1,1-dibromo-2,2-bis(trifluoromethyl)-ethylene | 56152-73-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-dibromo-2,2-bis(trifluoromethyl)-ethylene
• 英文别名: 1,1-Dibromo-3,3,3-trifluoro-2-(trifluoromethyl)prop-1-ene
• CAS: 56152-73-9
• 化学式: C₄Br₂F₆
• 分子量: 321.842
• InChiKey: UTNZBQDJEJMRRT-UHFFFAOYSA-N

物化性质

• 沸点：
  176.7±40.0 °C(Predicted)
• 密度：
  2.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1-dibromo-2,2-bis(trifluoromethyl)-ethylene 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 perfluoro(t-butyl) caesium
  参考文献：
  名称：

  Fluorination Triggers Fluoroalkylation: Nucleophilic Perfluoro‐ tert ‐butylation with 1,1‐Dibromo‐2,2‐bis(trifluoromethyl)ethylene (DBBF) and CsF

  摘要：

  AbstractPerfluoro‐tert‐butylation reaction has long remained a challenging task. We now report the use of 1,1‐dibromo‐2,2‐bis(trifluoromethyl)ethylene (DBBF) as a practical reagent for perfluoro‐tert‐butylation reactions for the first time. Through a consecutive triple‐fluorination process with DBBF and CsF, the (CF3)3C− species can be liberated and observed, which is able to serve as a robust nucleophilic perfluoro‐tert‐butylating agent for various electrophiles. The power of this synthetic protocol is evidenced by the efficient synthesis of structurally diverse perfluoro‐tert‐butylated molecules. Multiple applications demonstrate the practicability of this method, as well as the superiority of perfluoro‐tert‐butylated compounds as sensitive probes. The perfluoro‐tert‐butylated product was successfully applied in 1H‐ and 19F‐magnetic resonance imaging (MRI) experiment with an ultra‐low field (ULF) MRI system.

  DOI：

  10.1002/anie.202113727
• 作为产物：
  描述：

  全氟异丁烯 在 吡啶 、 苯甲酰氯 作用下， 生成 1,1-dibromo-2,2-bis(trifluoromethyl)-ethylene
  参考文献：
  名称：

  Exchange of fluorine by chlorine in perfluoroisobutylene

  摘要：

  DOI：

  10.1007/bf00922961

文献信息

• Novel reactions of perfluoro-2-(trifluoromethyl)-propene
  作者：S. Munavalli、E.O. Lewis、A.J. Muller、D.I. Rossman、D.K. Rohrbaugh、C.P. Ferguson

  DOI：10.1016/s0022-1139(00)80569-2

  日期：1993.8

  hydrocarbon counterpart, perfluoro-2-(trifluoromethyl)propene is a highly reactive compound. It participates in both heterolytic and homolytic reactions. It readily reacts with nucleophiles and sluggishly with electrophiles. It reacts as well with common organic solvents, such as dimethylformamide, ethanol and others. In this communication, we describe its reactions with trifluoromethylthiocopper, sulfur

  与它的烃对应物不同，全氟-2-（三氟甲基）丙烯是高反应性化合物。它参与了杂溶和均溶反应。它容易与亲核试剂反应，而与亲电子试剂反应缓慢。它也可以与常见的有机溶剂（例如二甲基甲酰胺，乙醇等）反应。在本文中，我们描述了其与三氟甲基硫代铜，三氧化硫和三丁基氰化锡的反应，各种产物的形成机理及其质谱数据。
• Regioselective Aromatic Perfluoro-<i>tert</i>-butylation Using Perfluoro-<i>tert</i>-butyl Phenyl Sulfone and Arynes
  作者：Zhiqiang Wei、Lixian Wen、Kaidi Zhu、Qian Wang、Yanchuan Zhao、Jinbo Hu

  DOI：10.1021/jacs.2c10479

  日期：2022.12.7

  synthetic protocol to realize aromatic perfluoro-tert-butylation. The key to the success is the identification of PFtB phenyl sulfone as a new source of PFtB anion, which reacts with arynes in a highly regioselective manner to afford perfluoro-tert-butylated arenes in high yields. The application of the method is demonstrated by the preparation of sensitive 19F-labeled NMR probes with an extraordinary resolving

  长期以来，人们一直在寻求将全氟叔丁基（PFtB，CF 3基团的较大类似物）选择性引入芳烃中，但仍然是一项艰巨的任务。我们在此报告了第一个实现芳香族全氟叔丁基化的通用合成方案。成功的关键是将 PFtB 苯基砜鉴定为 PFtB 阴离子的新来源，它以高度区域选择性的方式与芳烃反应，以高产率提供全氟叔丁基芳烃。该方法的应用通过制备具有非凡分辨能力的灵敏的19 F-标记的NMR探针来证明。
• 一种含氟叔碳中心的构建方法
  申请人：中国科学院上海有机化学研究所

  公开号：CN114956951A

  公开（公告）日：2022-08-30

  本发明提供了一种以含氟烯烃为原料，构建含氟叔碳中心的方法。具体地，本发明提供了一种如下式I所示的化合物的用途；其中，各基团的定义如说明书中所述。所述式I化合物可以用作为含氟叔碳负离子的前体，用于常见亲电试剂的氟烷基化反应。本方法反应条件温和，操作简便，成本低，底物官能团兼容性好，易于放大，分离，具有工业化生产的应用前景。
• Morken; Bachand, Patrick C.; Swenson, Dale C., Journal of the American Chemical Society, 1993, vol. 115, # 13, p. 5430 - 5439
  作者：Morken、Bachand, Patrick C.、Swenson, Dale C.、Burton, Donald J.

  DOI：——

  日期：——
• Fluorination Triggers Fluoroalkylation: Nucleophilic Perfluoro‐ <i>tert</i> ‐butylation with 1,1‐Dibromo‐2,2‐bis(trifluoromethyl)ethylene (DBBF) and CsF
  作者：Qian Wang、Quan Tao、Hui Dong、Chuanfa Ni、Xiaoming Xie、Jinbo Hu

  DOI：10.1002/anie.202113727

  日期：2021.12.20

  AbstractPerfluoro‐tert‐butylation reaction has long remained a challenging task. We now report the use of 1,1‐dibromo‐2,2‐bis(trifluoromethyl)ethylene (DBBF) as a practical reagent for perfluoro‐tert‐butylation reactions for the first time. Through a consecutive triple‐fluorination process with DBBF and CsF, the (CF3)3C− species can be liberated and observed, which is able to serve as a robust nucleophilic perfluoro‐tert‐butylating agent for various electrophiles. The power of this synthetic protocol is evidenced by the efficient synthesis of structurally diverse perfluoro‐tert‐butylated molecules. Multiple applications demonstrate the practicability of this method, as well as the superiority of perfluoro‐tert‐butylated compounds as sensitive probes. The perfluoro‐tert‐butylated product was successfully applied in 1H‐ and 19F‐magnetic resonance imaging (MRI) experiment with an ultra‐low field (ULF) MRI system.