N,N-dimethyl-4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)benzeneamine | 80791-09-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)benzeneamine
• 英文别名: 4-perfluorooctyl-N,N-dimethylaniline；Benzenamine, 4-(heptadecafluorooctyl)-N,N-dimethyl-；4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)-N,N-dimethylaniline
• CAS: 80791-09-9
• 化学式: C₁₆H₁₀F₁₇N
• 分子量: 539.235
• InChiKey: CSDRFIOFQKNRSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为产物：
  描述：

  全氟辛基碘烷 、 N,N-二甲基苯胺 以 水 为溶剂， 反应 4.0h， 以86%的产率得到N,N-dimethyl-4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)benzeneamine
  参考文献：
  名称：

  在水和水性介质中用全氟烷基对富电子芳烃进行多相光诱导均裂芳烃取代 - 自由基离子反应

  摘要：

  富电子芳香核与全氟烷基 Rf 基团的光诱导电子转移 (PET) 取代反应在水或水性混合物中进行，以良好的产率 (57-88%) 提供由 Rf 部分取代芳香族 H 原子产生的取代产物）。讨论了一些机理方面，支持 PET 反应的概念，导致经典的自由基均裂芳烃取代 (HAS)，然后是电子转移 (ET)，然后是质子转移 (PT) 序列。提出了一种叠加在氧化还原过程上的自由基机制来解释产品的形成。

  DOI：

  10.1002/ejoc.201201271

文献信息

• Nickel(0)-Catalyzed Fluoroalkylation of Alkenes, Alkynes, and Aromatics with Perfluoroalkyl Chlorides
  作者：Xiao-Ting Huang、Qing-Yun Chen

  DOI：10.1021/jo010178j

  日期：2001.6.1

  Treatment of perfluoroalkyl chlorides (R(F)Cl) with alkenes, alkynes, or aromatics in the presence of 0.1 equiv of nickel dichloride, 1.5 equiv of zinc powder, and 0.4 equiv of triphenylphosphine in DMF at 95-100 degrees C for 6-8 h give the corresponding perfluoroalkylated products in good yields. A single electron-transfer mechanism is suggested.

  在95至100摄氏度的DMF中，在0.1当量的二氯化镍，1.5当量的锌粉和0.4当量的三苯膦存在下，用烯烃，炔烃或芳烃处理全氟烷基氯化物（R（F）Cl），在6-100 8小时以良好的产率得到相应的全氟烷基化产物。提出了单电子转移机理。
• PERFLUOROALKYLATION OF AROMATIC COMPOUNDS WITH R_fI(Ph)OSO₂CF₃
  作者：Teruo Umemoto、Yuriko Kuriu、Hideo Shuyama

  DOI：10.1246/cl.1981.1663

  日期：1981.12.5

  Perfluoroalkylation of various aromatic compounds with perfluoroalkylphenyliodonium trifluoromethanesulfonate (FITS) under mild conditions was described. The reactivity of other perfluoroalkyliodonium salts was also examined.

  描述了在温和条件下用全氟烷基苯基碘鎓三氟甲磺酸盐 (FITS) 对各种芳族化合物进行全氟烷基化。还检查了其他全氟烷基碘盐的反应性。
• Method for producing coupling compound
  申请人：Sumitomo Chemical Company, Limited

  公开号：US20040161404A1

  公开（公告）日：2004-08-19

  There are disclosed a method for producing a cross-coupling compound of formula (3): (Y—) (n−1) R 1 —R 2 —(R 1 ) (n′−1) (3) wherein R 1 represents a substituted or unsubstituted, linear, branched, or cyclic hydrocarbon group, and n and n′ each represent 1 or 2, provided that when n and n′ are the same, both n and n′ are not 2, R 2 represents a substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl or substituted or unsubstituted alkenyl group, and Y represents R 2 or X 1 , wherein R 2 is as defined above, and X 1 represents a chlorine, bromine or iodine atom, which method comprises reacting an organic halide of formula (1): n′(R 1 X l n ), wherein R 1 is as defined above and carbon atoms at the &agr; and &bgr; positions relative to X 1 are sp 3 carbon atoms, and X 1 , n and n′ are as defined above, with a boron compound of formula (2): m{R 2 (BX 2 2 ) n′ }, wherein R 2 and n′ are as defined above, X 2 independently represents a hydroxyl group or an alkoxy or aryloxy group, or X 2 2 together form an alkoxy or aryloxy group, and m represents 1 or 2, and m≧n, and the boron atom is bonded with a sp 2 carbon atom of R 2 group, or a boronic acid trimer anhydride thereof, in the presence of a base and a catalyst comprising a nickel compound and a compound of formula (i): 1 wherein R 3 represents a substituted or unsubstituted alkyl group, R 4 represents a hydrogen atom or an substituted or unsubstituted alkyl group, l represents an integer of 1 to 3, and p and q each represents an integer of 0 to 2; and a catalyst.

  本发明公开了一种制备交叉偶联化合物的方法，该化合物的化学式为（3）：（Y-）（n-1）R1-R2-（R1）（n' -1）（3），其中R1代表取代或未取代的线性、支链或环烃基，n和n'各自代表1或2，但当n和n'相同时，n和n'均不为2；R2代表取代或未取代的芳基、取代或未取代的杂环基或取代或未取代的烯基，Y代表R2或X1，其中R2如上所定义，X1代表氯、溴或碘原子。该方法包括将化学式为（1）的有机卤化物与化学式为（2）的硼化合物在碱和催化剂的存在下反应，其中化学式（1）中R1如上所定义，X1、n和n'如上所定义，α和β位置相对于X1的碳原子为sp3碳原子，化学式（2）中R2和n'如上所定义，X2独立代表羟基或烷氧基或芳氧基，或X22共同形成烷氧基或芳氧基，m代表1或2，m≤n，硼原子与R2基的sp2碳原子或其硼酸三聚体酐键合。催化剂包括一种镍化合物和一种化学式为（i）的化合物：1其中R3代表取代或未取代的烷基，R4代表氢原子或取代或未取代的烷基，l代表1至3的整数，p和q分别代表0至2的整数。
• METHOD FOR PRODUCING COUPLING COMPOUND
  申请人：Itahashi Tamon

  公开号：US20060281925A1

  公开（公告）日：2006-12-14

  A method is provided for producing a specific crosscoupling compound and a specific catalyst for producing the compound. The method includes reacting in the presence of a base and a nickel compound catalyst organic halide of the formula n′(R 1 X 1 n ), wherein R 1 is a hydrocarbon group and the α and β carbons to X′ are sp 3 carbon atoms; X 1 is a chlorine, bromine, or iodine atoms, and n and n 1 are 1 or 2 but not both 2, with a compound having the formula mR 2 (BX 2 2 ) n′ } where an R 2 is an aryl, heteroaryl, or alkenyl group, and n′ is 1 or 2, X 2 is independently a hydroxyl group, an alkoxy or arylalkoxy group or X 2 2 together form an alkylenedioxy or arylenedioxy group, and m represents 1 or 2 but m≦n, and the boron atom is bonded to a sp 2 carbon atom of R 2 group or a boronic acid trimer anhydride.

  提供了一种生产特定交叉偶联化合物和特定催化剂以生产该化合物的方法。该方法包括在碱和镍化合物催化剂的存在下，将具有以下公式的有机卤化物n’（R1X1n）与具有以下公式的化合物m R2（BX22）n’}反应，其中R1是一个碳氢基团，α和β碳至X’是sp3碳原子；X1是氯、溴或碘原子，n和n1为1或2但不同时为2；R2是芳基、杂环芳基或烯基基团，n’为1或2，X2独立地是羟基、烷氧基或芳基烷氧基，或X22共同形成烷二酮基或芳二酮基；m表示1或2，但m≦n，硼原子与R2基团的sp2碳原子或硼酸三聚体酐键合。
• Production method of a coupling compound
  申请人：Sumitomo Chemical Company, Limited

  公开号：US20040167364A1

  公开（公告）日：2004-08-26

  There is provided a method for producing a coupling compound of formula (1): (Y—) (n−1) R 1 —R 2 —(R 1 ) (n′−1) (1) wherein R 1 , R 2 n and n′ are as defined below, Y is R 2 or X as defined below, which method comprises reacting an organic halogen compound of formula (2): n′(R 1 X 1 n )   (2) wherein X 1 represents a bromine or iodine, R 1 represents a substituted or unsubstituted, linear, branched or cyclic hydrocarbon group of which &agr; and &bgr; carbon atoms in relation to X 1 are sp3 carbon atoms, n and n′ each independently represent an integer of 1 or 2, and provided that n and n′ do not simultaneously represent 2, with an organic boron compound of formula (3): m{R 2 (BX 2 2 ) n′ }  (3) wherein R 2 represents a substituted or unsubstituted aryl group or a substituted or unsubstituted alkenyl group and the boron atom is bonded with a sp2 carbon atom thereof, X 2 represents a hydroxyl or alkoxy group, n′ is as defined above, m represents an integer of 1 or 2, and m is not more than n, in the presence of a catalyst comprising a) a nickel compound, and b) b-1) a compound of formula (i): 1 or b-2) a compound of formula (ii): 2

  提供了一种生产式(1)偶联化合物的方法： (Y-) (n-1) R 1 -R 2 -(R 1 ) (n′-1) (1) 其中 R 1 , R 2 n 和 n′定义如下，Y 是 R 2 或如下定义的X，该方法包括使式(2)的有机卤素化合物反应： n′(R 1 X 1 n ) (2) 其中 X 1 代表溴或碘，R 1 代表取代或未取代的、线性、支链或环状烃基，其中 &agr; 和 &bgr; 碳原子相对于 X 1 均为 sp3 碳原子，n 和 n′各自独立地代表 1 或 2 的整数，且 n 和 n′不同时代表 2，具有式 (3) 的有机硼化合物： m{R 2 (BX 2 2 ) n′ } (3) 其中 R 2 代表取代或未取代的芳基或取代或未取代的烯基，且硼原子与其中的 sp2 碳原子键合，X 2 代表羟基或烷氧基，n′如上定义，m 代表 1 或 2 的整数，且 m 不大于 n。 b) b-1) 式 (i) 的化合物： 1 或 b-2) 式 (ii) 的化合物： 2