4-tert-butyl-1-fluorocyclohexene

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 4-tert-butyl-1-fluorocyclohexene
• 英文别名: 1-t-butyl-4-fluoro-3-cyclohexene；4-t-Butyl-1-fluorocyclohexene
• 化学式: C₁₀H₁₇F
• 分子量: 156.243
• InChiKey: HEEYIVLNCUYENJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-1-fluorocyclohexene 在 Sm(HMDS)₂ 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以55%的产率得到4-(叔丁基)-1-环己烯
  参考文献：
  名称：

  Solvent dependent reductive defluorination of aliphatic C–F bonds employing Sm(HMDS)2

  摘要：

  在正己烷中，Sm(HMDS)2能高效地催化一级、二级和三级烷基氟化物的快速断裂，产率良好至极佳。与使用四氢呋喃作为溶剂相比，Sm(HMDS)2在正己烷中对C-F键的还原能力表现出独特的增强效果。

  DOI：

  10.1039/c3cc37828d
• 作为产物：
  描述：

  4-叔丁基环己酮 在 二乙胺基三氟化硫 、 aluminum oxide 作用下， 生成 4-tert-butyl-1-fluorocyclohexene
  参考文献：
  名称：

  Effects of Complexation with 18-Crown-6 on the Hypernucleofugality of Phenyl-λ³-iodanyl Groups. Synthesis of Vinyl-λ³-iodane·18-Crown-6 Complex

  摘要：

  4-tert-Butyl-1-cyclohexenyl(phenyl)(tetrafluoroborato)-lambda(3)-iodane forms a discrete supramolecular complex by the reaction with 18-crown-6. Solvolysis of the cyclohexenyl-lambda(3)-iodane in the presence of 18-crown-6 indicates that the complexation with 18-crown-6 tends to decrease the leaving group ability of hypervalent phenyl-lambda(3)-iodanyl groups.

  DOI：

  10.1021/ol050858z

文献信息

• Fluorination with aminosulfur trifluorides
  申请人：Air Products and Chemicals, Inc.

  公开号：US06080886A1

  公开（公告）日：2000-06-27

  A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.

  使用二芳基、二烷氧基烷基、烷基烷氧基烷基、芳基烷氧基烷基和环氨基硫三氟化物氟化试剂对氧和卤原子位点进行氟化的一种氟化方法被披露。
• Process for producing alpha, alpha-difluorocycloalkane compound
  申请人：——

  公开号：US20030078460A1

  公开（公告）日：2003-04-24

  A method for producing an &agr;,&agr;-difluorocycloalkane at high purity with good efficiency, which comprises a step of treating a fluorocycloalkene with hydrogen fluoride wherein the fluorocycloalkene has one fluorine atom directly bonded to a carbon atom of carbon-carbon unsaturated double bond, more preferably, a step of directly adding the hydrogen fluoride to a reaction mixture obtained by treating the cycloalkanone with the de-oxygen fluorinating agent.

  一种用高纯度和良好效率生产α，α-二氟环烷烃的方法，包括处理氟环烷烯与氢氟酸的步骤，其中氟环烷烯的一个氟原子直接连接到碳-碳不饱和双键的碳原子，更优选地，直接将氢氟酸添加到通过用脱氧氟化剂处理环戊酮得到的反应混合物的步骤。
• Thermally stable aminosulfur trifluorides
  申请人：Air Products and Chemicals, Inc.

  公开号：US06207860B1

  公开（公告）日：2001-03-27

  Diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating agents are disclosed.

  已披露了Diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl-和环状氨硫三氟化物氟化试剂。
• Reaction of Chlorosulfonyl Isocyanate with Fluorosubstituted Alkenes: Evidence of a Concerted Pathway
  作者：Dale F. Shellhamer、Kevyn J. Davenport、Danielle M. Hassler、Kelli R. Hickle、Jacob J. Thorpe、David J. Vandenbroek、Victor L. Heasley、Jerry A. Boatz、Arnold L. Reingold、Curtis E. Moore

  DOI：10.1021/jo101240s

  日期：2010.11.19

  Concerted reactions are indicated for the electrophilic addition of chlorosulfonyl isocyanate with monofluoroalkenes. A vinyl fluorine atom on an alkene raises the energy of a stepwise transition state more than the energy of the competing concerted pathway. This energy shift induces CSI to react with monofluoroalkenes by a one-step process. The low reactivity of CSI with monofluoroalkenes, stereospecific

  对于氯磺酰基异氰酸酯与一氟烯烃的亲电子加成反应，表明了一致的反应。烯烃上的乙烯基氟原子比竞争性一致途径的能量更多地提高了逐步过渡态的能量。这种能量转移促使CSI通过一步过程与单氟烯烃反应。CSI与单氟烯烃的低反应性，立体定向反应，与纯氟烯烃的2：1尿嘧啶产物的不存在以及量子化学计算均支持协调一致的途径。
• Aminodifluorosulfinium Salts: Selective Fluorination Reagents with Enhanced Thermal Stability and Ease of Handling^,
  作者：Alexandre L’Heureux、Francis Beaulieu、Christopher Bennett、David R. Bill、Simon Clayton、François LaFlamme、Mahmoud Mirmehrabi、Sam Tadayon、David Tovell、Michel Couturier

  DOI：10.1021/jo100504x

  日期：2010.5.21

  Diethylaminodifluorosulfinium tetrafluoroborate (XtalFluor-E) and morpholinodifluorosulfinium tetrafluoroborate (XtalFluor-M) are crystalline fluorinating agents that are more easily handled and significantly more stable than Deoxo-Fluor, DAST, and their analogues. These reagents can be prepared in a safer and more cost-efficient manner by avoiding the laborious and hazardous distillation of dialkylaminosulfur trifluorides. Unlike DAST, Deoxo-Fluor, and Fluolead, XtalFluor reagents do not generate highly corrosive free-H F and therefore can be used in standard borosilicate vessels. When used in conjunction with promoters such as Et3N center dot 3HF, Et3N center dot 2HF, or DBU, XtalFluor reagents effectively convert alcohols to alkyl fluorides and carbonyls to gem-difluorides. These reagents are typically more selective than DAST and Deoxo-Fluor and exhibit superior performance by providing significantly less elimination side products.