1,1-difluoro-2-methyl-2-(p-chlorophenyl)cyclopropane

• 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: 1,1-difluoro-2-methyl-2-(p-chlorophenyl)cyclopropane
• 英文别名: 1-chloro-4-(2,2-difluoro-1-methylcyclopropyl)benzene；1,1-Difluoro-2-(4-chlorophenyl)-2-methylcyclopropane
• 化学式: C₁₀H₉ClF₂
• 分子量: 202.631
• InChiKey: PXOBPSLUVGQSOY-UHFFFAOYSA-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：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对氯甲基苯乙烯 、 sodium 2,2,2-trifluoroacetate 在 偶氮二异丁腈 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以93%的产率得到1,1-difluoro-2-methyl-2-(p-chlorophenyl)cyclopropane
  参考文献：
  名称：

  Sodium Trifluoroacetate: an Efficient Difluorocarbene Precursor for Alkenes

  摘要：

  获得了一种新颖且高效的二氟卡宾前体。在简便的操作中，使用偶氮二异丁腈（AIBN）作为催化剂，多种烯烃可以与三氟乙酸钠进行顺式二氟环丙烷化反应，得到中等到高产率的相应产物。

  DOI：

  10.1246/cl.2005.1440

文献信息

• Trimethylsilyl fluorosulfonyldifluoroacetate (TFDA): a new, highly efficient difluorocarbene reagent
  作者：William R Dolbier、Feng Tian、Jian-Xin Duan、An-Rong Li、Samia Ait-Mohand、Olivia Bautista、Saiwan Buathong、J Marshall Baker、Jen Crawford、Pauline Anselme、Xiao Hong Cai、Aneta Modzelewska、Henryk Koroniak、Merle A Battiste、Qing-Yun Chen

  DOI：10.1016/j.jfluchem.2003.12.002

  日期：2004.3

  TFDA is readily prepared from the reaction of fluorosulfonyldifluoroacetic acid with trimethylsilyl chloride, and it is a very effective and efficient source of difluorocarbene for use in addition reactions to alkenes of a broad scope of reactivities. Acid-sensitive substrates may require an additional purification step involving treatment of the distilled TFDA with sufficient Et3N to remove the acid

  TFDA很容易从氟磺酰基二氟乙酸与三甲基甲硅烷基氯的反应中制备，它是非常有效的二氟卡宾来源，可用于与反应性范围很广的烯烃加成反应。对酸敏感的底物可能需要额外的纯化步骤，包括用足够的Et 3 N处理蒸馏过的TFDA以除去酸杂质。还可以制备其他三烷基甲硅烷基氟磺酰基二氟乙酸酯，并且发现它们具有类似于TFDA的反应性。三乙基衍生物TEFDA更易于以纯净状态制备，并且具有与TFDA相似的反应性。因此，它可能被证明是一种优良的试剂。
• METHOD FOR PRODUCING DIFLUOROCYCLOPROPANE COMPOUND
  申请人：Amii Hideki

  公开号：US20120277458A1

  公开（公告）日：2012-11-01

  Provided is a method for producing a difluorocyclopropane compound under milder reaction conditions and with high selectivity and high yield. The method for producing a difluorocyclopropane compound of the present invention is characterized by using sodium bromodifluoroacetate as a difluorocyclopropanation agent. With the disclosed method, a difluorocyclopropane compound can be produced under milder reaction conditions and with a higher conversion rate and a higher yield compared to conventional art. Further, by-products can be reduced significantly, thus allowing waste to be greatly reduced. Accordingly, the production method of the present invention is easy to implement industrially (can be employed on an industrial scale) and is thus extremely practical and useful.

  提供了一种在较温和的反应条件下、具有高选择性和高产率的制备二氟环丙烷化合物的方法。本发明的制备二氟环丙烷化合物的方法的特点是使用溴二氟乙酸钠作为二氟环丙烷化试剂。通过所披露的方法，与传统技术相比，可以在较温和的反应条件下生产二氟环丙烷化合物，并且具有更高的转化率和更高的产率。此外，副产物可以显著减少，从而大大减少废物。因此，本发明的生产方法易于在工业上实施（可在工业规模上应用），因此极其实用和有用。
• Sodium Bromodifluoroacetate: A Difluorocarbene Source for the Synthesis of gem-Difluorocyclopropanes
  作者：Hideki Amii、Kojun Oshiro、Yoshimichi Morimoto

  DOI：10.1055/s-0029-1218754

  日期：2010.6

  As a new difluorocarbene source, sodium bromodifluoroacetate (BrCF2CO2Na) was found to be effective for high-yielding­ synthesis of gem-difluorocyclopropanes and gem-difluorocyclopropenes under mild conditions. fluorine - carbenes - cycloaddition - cyclopropanes - cyclopropenes­

  发现溴二氟乙酸钠（BrCF 2 CO 2 Na）作为一种新的二氟卡宾来源，可在温和条件下有效地高产合成宝石-二氟环丙烷和宝石-二氟环丙烯。 氟-卡宾-环加成-环丙烷-环丙烯
• PROCESS FOR PRODUCING DIFLUOROCYCLOPROPANE COMPOUND
  申请人：Central Glass Company, Limited

  公开号：EP2522648A1

  公开（公告）日：2012-11-14

  Provided is a method for producing a difluorocyclopropane compound under milder reaction conditions and with high selectivity and high yield. The method for producing a difluorocyclopropane compound of the present invention is characterized by using sodium bromodifluoroacetate as a difluorocyclopropanation agent. With the disclosed method, a difluorocyclopropane compound can be produced under milder reaction conditions and with a higher conversion rate and a higher yield compared to conventional art. Further, by-products can be reduced significantly, thus allowing waste to be greatly reduced. Accordingly, the production method of the present invention is easy to implement industrially (can be employed on an industrial scale) and is thus extremely practical and useful.

  本发明提供了一种在较温和的反应条件下，以高选择性和高产率生产二氟环丙烷化合物的方法。本发明生产二氟环丙烷化合物的方法的特点是使用溴二氟乙酸钠作为二氟环丙烷化剂。与传统技术相比，本发明方法可以在更温和的反应条件下生产二氟环丙烷化合物，并具有更高的转化率和收率。此外，副产物也可显著减少，从而大大减少废物。因此，本发明的生产方法易于在工业上实施（可在工业规模上采用），因而非常实用和有用。
• An Improved Method for Difluorocyclopropanation of Alkenes
  作者：Joseph Sweeney、Duncan Gill、Neil McLay、Michael Waring、Christopher Wilkinson

  DOI：10.1055/s-0033-1341155

  日期：——

  Difluorocyclopropanation of alkenes using fluorinated acetate salts using convential heating is often a slow, inefficient, and energy-intensive process. We report here a modified protocol which enables the rapid (<5 min) preparation of 1,1-difluorocyclopropanes, using microwave irradiation. The new procedure is not only considerably faster than previously reported methods, but it also employs easily removed, low boiling-point solvents and avoids the use of highly toxic or ozone-depleting substances.