(Z)-1-fluoro-1,2-diphenylpropene | 1493-87-4

• 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-fluoro-1,2-diphenylpropene
• 英文别名: (Z)-(1-fluoro-2-methyl-2-phenylethenyl)benzene；(Z)-(1-fluoroprop-1-ene-1,2-diyl)dibenzene；1t-fluoro-1c,2-diphenyl-propene；1t-Fluor-1c,2-diphenyl-propen；[(Z)-1-fluoro-1-phenylprop-1-en-2-yl]benzene
• CAS: 1493-87-4
• 化学式: C₁₅H₁₃F
• 分子量: 212.267
• InChiKey: ALDZLGXDNCOHFW-QINSGFPZSA-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：
  0.07
• 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：

  1,1-difluoro-1,2-diphenyl-propane 在 氢氧化钾 作用下， 生成 (Z)-1-fluoro-1,2-diphenylpropene
  参考文献：
  名称：

  Rearrangement Accompanying the Addition of Fluorine to 1,1-Diarylethylenes

  摘要：

  DOI：

  10.1021/ja00894a016

文献信息

• 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）。
• Copper(I)-Mediated Borofluorination of Alkynes
  作者：Abraham J. Jordan、Percie K. Thompson、Joseph P. Sadighi

  DOI：10.1021/acs.orglett.8b02195

  日期：2018.9.7

  fluoroalkene formation. Alkynes can be converted to cis-(β-fluorovinyl)boronates by a reaction with an (NHC)copper(I) boryl generated in situ, followed by N-fluorobenzenesulfonimide (NFSI). This sequence gives rise to anti-Markovnikov fluorination products from terminal alkynes. Oxidation of a cis-(β-fluorovinyl)trifluoroboronate yields an α-fluoroketone, whereas a palladium-catalyzed Suzuki–Miyaura

  N-杂环卡宾（NHC）铜（I）乙烯基的亲电子氟化导致氟烯烃的形成。炔烃可通过与原位生成的（NHC）铜（I）硼基反应，然后与N-氟苯磺酰亚胺（NFSI）反应而转化为顺式（β-氟乙烯基）硼酸酯。该顺序产生了来自末端炔烃的抗马尔科夫尼科夫氟化产物。顺式（β-氟乙烯基）三氟硼酸酯的氧化产生α-氟酮，而钯催化的Suzuki-Miyaura偶联产生四取代的单氟烯烃。
• Coupling of 2-Substituted 1-Fluorovinylstannanes with Organic Halides Catalyzed by Palladium(0)/Copper(I) Iodide. A Mild and Stereospecific Method to Monofluoroolefins
  作者：Chen、Keith Wilcoxen、Yun-Fei Zhu、Kyung-il Kim、James R. McCarthy

  DOI：10.1021/jo982200n

  日期：1999.5.1

  The palladium-catalyzed cross-coupling reactions of (E)- or (Z)-1-fluorovinylstannanes with aryl iodides and vinyl iodides provide good yields of stereoisomerically pure substituted fluoroolefins with retention of the double bond geometry. The reaction takes place with copper(I) iodide present as a cocatalyst at ambient temperature or in refluxing tetrahydrofuran and is tolerant of a variety of functional groups. Highly functionalized and stereoisomerically pure monofluorovinyl ketones also were obtained under mild conditions by the coupling of 1-fluorovinylstannanes with acid chlorides. (1)H-(19)F} NOE NMR experiments unequivocally established the stereochemistry of the coupling products E-14 and Z-14.
• Palladium/Copper (I) halide-cocatalyzed stereospecific coupling of 1-fluorovinylstannanes with aryl iodides and acyl chlorides
  作者：Chen Chen、Keith Wilcoxen、Kyung-il Kim、James R. McCarthy

  DOI：10.1016/s0040-4039(97)10003-x

  日期：1997.11

  Cross-coupling of 1-fluorovinylstannanes with aryl iodides or acyl chlorides, cocatalyzed by palladium and copper (I) iodide proceeded under mild conditions to give substituted fluoro olefins and alpha-fluoro-alpha,beta-unsaturated ketones, respectively, in good yields with retention of configuration. (C) 1997 Elsevier Science Ltd.
• 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.