(Z)-1-(2-fluoro-2-phenylethenyl)-4-methylbenzene

• 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-(2-fluoro-2-phenylethenyl)-4-methylbenzene
• 英文别名: (Z)-1-(2-fluoro-2-phenylvinyl)-4-methylbenzene；1-[(Z)-2-fluoro-2-phenylethenyl]-4-methylbenzene
• 化学式: C₁₅H₁₃F
• 分子量: 212.267
• InChiKey: ZOYFENOWPAUEPX-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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 ammonium tetrafluoroborate 、 [Pd(IPr)(cin)Cl] 、 [Au(N,N’-bis-[2,6-(di-iso-propyl)phenyl]imidazolidin-2-ylidene)(NEt₃)][HF₂] 、 potassium carbonate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 18.0h， 生成 (Z)-1-(2-fluoro-2-phenylethenyl)-4-methylbenzene
  参考文献：
  名称：

  金（I）和钯（II）N-杂环碳烯配合物催化的炔烃和烯烃的顺序官能化

  摘要：

  据报道，在Au I- NHC（NHC = N-杂环卡宾）催化剂存在下，使用N-碘代琥珀酰亚胺用于合成1-碘代炔烃的末端炔烃加碘。在温和的反应条件下，一系列芳烃成功地以良好的产率转化为相应的1-碘炔烃。通过选择性的Au I催化的氢氟化反应生成（Z）-2-氟-1-碘代烯烃，进一步证明了这些化合物作为有机结构单元的进一步使用以及金属-NHC络合物作为炔烃功能化催化剂的有利选择。由Suzuki–Miyaura与Pd II催化的芳基硼酸交叉偶联‐NHC络合物，可访问三取代（Z）–氟代烯烃。所有方法均可在优化的单个反应条件中仅进行很小的变化即可依次执行，从而在所有情况下均保持高效和高选择性，因此可从市售的末端炔烃中直接获得有价值的氟化烯烃。

  DOI：

  10.1002/cctc.201600868

文献信息

• 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。
• 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）。
• Silver-Mediated Decarboxylative Fluorodiiodination of Alkynoic Acids: Synthesis of Regio- and Stereoselective Fluoroalkenes
  作者：Aravindan Jayaraman、Sunwoo Lee

  DOI：10.1021/acs.orglett.9b00597

  日期：2019.5.17

  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.
• A General and Efficient Route for the Preparation of Phenyl-Substituted Vinyl Fluorides
  作者：Hou-Jen Tsai、Keh-Wen Lin、Tzu-hao Ting、Donald J. Burton

  DOI：10.1002/(sici)1522-2675(19991215)82:12<2231::aid-hlca2231>3.0.co;2-z

  日期：1999.12.15

  alpha-Fluorobenzyl phosphonate (EtO)(2)P(O)CFHPh (2) prepared from diethyl alpha-hydroxyphosphonate (EtO)(2)P(O)CH(OH)Ph (1) and diethylaminosulfur trifluoride (DAST),reacts with bases such as butyllithium, tert-butyllithium, lithium bis(trimethylsilyl)amide, or lithium diisopropylamide at -78 degrees in THF to give the phosphonate carbanion [(EtO)(2)P(O)CFPh]-Li+ (3) which was detected by acylation with propionyl chloride or by addition of MeOD to the reaction mixture to give (EtO)(2)P(O)CF(COEt)Ph (4) and (EtO)(2)P(O)CFDPh (5),respectively. Addition of aldehydes or ketones to a THF solution of carbanion 3 led to moderate-to-good yields of phenyl-substituted vinyl fluorides RR'C=CFPh 6. The stereoselectivity of the products PhCH=CFPh (6a) and Ph(Me)C=CFPh (6i) formed in the reaction was examined. The presence of hexamethylphosphoric triamide or N,N'-dimethylpropyleneurea as cosolvent in the preparation of 6a and 6i increased the (Z)-stereoselectivity. However, the presence of LiCl in THF did not alter the (E)/(Z)-ratio of the product.