2-C6H4FCHNCH2CH2NMe2 | 126610-82-0

• 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: 2-C6H4FCHNCH2CH2NMe2
• 英文别名: 2-{(E)-[(2-Fluorophenyl)methylidene]amino}-N,N-dimethylethan-1-amine；2-[(2-fluorophenyl)methylideneamino]-N,N-dimethylethanamine
• CAS: 126610-82-0
• 化学式: C₁₁H₁₅FN₂
• 分子量: 194.252
• InChiKey: KCSNIUVSADMJGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-C6H4FCHNCH2CH2NMe2 以 not given 为溶剂， 生成
  参考文献：
  名称：

  芳基-卤素键与铂（II）的氧化加成以及由芳基-氟化物氧化加成形成的配合物的结构

  摘要：

  当Ar = 2-BrC 6 H 4，2 -CIC 6 H 4或C 6 F 5时，配合物[PtMe 2（Me 2 NCH 2 CH 2 N CHAr）]通过芳基-卤素键的氧化加成反应，但通过Ar = 2-FC 6 H 4或C 6 H 5时，以及Ar = C 6 F 5时，进行邻位金属化，氧化加成产物通过亚胺键加成丙酮，形成的络合物在晶体学上被表征为氢键二聚体。与氧化加成反应的反应性可能与C–X键能相关。

  DOI：

  10.1039/c39890001297

文献信息

• Intramolecular oxidative addition of C–F and C–H bonds to [Pt(dba)2]. Crystal structure of [PtCl{Me2NCH2CH2NCH(2,4,5-C6HF3)}]
  作者：Margarita Crespo、Jaume Granell、Mercè Font-Bardı́a、Xavier Solans

  DOI：10.1016/j.jorganchem.2004.06.060

  日期：2004.9

  produced cyclometallated platinum (II) compounds [PtX(Me2NCH2CH2NCHR)] (X = Br, Cl) (2) containing a terdentate [C,N,N′] ligand. The obtained compounds were fully characterized including a structure determination for [PtClMe2NCH2CH2NCH(2,4,5-C6HF3)}] (2d′).

  当化合物[Pt（dba）2 ]与配体RCHNCH 2 CH 2 NMe 2（1a – 1f）（其中R是氟化芳基环）的反应时，当两个氟原子存在于邻位时，会激活C–F键。邻位仅含一个氟取代基的配体的芳基环或C–H键的活化。环的氟化程度的增加有利于CF和CH键的活化。与卤化锂进一步反应，生成环金属化的铂（II）化合物[PtX（Me 2 NCH 2 CH 2 NCHR）]（X = Br，Cl）（2）含有一个[C，N，N ']的配体。所获得的化合物被充分表征，包括[PtCl Me 2 NCH 2 CH 2 NCH（2,4,5-C 6 HF 3）}]的结构测定（2d '）。
• Activation of aromatic carbon-fluorine bonds by organoplatinum complexes
  作者：Craig M. Anderson、Margarita Crespo、George Ferguson、Alan J. Lough、Richard J. Puddephatt

  DOI：10.1021/om00039a025

  日期：1992.3

  The ligand Me2NCH2CH2N = CHC6F5 (1a) reacts with [Pt2Me4(mu-SMe2)2] (2) in acetone solution to give sequentially [PtMe2(Me2NCH2CH2N = CHC6F5)] (3a), [PtFMe2(Me2NCH2CH2N = CHC6F5)] (4), and [PtFMe2Me2NCH2CH2NHCH(CH2COMe)C6F4}] (5). Complex 5, which is formed by reaction of 4 with acetone, was characterized by an X-ray structure determination and shown to contain hydrogen-bonded NH...FPt dimers in the solid state. The ligand PhN = CHC6F5 (6) reacts with 2 to give [PtFMe2(PhN = CHC6F4)(SMe2)] which may exist in two isomeric forms 7a and 7b. The reactions to form 4 and 7 give the first examples of oxidative addition of C-F bonds to platinum(II). The ligand Me2NCH2CH2N = CH (2,6-C6H3F2) reacts with 2 to give [PtMe2Me2NCH2CH2N = CH(2,6-C6H3F2)}] (3b), but this failed to give oxidative addition of a C-F bond. The ligands Me2NCH2CH2N = CHAr, Ar = 2,6-, 2,5-, or 2,3-C6H3F2, react with 2 to give [PtMe2(Me2NCH2CH2N = CHAr)], and then CH4 and [PtMe(Me2NCH2CH2N = CHC6H2F2)]. These reactions involve activation of a C-H bond rather than a C-F bond of the aryl group. The results show that activation of a C-F bond of a pentafluorophenyl group is facilitated by incorporation into a monodentate or bidentate nitrogen-donor ligand so that intramolecular oxidative addition can occur, but that C-H bond activation is always easier than C-F bond activation in C6H(x)F5-x groups and that more than two fluorine substituents on the phenyl group are necessary for C-F bond activation to occur.
• Competition between intramolecular oxidative addition and ortho metalation in organoplatinum(II) compounds: activation of aryl-halogen bonds
  作者：Craig M. Anderson、Margarita Crespo、Michael C. Jennings、Alan J. Lough、George Ferguson、Richard J. Puddephatt

  DOI：10.1021/om00054a031

  日期：1991.8

  The ligands 2-XC6H4CH = NCH2CH2NMe2 (1) react with [Pt2Me4(mu-SMe2)2] (2) to give [PtMe2(2-XC6H4CH = NCH2CH2NMe2)] (3), which then react either by ortho metalation to give CH4 and [PtMe-(2-XC6H3CH = NCH2CH2NMe2)] (4) or undergo oxidative addition of the C-X bond to give [PtXMe2-(C6H4CH = NCH2CH2NMe2)] (5). These complexes, and related compounds with modified aryl substituents, have been characterized by NMR spectroscopy, and the derivative [PtClMe2(ClC6H3CH = NCH2CH2NMe2)] (7b) has been characterized crystallographically. The complex [PtMe(C6H4CH = NCH2CH2NMe2)] reacts with CD3Br or MeI to give [PtBrMe(CD3)(C6H4CH = NCH2CH2NMe2)] or [PtIMe2(C6H4CH = NCH2CH2NMe2)], respectively, initially by trans oxidative addition. The ligands 2-XC6H4CH = NR (R = Ph, Pr) react with [Pt2Me4(mu-SMe2)2] to give similar products of ortho metalation, [PtMe(2-XC6H3CH = NR)(SMe2)], or oxidative addition, [PtXMe2(C6H4CH = NR)(SMe2)]. The kinetics of the reaction of 3 to give 4 or 5 have been studied, and the reactions each follow first-order kinetics. The activation parameters for both types of reaction are similar, and since the ortho metalation is presumed to occur by concerted C-H oxidative addition followed by rapid reductive elimination of methane, it is suggested that the oxidative addition of aryl-bromide or aryl-chloride bonds also occurs by a concerted mechanism. The rates of reaction are C-Br > C-Cl > C-H, and internal competition reactions give the sequence C-Cl > C-H > C-F. Hence, the overall reactivity series is C-Br > C-Cl > C-H > C-F, the series of increasing C-X bond energies. These are the first examples of aryl-halogen bond activation by platinum(II) complexes.
• Oxidative addition of aryl–halogen bonds to platinum(<scp>II</scp>) and the structure of a complex formed by aryl–fluoride oxidative addition
  作者：Craig M. Anderson、Richard J. Puddephatt、George Ferguson、Alan J. Lough

  DOI：10.1039/c39890001297

  日期：——

  The complexes [PtMe2(Me2NCH2CH2NCHAr)] react by oxidative addition of the aryl–halogen bond when Ar = 2-BrC6H4, 2-CIC6H4, or C6F5 but by ortho-metallation when Ar = 2-FC6H4 or C6H5, and in the case where Ar = C6F5, the oxidative addition product adds acetone across the imine bond and the complex formed has been characterized crystallographically as a hydrogen-bonded dimer; the reactivity to oxidative

  当Ar = 2-BrC 6 H 4，2 -CIC 6 H 4或C 6 F 5时，配合物[PtMe 2（Me 2 NCH 2 CH 2 N CHAr）]通过芳基-卤素键的氧化加成反应，但通过Ar = 2-FC 6 H 4或C 6 H 5时，以及Ar = C 6 F 5时，进行邻位金属化，氧化加成产物通过亚胺键加成丙酮，形成的络合物在晶体学上被表征为氢键二聚体。与氧化加成反应的反应性可能与C–X键能相关。