(Z)-1-(2-fluorovinyl)naphthalene | 123133-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (Z)-1-(2-fluorovinyl)naphthalene
• 英文别名: 1-(2-fluorovinyl)naphthalene；1-[(Z)-2-fluoroethenyl]naphthalene
• CAS: 123133-14-2
• 化学式: C₁₂H₉F
• 分子量: 172.202
• InChiKey: GRIXOBHPFFEMLW-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  1
• 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：

  1-chloro-1-fluoro-2-(1-naphthyl)ethyl phenyl sulfoxide 在 copper(l) iodide 、 苯基溴化镁 作用下， 反应 1.0h， 以26%的产率得到(Z)-1-(2-fluorovinyl)naphthalene
  参考文献：
  名称：

  A Novel Generation and Behavior of Alkylfluorocarbenoids from α,α-Chlorofluoroalkyl Sulfoxides

  摘要：

  α,α-氯氟烷基硫醚与格氏试剂发生亲核脱硫反应，生成烷基氟碳化合物，在碘化铜（I）的存在下，烷基氟碳化合物塌缩成顺式氟烯烃。

  DOI：

  10.1246/cl.1989.309

文献信息

• A Simple, Two-Step, Site-Specific Preparation of Fluorinated Naphthalene and Phenanthrene Derivatives from Fluorobromo-Substituted Alkenes
  作者：Yi Wang、Jianjun Xu、Donald J. Burton

  DOI：10.1021/jo061305k

  日期：2006.9.1

  two-step procedure for the site-specific preparation of fluorinated naphthalene and phenanthrene derivatives is described. The Sonogashira reaction of bromofluoro-substituted alkenes with terminal alkynes, followed by base-catalyzed cyclization in refluxing N-methyl-2-pyrrolidinone (NMP), affords the corresponding fluorinated naphthalene and phenanthrene derivatives in good yields.

  描述了一种用于现场具体制备氟化萘和菲衍生物的简便的两步程序。溴氟取代的烯烃与末端炔烃的Sonogashira反应，然后在回流的N-甲基-2-吡咯烷酮（NMP）中进行碱催化的环化反应，以良好的收率得到相应的氟化萘和菲衍生物。
• Behaviors of α-Fluorocarbenoids Derived from the Nucleophilic Desulfinylation of α-Chloro-α-fluoroalkyl Sulfoxides
  作者：Hidemitsu Uno、Katsuji Sakamoto、Fumihiko Semba、Hitomi Suzuki

  DOI：10.1246/bcsj.65.210

  日期：1992.1

  2-Aryl-1-chloro-1-fluoroethyl sulfoxides underwent nucleophilic desulfinylation with PhMgBr to give (Z)-fluorostyrene derivatives in a very stereoselective manner (> 33 : 1) via an α-fluorocarbene species. When treated with 3 equiv of PhLi in the presence of N,N,N′,N′-tetramethylethylenediamine, they similarly formed fluorostyrenes as a stereoisomeric mixture (E : Z = 2 : 1), but with 1 equiv of PhLi 2-aryl-1-chloro-1-fluoroethanes were the major product. On the other hand, no formation of a fluoroalkene was observed in the desulfinylation of 1-chloro-1-fluoro-4-phenylbutyl sulfoxide with the nucleophiles. In the latter reaction, oxidation and/or phenylation of the intermediate carbene were the main pathways.

  2-芳基-1-氯-1-氟乙基亚砜与PhMgBr发生亲核去亚砜反应，以非常立体选择性的方式（> 33:1）生成（Z）氟苯乙烯衍生物，通过一个α-氟碳烯物种。当与3等物的PhLi在N,N,N′,N′-四甲基乙烯二胺存在下处理时，它们同样生成了氟苯乙烯的立体异构体混合物（E:Z = 2:1），但在1等物的PhLi下，2-芳基-1-氯-1-氟乙烷是主要产物。另一方面，在1-氯-1-氟-4-苯基丁基亚砜的去亚砜反应中，没有观察到氟烯烃的形成。在后者反应中，中间碳烯的氧化和/或苯基化是主要途径。
• Synthesis of monofluoroalkenes through selective hydrodefluorination of gem-difluoroalkenes with Red-Al®
  作者：Jingjing Wu、Juan Xiao、Wenpeng Dai、Song Cao

  DOI：10.1039/c5ra04221f

  日期：——

  A practical approach for the selective hydrodefluorination of gem-difluoroalkenes using Red-Al® as reductant at room temperature in CH₂Cl₂ was reported. Monofluoroalkenes were obtained in moderate to high yields with good E-selectivity.

  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。
• Electrocatalysis-Enabled Stereoselective Synthesis of Monofluoroalkenes via Hydrodefluorination of <i>gem</i>-Difluoroakenes
  作者：Xiaoying Wang、Jiaxi Cai、Haixia Song、Le Liu、Xin-Hua Duan、Mingyou Hu

  DOI：10.1021/acs.orglett.4c00112

  日期：2024.3.1

  We report a simple and economical method to synthesize monofluoroalkenes via the electrochemical hydrodefluorination of gem-difluoroalkenes. This reaction proceeds efficiently at room temperature, eliminating the requirement for a costly transition metal catalyst, ligand, and external reducing agent. The monofluoroalkene products can be obtained in medium to good yields and up to 99:1 E/Z selectivity

  我们报告了一种通过宝石二氟烯烃的电化学加氢脱氟合成单氟烯烃的简单且经济的方法。该反应在室温下有效进行，无需昂贵的过渡金属催化剂、配体和外部还原剂。单氟烯烃产品的产率中等至良好， E / Z选择性高达 99:1。该反应很容易扩展到克级。
• UNO, HIDEMITSU;SEMBA, FUMIHIKO;TASAKA, TADATAKA;SUZUKI, HITOMI, CHEM. LETT.,(1989) N, C. 309-312
  作者：UNO, HIDEMITSU、SEMBA, FUMIHIKO、TASAKA, TADATAKA、SUZUKI, HITOMI

  DOI：——

  日期：——