(Z)-1-chloro-4-(2-fluoro-2-phenylvinyl)benzene

• 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: (Z)-1-chloro-4-(2-fluoro-2-phenylvinyl)benzene
• 英文别名: 1-chloro-4-[(Z)-2-fluoro-2-phenylethenyl]benzene
• 化学式: C₁₄H₁₀ClF
• 分子量: 232.685
• InChiKey: JZDIKTOSZTVGKW-UVTDQMKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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

• 作为产物：
  描述：

  (碘乙炔基)苯 在 三乙烯二胺 、 1,3-二碘-5,5-二甲基海因 、 四丁基氟化铵 、 silver(I) acetate 、 palladium diacetate 、 氟化氢吡啶 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙腈 为溶剂， 反应 36.0h， 生成 (Z)-1-chloro-4-(2-fluoro-2-phenylvinyl)benzene
  参考文献：
  名称：

  Silver-Mediated Decarboxylative Fluorodiiodination of Alkynoic Acids: Synthesis of Regio- and Stereoselective Fluoroalkenes

  摘要：

  A variety of arylalkynoic acids reacted with 1,3-diiodo-5,5-dimethylhydantoin and HF.pyridine in the presence of AgOAc to provide the corresponding 1-fluoro-2,2-diiodovinylarenes in good yields and high regioselectivity. In addition, Pd-catalyzed cross-coupling reaction of 1-fluoro-2,2-diiodovinylarenes afforded diaryl coupling products in the Suzuki reaction and monoaryl coupling products with high stereo-selectivity in the Hiyama reaction. It was found that C-F-activated borylation of fluoroalkenes using Pd catalyst afforded the vinylboranes with good yields.

  DOI：

  10.1021/acs.orglett.9b00597

文献信息

• Convergent Synthesis of Fluoroalkenes Using a Dual-Reactive Unit
  作者：Motoyuki Isoda、Yuta Uetake、Tadashi Takimoto、Junpei Tsuda、Takamitsu Hosoya、Takashi Niwa

  DOI：10.1021/acs.joc.0c02474

  日期：2021.1.15

  isostere of amide compounds. To expedite the synthesis of diverse fluoroalkenes, we have developed a dual-reactive C2-unit, (Z)-1-boryl-1-fluoro-2-tosyloxyethene, containing nucleophilic and electrophilic moieties. Consecutive palladium-catalyzed cross-coupling reactions of this unit with aryl bromides and aryl boronic acids allow for the convergent synthesis of diverse trans-1,2-diaryl-substituted fluoroethenes

  氟代烯烃已显示出作为酰胺化合物代谢稳定的等排体的重要性。为了加快各种氟代烯烃的合成，我们开发了一种双反应性C2-单元（Z）-1-硼基-1-氟-2-甲苯磺酰氧基乙烯，其中含有亲核和亲电部分。该单元与芳基溴化物和芳基硼​​酸的连续钯催化的交叉偶联反应允许以化学选择性和立体保持方式聚合合成各种反式-1,2-二芳基取代的氟乙烯。
• Stereoselective formation of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem‑difluoroalkenes with lithium organoborates
  作者：Yisa Xiao、Weichen Huang、Qilong Shen

  DOI：10.1016/j.cclet.2022.01.020

  日期：2022.9

  method for stereoselective construction of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem‑difluoroalkenes in mild conditions was described. The combination of lithium organoborate and ZnBr2 generated in situ lithium aryl zincates, which facilitates the transmetalation step of the nickel-catalyzed cross coupling reaction.

  描述了一种在温和条件下通过镍催化的偕二氟烯烃脱氟偶联立体选择性构建Z-单氟烯烃的方法。有机硼酸锂和ZnBr 2的结合原位生成芳基锌酸锂，这有利于镍催化的交叉偶联反应的金属转移步骤。
• Divergent reactivities in fluoronation of allylic alcohols: synthesis of Z-fluoroalkenes via carbon–carbon bond cleavage
  作者：Tang-Lin Liu、Ji’En Wu、Yu Zhao

  DOI：10.1039/c7sc00483d

  日期：——

  the use of N-fluorobenzenesulfonimide (NFSI) under catalyst-free conditions. By using this simple procedure, a wide range of functionalized Z-fluoroalkenes can be accessed in high yield and selectivity from cyclic and acyclic allylic alcohols.

  在无催化剂条件下使用N-氟苯磺酰亚胺（NFSI）可以诱导烯丙基醇中未应变的碳-碳键非常规断裂。通过使用这种简单的方法，可以从环状和无环烯丙基醇中以高收率和高选择性获得各种官能化的Z-氟代烯烃。
• Gold-Catalyzed Hydrofluorination of Internal Alkynes Using Aqueous HF
  作者：Raphaël Gauthier、Marius Mamone、Jean-François Paquin

  DOI：10.1021/acs.orglett.9b03425

  日期：2019.11.15

  The gold-catalyzed hydrofluorination reaction of internal alkynes using hydrofluoric acid is reported. Notably, those conditions use one of the most economical sources of HF and are free of additional additives. Both symmetrical and unsymmetrical internal alkynes can be utilized, and the use of alkynes bearing a fluorinated group at the propargylic position as substrates allowed for a regioselective

  报道了使用氢氟酸的内部炔烃的金催化的氢氟化反应。值得注意的是，这些条件使用的是最经济的HF来源之一，并且不含其他添加剂。可以使用对称和不对称的内部炔烃，并且使用在炔丙基位置带有氟化基团的炔烃作为底物，可以进行区域选择性氢氟化反应。
• Synthesis of phenyl substituted fluoro-olefins
  作者：Hou-Jen Tsai

  DOI：10.1016/0040-4039(95)02218-x

  日期：1996.1

  The anion derived from diethyl α-fluorobenzyl phosphonate (EtO)2P(O)-CFHPh (2) and lithium diisopropylamide in THF underwent the reaction with aldehydes and ketones to afford a moderate to good yields of phenyl substituted fluoro-olefins RR′C=CFPh (6).

  α-氟代苄基膦酸二乙酯（EtO）2 P（O）-CFHPh（2）和二异丙基氨基化锂在THF中的阴离子与醛和酮反应制得中等至良好收率的苯基取代的氟代烯烃RR'C ＝ CFPh（6）。