-2-phenylethyl)zinc(II) bromide
• CAS: 1422039-14-2
• 化学式: C₈H₇BrF₂Zn
• 分子量: 286.434
• InChiKey: CPMQQRYJUWFXCQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.21
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (1,1-difluoro-2-phenylethyl)zinc(II) bromide 在 溴 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以5.65 mg的产率得到(2-bromo-2,2-difluoroethyl)benzene
  参考文献：
  名称：

  Reactions of organozinc reagents with potassium bromodifluoroacetate

  摘要：

  A practical method for the synthesis of gem-difluorinated compounds from organozinc reagents is described. Potassium bromodifluoroacetate serves as a source of CF2-fragment, which is inserted into carbon zinc bond of organozinc reagents. The intermediate difluorinated organozinc species can be protonated, brominated or coupled with allylic electrophiles. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.08.021
• 作为产物：
  描述：

  溴甲苯 在 四乙基溴化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.75h， 生成 (1,1-difluoro-2-phenylethyl)zinc(II) bromide
  参考文献：
  名称：

  Reactions of organozinc reagents with potassium bromodifluoroacetate

  摘要：

  A practical method for the synthesis of gem-difluorinated compounds from organozinc reagents is described. Potassium bromodifluoroacetate serves as a source of CF2-fragment, which is inserted into carbon zinc bond of organozinc reagents. The intermediate difluorinated organozinc species can be protonated, brominated or coupled with allylic electrophiles. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.08.021

文献信息

• Reactions of Difluorocarbene with Organozinc Reagents
  作者：Vitalij V. Levin、Artem A. Zemtsov、Marina I. Struchkova、Alexander D. Dilman

  DOI：10.1021/ol400122k

  日期：2013.2.15

  Reactions of difluorocarbene with benzyl and alkylzinc halides leading to fluorinated organozinc species have been described. The generated α-difluorinated organozinc reagents are reasonably stable in solution and can be quenched with external electrophiles (iodine, bromine, proton), affording compounds containing the CF2 fragment.

  已经描述了二氟卡宾与苄基和烷基锌卤化物的反应导致氟化的有机锌物质的反应。生成的α-二氟有机锌试剂在溶液中相当稳定，可以用外部亲电试剂（碘，溴，质子）淬灭，得到含有CF 2片段的化合物。
• Coupling of gem -difluorinated organozinc reagents with S-electrophiles
  作者：Salavat S. Ashirbaev、Vitalij V. Levin、Marina I. Struchkova、Alexander D. Dilman

  DOI：10.1016/j.jfluchem.2016.07.018

  日期：2016.11

  gem-Difluorinated organozinc reagents, which were prepared by insertion of CF2-fragment into CZn bond, couple with diethyl dixanthogen, di(benzothiazolyl) disulfide, and tetraethylthiuram disulfide. The reaction is promoted either by a copper(I) catalyst or by irradiation with blue light in the presence of Eosin Y disodium salt.

  宝石-二氟有机锌试剂，其通过将CF 2片段插入C Zn键，与二乙基二黄原酮，二（苯并噻唑基）二硫化物和四乙基秋兰姆二硫化物偶联而制备。在曙红Y二钠盐存在下，通过铜（I）催化剂或通过蓝光照射促进反应。
• Coupling of N -acyliminium chlorides with gem -difluorinated organozinc reagents
  作者：Vitalij V. Levin、Marina I. Struchkova、Alexander D. Dilman

  DOI：10.1016/j.mencom.2017.03.010

  日期：2017.3

  CuCl-catalyzed coupling of N-acyliminium chlorides (generated from imines and acyl chlorides) with gem-difluorinated organozincs affords N-(2,2-difluoroalkyl)carboxamides in moderate yield.

  CuCl催化的N-酰氯氯化物（由亚胺和酰氯生成）与宝石二氟化有机锌的偶联以适中的产率提供N-（2,2-二氟烷基）羧酰胺。
• Reaction of gem-difluorinated organozinc reagents with β-nitrostyrenes
  作者：Nikolay S. Kondratyev、Vitalij V. Levin、Artem A. Zemtsov、Marina I. Struchkova、Alexander D. Dilman

  DOI：10.1016/j.jfluchem.2015.06.001

  日期：2015.8

  A novel reactivity pattern of gem-difluorinated organozincs in copper(I) catalyzed reaction with β-nitrostyrenes is described. The reaction proceeds not as conjugate addition, but as nitro group substitution furnishing alkenes as single E-isomers in moderate yields.

  描述了一种新的宝石二氟有机锌在铜（I）与β-硝基苯乙烯催化反应中的反应模式。该反应不是作为共轭加成进行的，而是作为硝基取代进行的，以中等收率提供了作为单一E-异构体的烯烃。
• Copper-Catalyzed Coupling of Acyl Chlorides with <i>gem</i>-Difluorinated Organozinc Reagents via Acyl Dithiocarbamates
  作者：Salavat S. Ashirbaev、Vitalij V. Levin、Marina I. Struchkova、Alexander D. Dilman

  DOI：10.1021/acs.joc.7b02598

  日期：2018.1.5

  A cross-coupling of acyl chlorides with gem-difluorinated organozinc reagents affording difluorinated ketones is described. In the reaction, acyl chlorides are first treated with potassium dithiocarbamate to generate S-acyl dithiocarbamates, which couple with organozincs in the presence of a copper(I) catalyst.

  描述了酰氯与提供二氟化酮的宝石-二氟化有机锌试剂的交叉偶联。在该反应中，首先用二硫代氨基甲酸钾处理酰氯，生成S-酰基二硫代氨基甲酸酯，然后在铜（I）催化剂存在下将其与有机锌偶联。