(E)-1-Fluoro-2-(3,4-methylenedioxyphenyl)ethylene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (E)-1-Fluoro-2-(3,4-methylenedioxyphenyl)ethylene
• 英文别名: 5-(2-fluorovinyl)benzo[1,3]dioxole；5-[(E)-2-fluoroethenyl]-1,3-benzodioxole
• 化学式: C₉H₇FO₂
• 分子量: 166.152
• InChiKey: SMBCCDKALQDIHG-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-(2,2-difluorovinyl)benzo[d][1,3]dioxole 在 红铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到
  参考文献：
  名称：

  Synthesis of monofluoroalkenes through selective hydrodefluorination of gem-difluoroalkenes with Red-Al®

  摘要：

  报道了一种在室温下使用Red-Al®作为还原剂，在CH₂Cl₂中选择性地进行gem-二氟烯烃的水氢脱氟反应的实用方法。得到了中等到高产率的单氟烯烃，并具有良好的E-选择性。

  DOI：

  10.1039/c5ra04221f

文献信息

• Generation of Acetylides by Treatment of Fluoroethylenes with LDA: Preparation of Propargyl Alcohols
  作者：Kentaro Kataoka、Sadao Tsuboi

  DOI：10.1055/s-2000-6336

  日期：——

  The fluoroethylenes 3 produced the corresponding acetylides via dehydrofluorination and deprotonation by treatment with 2 equivalents of LDA in THF at 0 °C. These acetylides reacted with aldehydes and ketones to afford propargyl alcohols in good yields.

  氟乙烯 3 通过脱氢氟化和去质子化，在 0 °C 的四氢呋喃溶液中用 2 个等量的 LDA 处理，生成相应的乙酰化物。这些乙酰化物与醛和酮反应生成丙炔醇，收率很高。
• 1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F): a versatile fluoromethylidene synthon and its use in the synthesis of monofluorinated alkenes via Julia–Kocienski olefination
  作者：Lingui Zhu、Chuanfa Ni、Yanchuan Zhao、Jinbo Hu

  DOI：10.1016/j.tet.2010.04.113

  日期：2010.7

  1-tert-Butyl-1H-tetrazol-5-yl fluoromethyl sulfone (TBTSO2CH2F) has been developed as a new and efficient fluoromethylidene synthon for the synthesis of both terminal and internal monofluoroalkenes via Julia-Kocienski olefination reaction. The base-mediated reaction between TBTSO2CH2F and carbonyl compounds (aldehydes and ketones) provided terminal monofluoroalkenes in good yields with moderate E/Z selectivity. The dominance of E- or Z-fluoroalkenes could be controlled by selection of proper reaction solvent and temperature. TBTSO2CH2F reagent was also found to be readily a-alkylated, acylated, and phenylsulfonylated to give corresponding alpha-functionalized fluorosulfones, which could be used in the synthesis of alkyl-, acyl-, and phenylsulfonyl-substituted internal monofluoroalkenes via Julia-Kocienski olefination reactions. (C) 2010 Elsevier Ltd. All rights reserved.