1-氟环戊烯 | 27415-42-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 中文名称: 1-氟环戊烯
• 英文名称: 1-fluorocyclopent-1-ene
• 英文别名: 1-fluorocyclopentene
• CAS: 27415-42-5
• 化学式: C₅H₇F
• 分子量: 86.109
• InChiKey: IFRIJEKNVVMZBB-UHFFFAOYSA-N

物化性质

• 沸点：
  64.9±19.0 °C(Predicted)
• 密度：
  0.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  1,1-二氟环戊烷 在 aluminum oxide 作用下， 生成 1-氟环戊烯
  参考文献：
  名称：

  Synthesis of 1-fluorocycloalkenes

  摘要：

  DOI：

  10.1021/jo00805a019

文献信息

• Carbon−Carbon Coupling of C(sp³)−F Bonds Using Alumenium Catalysis
  作者：Weixing Gu、Mason R. Haneline、Christos Douvris、Oleg V. Ozerov

  DOI：10.1021/ja903927c

  日期：2009.8.12

  alkylation of aliphatic C-F bonds (alkylative defluorination or AlkDF) by alkylaluminum compounds. Only C(sp(3))-F bonds undergo AlkDF; C(sp(2))-F bonds are unaffected. Examples of compounds undergoing AlkDF include monofluoroalkanes, gem-difluorocyclopentane, and compounds containing a CF(3) group attached to either an aryl or an alkyl substituent. Conversion of C-F bonds to C-Me bonds is accomplished with

  与六溴碳硼烷阴离子偶联的二烷基铝阳离子等价物可用作烷基铝化合物对脂肪族 CF 键（烷基化脱氟或 AlkDF）进行烷基化的有效且长寿命的催化剂。只有 C(sp(3))-F 键经历 AlkDF；C(sp(2))-F 键不受影响。经历 AlkDF 的化合物的例子包括单氟烷烃、嵴二氟环戊烷和含有连接到芳基或烷基取代基的 CF(3) 基团的化合物。CF 键到 C-Me 键的转换是使用 Me(3)Al 作为化学计量试剂以高保真度完成的。在与 Et(3)Al 的反应中，CF 键的加氢脱氟与烷基化竞争，这可能表明竞争性氢化物与来自 Et(3)Al 的烷基转移。在三烷基铝试剂中，1.1-1。每个 Al 有 4 个烷基可用于替换 CF 键。有机铝化合物可有效去除反应混合物中的水分，无需使用严格干燥的溶剂。一些有机铝化合物，尤其是甲基铝氧烷，能够使 AlkDF 与更多反应性底物发生反应，但铝的催化在提高速率和在某些情况下显着提高选择性方面比未催化的
• Facile Generation of a Strained Cyclic Vinyl Cation by Thermal Solvolysis of Cyclopent-1-enyl-λ³-bromanes
  作者：Kazunori Miyamoto、Motoo Shiro、Masahito Ochiai

  DOI：10.1002/anie.200903368

  日期：2009.11.9

  Last of the cyclic vinyl cations: The simple solvolysis of cyclopent‐1‐enyl‐λ3‐bromane efficiently generates the highly strained cyclopent‐1‐enyl cation at room temperature (see scheme). The very high nucleofugality of the aryl‐λ3‐bromanyl groups are responsible for this unique unimolecular dissociation.

  最后环状乙烯阳离子：的简单溶剂分解环戊-1-烯基- λ 3 -bromane有效地产生在室温下高应变环戊-1-烯基阳离子（参见方案）。芳基- λ的非常高的nucleofugality 3 -bromanyl组负责这种独特的单分子离解。
• An Experimental and Computational Investigation of the Electrocyclic Ring Opening of α-Fluorocyclopropyl Radicals
  作者：Christopher J. LaFrancois、Philip B. Shevlin

  DOI：10.1016/s0040-4020(97)00348-7

  日期：1997.7

  A series of α-fluorobicyclopropyl radicals were generated by the reaction of CF with the corresponding cycloalkene. The tendency of these radicals to undergo electrocyclic ring opening to the corresponding cyclic allyl radicals was evaluated computationally and experimentally. The symmetry forbidden ring openings will occur if there is significant thermodynamic driving force. AM1 calculations and product

  CF与相应的环烯烃反应生成了一系列α-氟二环丙基。通过计算和实验评估了这些自由基与相应的环状烯丙基自由基发生开环的趋势。如果存在很大的热力学驱动力，则会出现对称的禁止环开口。AM1的计算和产物分析表明，那些开环放热度的计算值为50 kcal / mol或更高的自由基会提供开环产物©1997 Elsevier Science Ltd.。
• Kinetics of alkylhalocarbene rearrangements: modulation by fluorine substituents
  作者：Robert A. Moss、Guo Jie Ho、Weiguo Liu

  DOI：10.1021/ja00029a025

  日期：1992.1

  Rate constants were measured by laser flash photolytic methods for hydrogen and carbon 1,2-migrations in four different alkylchlorocarbenes and in the analogous alkylfluorocarbenes. The carbenes, products, and rate constants (s-1) were as follows: phenoxymethylchlorocarbene to (Z)- and (E)-1-chloro-2-phenoxyethene (Z/E approximately 4/1), k = 3.6 x 10(7); phenoxymethylfluorocarbene to (Z)-1-fluoro-2-phenoxyethene (Z/E > 10/1), k = 1.3 x 10(7); neopentylchlorocarbene to (Z)- and (E)-1-tert-butyl-2-chloroethene (Z/E = 1/12), k = 1.4 x 10(7); neopentylfluorocarbene to (Z)- and (E)-1-tert-butyl-2-fluoroethene (Z/E = 1/2.5), k = 2.6 X 10(6); cyclobutylchlorocarbene to 1-chlorocyclopentene (C migration) and chloromethylenecyclobutane (H migration), k(c) = 4.6 X 10(7), k(H) = 2.1 X 10(7); cyclobutylfluorocarbene to 1-fluorocyclopentene (C migration) and fluoromethylenecyclobutane (H migration), k(c) = 1.8 x 10(6), k(H) = 5.3 x 10(5); cyclopropylchlorocarbene to 1-chlorocyclobutene, k = 9 x 10(5); cyclopropylfluorocarbene to 1-fluorocyclobutene, k = 1.4 x 10(5). Activation energies for several of these processes were in the range of 2-4 kcal/mol, with A approximately 10(8)-10(9) s-1.
• Synthesis of 1-fluorocycloalkenes
  作者：Donald R. Strobach、G. A. Boswell

  DOI：10.1021/jo00805a019

  日期：1971.3