(E)-(1-fluoro-2-methyl-2-phenylethenyl)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: (E)-(1-fluoro-2-methyl-2-phenylethenyl)benzene
• 英文别名: (E)-(1-fluoroprop-1-ene-1,2-diyl)dibenzene；(E)-1-fluoro-1,2-diphenylprop-1-ene；[(E)-1-fluoro-1-phenylprop-1-en-2-yl]benzene
• 化学式: C₁₅H₁₃F
• 分子量: 212.267
• InChiKey: ALDZLGXDNCOHFW-NTCAYCPXSA-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：

  二乙氧基磷酰-苯基-甲醇 在 二乙胺基三氟化硫 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 生成 (E)-(1-fluoro-2-methyl-2-phenylethenyl)benzene
  参考文献：
  名称：

  A General and Efficient Route for the Preparation of Phenyl-Substituted Vinyl Fluorides

  摘要：

  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.

  DOI：

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

文献信息

• Stereoselective synthesis of iodofluoroalkenes by iodofluorination of alkynes using IF5-pyridine-HF
  作者：Hitoshi Ukigai、Shoji Hara

  DOI：10.1016/j.tetlet.2016.02.063

  日期：2016.3

  The iodofluorination of alkynes was carried out using IF5-pyridine-HF and hydroquinone. The iodofluorination of an internal alkyne and a terminal alkyne proceeded stereoselectively to give the corresponding iodofluoroalkenes. An unsymmetrically substituted internal alkyne and electron deficient alkyne also afforded the corresponding iodofluoroalkenes stereoselectively. The iodofluoroalkenes thus obtained

  使用IF 5-吡啶-HF和对苯二酚进行炔烃的碘氟化。内部炔烃和末端炔烃的碘氟化立体选择性进行，得到相应的碘氟烯烃。不对称取代的内部炔烃和电子不足的炔烃还立体选择性地提供了相应的碘氟烯烃。由此获得的碘代氟代烯烃被用于二和三取代的氟代烯烃的立体选择性合成中。
• Controlled Single and Double Iodofluorination of Alkynes with DIH- and HF-Based Reagents
  作者：Lukas Pfeifer、Véronique Gouverneur

  DOI：10.1021/acs.orglett.8b00321

  日期：2018.3.16

  terminal alkynes using 1,3-diiodo-5,5,-dimethylhydantoin and HF-based reagents is disclosed. This approach is used to prepare a fluorinated tamoxifen derivative in two steps from commercially available starting materials. A facile method enabling controlled regioselective double iodofluorination of terminal alkynes is also presented.

  公开了使用1，3-二碘-5，5，-二甲基乙内酰脲和基于HF的试剂进行内部和末端炔的区域和立体选择性碘氟化的新方案。该方法用于从市售原料中分两步制备氟化他莫昔芬衍生物。还提出了一种可控制末端炔烃的区域选择性双碘氟化的简便方法。
• 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）。