(4,4-difluoro-3-methyl-3-buten-1-yl)benzene | 149683-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4,4-difluoro-3-methyl-3-buten-1-yl)benzene
• 英文别名: (4,4-difluoro-3-methylbut-3-enyl)benzene
• CAS: 149683-62-5
• 化学式: C₁₁H₁₂F₂
• 分子量: 182.213
• InChiKey: OLOBXQQJUNRSRX-UHFFFAOYSA-N

物化性质

• 沸点：
  202.7±40.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二[三氟甲基]汞 、 (4,4-difluoro-3-methyl-3-buten-1-yl)benzene 在 三苯基膦 、 sodium iodide 作用下， 以 四氢呋喃 为溶剂， 生成 1,1,2,2-tetrafluoro-3-(2-phenylethyl)-3-methylcyclopropane
  参考文献：
  名称：

  New Methodology for the Deoxygenative Difluoromethylenation of Aldehydes and Ketones; Unexpected Formation of Tetrafluorocyclopropanes

  摘要：

  [GRAPHICS]Generation of difluoromethylene phosphorus ylides in the presence of aldehydes and ketones results in Wittig-type reactions to give gem-difluoroalkenes, Subsequent in situ addition of difluorocarbene (carbenoid) can occur (increased with triphenylphosphine and decreased with tributylphosphine) to give tetrafluorocyclopropanes.

  DOI：

  10.1021/ol047416s
• 作为产物：
  描述：

  锡烷,三丁基[(1E)-1-氟-2-甲基-4-苯基-1-丁烯基]- 在 Selectfluor 作用下， 以 乙腈 为溶剂， 以35%的产率得到(4,4-difluoro-3-methyl-3-buten-1-yl)benzene
  参考文献：
  名称：

  乙烯基锡烷的亲电氟化的新方法。

  摘要：

  已开发出一种使用市售的1-氯甲基-4-氟-1,4-二氮杂双环[2.2.2]辛烷双-（四氟硼酸酯）（1）进行乙烯基锡烷的亲电氟化的新方法。

  DOI：

  10.1016/s0040-4039(00)93378-1

文献信息

• Difluoromethyl 2-Pyridyl Sulfone: A New <i>gem-</i>Difluoroolefination Reagent for Aldehydes and Ketones
  作者：Yanchuan Zhao、Weizhou Huang、Lingui Zhu、Jinbo Hu

  DOI：10.1021/ol100090r

  日期：2010.4.2

  Difluoromethyl 2-pyridyl sulfone, a previously unknown compound, was found to act as a novel and efficient gem-difluoroolefination reagent for both aldehydes and ketones. It was found that the fluorinated sulfinate intermediate in the reaction is relatively stable, which can be observed by 19F NMR and trapped with CH3I.

  发现二氟甲基2-吡啶基砜（一种以前未知的化合物）可同时作为醛和酮的新型高效二氟烯烃聚合试剂。发现反应中的氟化亚磺酸盐中间体相对稳定，这可以通过19 F NMR观察到并被CH 3 I捕获。
• Unusual Single Electron Transfer Reactions between Alkenes and Iodine Electrophiles^†
  作者：Zhengzhao Lou、Jingyu Hu、Chuanfa Ni、Xiu Wang、Jinbo Hu

  DOI：10.1002/cjoc.202300611

  日期：2024.3

  electron transfer (SET) process occurs between these two reactants by forming an electron-donor acceptor complex. Not only does this unusual single electron transfer reaction between an alkene and NIS add fundamentally important knowledge to organic chemistry, it also provides a valuable synthetic method as the new SET reaction mode with opposite regioselectivity as compared with the traditional ionic mode

  烯烃与亲电子试剂的亲电加成已在有机合成中得到广泛研究和应用。有机化学教科书将烯烃和碘亲电试剂（例如元素碘和N-碘代琥珀酰亚胺（NIS））之间的经典反应描述为典型的离子反应，其中形成碘鎓离子，然后受到亲核试剂的攻击。然而，在本文中，我们报告了烯烃和 NIS 之间一种新的、不寻常的反应模式；也就是说，通过形成电子供体受体复合物，在这两种反应物之间发生单电子转移（SET）过程。烯烃和NIS之间这种不寻常的单电子转移反应不仅为有机化学增添了极其重要的知识，而且还提供了一种有价值的合成方法，作为与传统离子模式相比具有相反区域选择性的新SET反应模式。
• Development of (Trifluoromethyl)zinc Reagent as Trifluoromethyl Anion and Difluorocarbene Sources
  作者：Kohsuke Aikawa、Wataru Toya、Yuzo Nakamura、Koichi Mikami

  DOI：10.1021/acs.orglett.5b02439

  日期：2015.10.16

  The trifluoromethylation of carbonyl compounds is accomplished by the stable (trifluoromethyOzinc reagent generated and then isolated from CF3I and ZnEt2, which can be utilized as a trifluoromethyl anion source (CF3-). The reaction proceeds smoothly with diamine as a ligand and ammonium salt as an initiator, providing the corresponding trifluoromethylated alcohol products. Moreover, the (trifluoromethyl)zinc reagent can also be employed as a difluorocarbene source (:CF2) not only for gem-difluoroolefination of carbonyl compounds with phosphine but also for gem-difluorocyclization of alkenes or alkynes via the thermal decomposition, respectively.
• New Methodology for the Deoxygenative Difluoromethylenation of Aldehydes and Ketones; Unexpected Formation of Tetrafluorocyclopropanes
  作者：Ireneusz Nowak、Morris J. Robins

  DOI：10.1021/ol047416s

  日期：2005.2.1

  [GRAPHICS]Generation of difluoromethylene phosphorus ylides in the presence of aldehydes and ketones results in Wittig-type reactions to give gem-difluoroalkenes, Subsequent in situ addition of difluorocarbene (carbenoid) can occur (increased with triphenylphosphine and decreased with tributylphosphine) to give tetrafluorocyclopropanes.
• A new method for the electrophilic fluorination of vinyl stannanes.
  作者：Donald P. Matthews、Shawn C. Miller、Esa T. Jarvi、Jeffrey S. Sabol、James R. McCarthy

  DOI：10.1016/s0040-4039(00)93378-1

  日期：1993.5

  A new method for the electrophilic fluorination of vinyl stannanes using commercially available 1-chloromethyl-4-fluoro-1,4- diazoniabicyclo[2.2.2]octane bis-(tetrafluoroborate) (1) has been developed.

  已开发出一种使用市售的1-氯甲基-4-氟-1,4-二氮杂双环[2.2.2]辛烷双-（四氟硼酸酯）（1）进行乙烯基锡烷的亲电氟化的新方法。