1-bromo-1-fluoro-2,2-diphenylethene | 1959-48-4

• 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-1-fluoro-2,2-diphenylethene
• 英文别名: (2-bromo-2-fluoroethene-1,1-diyl)dibenzene；Benzene, 1,1'-(bromofluoroethenylidene)bis-；(2-bromo-2-fluoro-1-phenylethenyl)benzene
• CAS: 1959-48-4
• 化学式: C₁₄H₁₀BrF
• 分子量: 277.136
• InChiKey: KSBCLZVJJXHBND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• 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-bromo-1-fluoro-2,2-diphenylethene 以 环己烷 为溶剂， 反应 16.0h， 以87%的产率得到(2-氟-1-苯基乙烯基)苯
  参考文献：
  名称：

  Photochemistry of organohalogeno-compounds. Part XIX the effect of fluorine on photochemical carbon-halogen bond cleavage

  摘要：

  DOI：

  10.1016/s0022-1139(00)85175-1
• 作为产物：
  描述：

  (2-氟-1-苯基乙烯基)苯 在 溴 作用下， 以 氯仿 为溶剂， 以47%的产率得到1-bromo-1-fluoro-2,2-diphenylethene
  参考文献：
  名称：

  Photochemistry of organohalogeno-compounds. Part XIX the effect of fluorine on photochemical carbon-halogen bond cleavage

  摘要：

  DOI：

  10.1016/s0022-1139(00)85175-1

文献信息

• A Simple, Two-Step, Site-Specific Preparation of Fluorinated Naphthalene and Phenanthrene Derivatives from Fluorobromo-Substituted Alkenes
  作者：Yi Wang、Jianjun Xu、Donald J. Burton

  DOI：10.1021/jo061305k

  日期：2006.9.1

  two-step procedure for the site-specific preparation of fluorinated naphthalene and phenanthrene derivatives is described. The Sonogashira reaction of bromofluoro-substituted alkenes with terminal alkynes, followed by base-catalyzed cyclization in refluxing N-methyl-2-pyrrolidinone (NMP), affords the corresponding fluorinated naphthalene and phenanthrene derivatives in good yields.

  描述了一种用于现场具体制备氟化萘和菲衍生物的简便的两步程序。溴氟取代的烯烃与末端炔烃的Sonogashira反应，然后在回流的N-甲基-2-吡咯烷酮（NMP）中进行碱催化的环化反应，以良好的收率得到相应的氟化萘和菲衍生物。
• Visible-light-mediated defluorinative cross-coupling of <i>gem</i>-difluoroalkenes with thiols
  作者：Junlei Wang、Binbin Huang、Chao Yang、Wujiong Xia

  DOI：10.1039/c9cc05293c

  日期：——

  Here we report a visible-light-mediated monofluoroalkenylation through defluorinative cross-coupling of gem-difluoroalkenes with aryl, benzyl, and alkyl thiols.

  我们在这里报告了一种可见光介导的单氟烯烃化反应，通过将gem-二氟烯烃与芳基、苄基和烷基硫醇进行脱氟交叉偶联。
• Palladium-Catalyzed Cross-Coupling of Gem-Bromofluoroalkenes with Alkylboronic Acids for the Synthesis of Alkylated Monofluoroalkenes
  作者：Laëtitia Chausset-Boissarie、Nicolas Cheval、Christian Rolando

  DOI：10.3390/molecules25235532

  日期：——

  versatile fluorinated synthons in organic synthesis, medicinal chemistry and materials science. In light of the importance of alkyl-substituted monofluoroalkenes efficient synthesis of these moieties still represents a synthetic challenge. Herein, we described a mild and efficient methodology to obtain monofluoroalkenes through a stereospecific palladium-catalyzed alkylation of gem-bromofluoroalkenes with

  单氟烯烃是有机合成、药物化学和材料科学中的多功能氟化合成子。鉴于烷基取代的单氟烯烃的重要性，这些部分的有效合成仍然是合成挑战。在此，我们描述了一种温和而有效的方法，通过在温和条件下通过立体有择钯催化的溴氟烯烃与伯和应变仲烷基硼酸的烷基化来获得单氟烯烃。这种新颖的策略可以高产率地获得各种功能化的三取代和四取代的单氟烯烃，具有良好的官能团耐受性，独立于嵴溴氟烯烃的几何形状。
• Low-temperature 19F NMR spectroscopy of 1-fluoro-1-lithioethenes
  作者：Jaroslav Kvı́čala、Richard Hrabal、Jiřı́ Czernek、Ivana Bartošová、Oldřich Paleta、Andrew Pelter

  DOI：10.1016/s0022-1139(01)00553-x

  日期：2002.2

  1-fluoro-1-lithioethenes bearing hydrogen, fluorine, phenyl, and/or dimethylphenylsilyl groups in the β-positions have been determined by a low-temperature 19F NMR spectroscopy. Some 1-fluoro-1-lithioethenes displayed an exceptionally low value of the trans-3JFF coupling constant. Stereoselectivity of carbenoid formation, as well as an effect of configuration on the stability is discussed.

  已经通过低温19 F NMR光谱测定了在β位置带有氢，氟，苯基和/或二甲基苯基甲硅烷基的稳定化的1-氟-1-硫代乙烯的半衰期和氟原子位移。一些1-氟-1- lithioethenes显示的异常低的值的反式- 3 Ĵ FF偶合常数。讨论了类胡萝卜素形成的立体选择性以及构型对稳定性的影响。
• A Facile and Mild Method for the Synthesis of Terminal Bromofluoroolefins via Diethylzinc-Promoted Wittig Reaction
  作者：Xinsheng Lei、Guillaume Dutheuil、Xavier Pannecoucke、Jean-Charles Quirion

  DOI：10.1021/ol049742d

  日期：2004.6.1

  Synthesis of 1-bromo-1-fluoroolefins was achieved in good yields via a Wittig reaction promoted by diethylzinc, even with nonactivated aldehydes and ketones as starting materials.