1-fluoro-2-phenylvinyl chloride | 260262-17-7

• 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-fluoro-2-phenylvinyl chloride
• 英文别名: 1-chloro-1-fluoro-2-phenylethene；(2-Fluor-2-chlor-vinyl)-benzol；cis/trans-β-Chlor-β-fluorstyrol；1-Chlor-1-fluor-2-phenylaethylen；(2-Chloro-2-fluoroethenyl)benzene
• CAS: 260262-17-7
• 化学式: C₈H₆ClF
• 分子量: 156.587
• InChiKey: DNOFXVCVFOOHTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-fluoro-2-phenylvinyl chloride 、 bromo(4-ethoxy-4-oxobutyl)zinc 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 10.0h， 以80%的产率得到ethyl 5-fluoro-6-phenyl-5(Z)-hexenoate
  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
• 作为产物：
  描述：

  2,2-difluoro-2-chloro-1-phenylethane 在 potassium tert-butylate 作用下， 以 叔丁醇 为溶剂， 生成 1-fluoro-2-phenylvinyl chloride
  参考文献：
  名称：

  Proton-transfer reactions. II. Effects of internal return on reactivity difference between alkoxide-promoted eliminations in tert-butyl alcohol and ethyl alcohol

  摘要：

  DOI：

  10.1021/ja00408a024

文献信息

• Preparation and synthetic utility of fluorinated phosphonium salts, -phosphonium salts and phosphoranium salts [1]
  作者：Donald J. Burton

  DOI：10.1016/s0022-1139(00)81218-x

  日期：1983.10

  fluorohalomethanes provides a rapid and high yield synthesis of various types of fluorinated phosphonium salts, bis-phosphonium salts and phosphoranium salts. These salts are useful precursors to fluorine-containing ylides, carbenes and methide ions. Examples of the preparation, mechanism of formation, and synthetic utility of these novel reagents is described.

  叔膦与氟代卤甲烷的反应提供了各种类型的氟化phospho盐，双-盐和phosphor盐的快速且高产率的合成。这些盐是有用的含氟烷基化物，卡宾和甲基离子的前体。描述了这些新型试剂的制备，形成机理和合成效用的实例。
• Synthesis of fluorinated olefins via the palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides with organoboranes
  作者：Chen Chen、Keith Wilcoxen、Nathalie Strack、James R. McCarthy

  DOI：10.1016/s0040-4039(98)02589-1

  日期：1999.1

  The palladium catalyzed cross-coupling reaction of 1-fluorovinyl halides 1–4 with organoboranes proceeds under Suzuki conditions with retention on configuration to give 1-substituted 1-fluoroolefins 6–8 in good to excellent yields.

  1-氟乙烯基卤化物1-4与有机硼烷的钯催化交叉偶联反应在Suzuki条件下进行，并保留构型，从而以极好的收率得到1-取代的1-氟烯烃6-8。
• A Novel Approach to 2-Chloro-2-fluorostyrenes
  作者：Valentine G. Nenajdenko、Alexey V. Shastin、Vasily N. Korotchenko、Georgy N. Varseev、Elisabeth S. Balenkova

  DOI：10.1002/ejoc.200390033

  日期：2003.1

  A new general catalytic olefination reaction (COR) of aromatic and heteroaromatic aldehydes and ketones was applied to synthesise 2-chloro-2-fluorostyrenes. The two-stage procedure includes the transformation of carbonyl compounds into hydrazones followed by treatment with CFCl3 mediated by copper catalysis. Trichlorofluoromethane was used as a chlorofluoromethylene transfer reagent. The reaction proceeds

  一种新的芳香族和杂芳香族醛和酮的通用催化烯化反应 (COR) 被应用于合成 2-氯-2-氟苯乙烯。两阶段程序包括将羰基化合物转化为腙，然后在铜催化下用 CFCl3 处理。三氯氟甲烷用作氯氟亚甲基转移试剂。该反应立体选择性地进行，以高产率获得目标烯烃。讨论了建议的反应机理。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Fluoro olefins. III. Synthesis of .beta.-substituted 1-chloroperfluoro olefins
  作者：Donald J. Burton、Henry C. Krutzsch

  DOI：10.1021/jo00832a005

  日期：1970.7
• Proton-transfer reactions. II. Effects of internal return on reactivity difference between alkoxide-promoted eliminations in tert-butyl alcohol and ethyl alcohol
  作者：H. F. Koch、W. Tumas、R. Knoll

  DOI：10.1021/ja00408a024

  日期：1981.9