N-(1-phenylethyl) pyridin-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(1-phenylethyl) pyridin-2-amine
• 英文别名: N-(1-phenylethyl)pyridin-2-amine
• 化学式: C₁₃H₁₄N₂
• mdl: MFCD11122791
• 分子量: 198.268
• InChiKey: IWMMJPDCLGWNLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1-phenylethyl) pyridin-2-amine 在 sodium hydride 、 lithium hexamethyldisilazane 作用下， 反应 3.0h， 生成 N-(2-pyridyl)-N-(1-phenylethyl)-2-methylhexanamide
  参考文献：
  名称：

  Parker, Julie A.; Stanforth, Stephen P., Journal of Chemical Research, Miniprint, 1998, # 7, p. 1453 - 1460

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基吡啶 在 二叔丁基过氧化物 、 [Cl2NN]Cu-OtBu 作用下， 以 正戊烷 为溶剂， 反应 24.08h， 生成 N-(1-phenylethyl) pyridin-2-amine
  参考文献：
  名称：

  Copper(II) Anilides in sp³ C-H Amination

  摘要：

  We report a series of novel beta-diketiminato copper(II) anilides [Cl2NN]Cu-NHAr that participate in C-H amination. Reaction of H2NAr (Ar = 2,4,6-Cl3C6H2 (Ar-Cl3), 3,5-(CF3)(2)C6H3 (Ar-F6), or 2-py) with the copper(II) t-butoxide complex [Cl2NN]-Cu-(OBu)-O-t yields the corresponding copper(II) anilides [Cl2NN]-Cu-NHAr. X-ray diffraction of these species reveal three different bonding modes for the anilido moiety: kappa(1)-N in the trigonal [Cl2NN]Cu-NHArCl3 to dinuclear bridging in {[Cl2NN]Cu}(2)(mu-NHArF6)(2) and kappa(2)-N,N in the square planar [Cl2NN]Cu(kappa(2)-NH-2-py). Magnetic data reveal a weak antiferromagnetic interaction through a pi-stacking arrangement of [Cl2NN]Cu-NHArCl3; solution EPR data are consistent with monomeric species. Reaction of [Cl2NN]Cu-NHAr with hydrocarbons R-H (R-H = ethylbenzene and cyclohexane) reveals inefficient stoichiometric C-H amination with these copper(II) anilides. More rapid C-H amination takes place, however, when (BuOOBu)-Bu-t-Bu-t is used, which allows for HAA of R-H to occur from the (BuO center dot)-Bu-t radical generated by reaction of [Cl2NN]Cu and (BuOOBu)-Bu-t-Bu-t. The principal role of these copper(II) anilides [Cl2NN]Cu-NHAr is to capture the radical R-center dot generated from HAA by (BuO center dot)-Bu-t to give functionalized aniline R-NHAr, resulting in a novel amino variant of the Kharasch-Sosnovsky reaction.

  DOI：

  10.1021/ja5026547

文献信息

• Copper-catalyzed direct amination of benzylic hydrocarbons and inactive aliphatic alkanes with arylamines
  作者：Hua Yao、Bo Xie、Xiaoyang Zhong、Shengzhou Jin、Sen Lin、Zhaohua Yan

  DOI：10.1039/d0ob00491j

  日期：——

  A new synthetic method toward direct C-N bond formation through saturated C-H amination of benzylic hydrocarbons and inactive aliphatic alkanes with primary aromatic amines under an inexpensive catalyst/oxidant (Cu/DTBP) system has been developed. Both aminopyridines and anilines could react smoothly with primary and secondary benzylic C-H substrates or cyclohexane to form the corresponding aromatic

  在廉价的催化剂/氧化剂（Cu / DTBP）系统下，已经开发出一种新的合成方法，该方法可通过苄基烃和惰性脂肪族烷烃与伯芳族胺的饱和CH胺化直接形成CN键。氨基吡啶和苯胺均可与伯和仲苄基CH底物或环己烷顺利反应，以中等至良好的收率形成相应的芳族仲胺。该协议的优点是宽泛的官能团耐受性和使用现成的原料。
• A Metal-Free Tandem Demethylenation/C(sp²)–H Cycloamination Process of <i>N</i>-Benzyl-2-aminopyridines via C–C and C–N Bond Cleavage
  作者：Dongdong Liang、Yimiao He、Lanying Liu、Qiang Zhu

  DOI：10.1021/ol4015656

  日期：2013.7.5

  A mild, metal-free synthesis of pyrido[1,2-a]benzimidazoles starting with N-benzyl-2-aminopyridines, which employs PhI(OPiv)2 as a stoichiometric oxidant, has been developed. The process is initiated by an unusual PhI(OPiv)2-mediated ipso SEAr reaction, followed by solvent-assisted C–C and C–N bond cleavage.

  已经开发了一种轻度，无金属的合成方法，该方法以N-苄基-2-氨基吡啶为原料，以PhI（OPiv）2为化学计量氧化剂，合成了吡啶并[1,2- a ]苯并咪唑类化合物。该过程由一个不寻常的岛（OPiv）发起2介导的本位小号ë的Ar反应，接着进行溶剂辅助C-C和C-N键断裂。
• ZnBr ₂ Mediated C−N Bond Formation using Cinnamyl Alcohol and 2‐Amino Pyridines
  作者：Ahwan Panigrahi、Mahadev Sharanappa Sherikar、Kandikere Ramaiah Prabhu

  DOI：10.1002/ejoc.202100463

  日期：2021.6.7

  A new approach has been developed for C−N bond formation using a stoichiometric amount of ZnBr2 from cinnamyl alcohols and 2-amino pyridines. The reaction is also compatible with primary, secondary l, and homoallyl alcohols.

  已经开发了一种使用来自肉桂醇和 2-氨基吡啶的化学计量量的 ZnBr 2形成 CN 键的新方法。该反应还与伯醇、仲醇和高烯丙醇相容。
• N-Alkylation of poor nucleophilic amines and derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate: scope and mechanistic considerations
  作者：Ana Martínez-Asencio、Diego J. Ramón、Miguel Yus

  DOI：10.1016/j.tet.2011.02.075

  日期：2011.4

  simple catalyst for the selective N-monoalkylation of amino derivatives with poor nucleophilic character, such as aromatic and heteroaromatic amines as well as carboxamides, phosphinamides, sulfonamides, and phosphazenes, using in all cases primary alcohols as initial source of the electrophiles, through a hydrogen autotransfer process. In the case of sulfonamides, the monoalkylation process followed

  乙酸铜（II）是一种通用，廉价且简单的催化剂，用于对亲核性较差的氨基衍生物（例如芳族和杂芳族胺以及羧酰胺，次膦酰胺，磺酰胺和磷腈）进行选择性N-单烷基化，在所有情况下均使用伯通过氢自动转移过程，将醇作为亲电试剂的初始来源。在磺酰胺的情况下，单烷基化过程随后是萘催化的还原性脱保护得到伯胺，这是氨直接单烷基化的间接替代方法。使用氘标记试剂对反应进行了研究，表明脱氢和氢化步骤不在同一铜原子配位球上进行，
• Solvent- and catalyst-free direct reductive amination of aldehydes and ketones with Hantzsch ester: synthesis of secondary and tertiary amines
  作者：Quynh Pham Bao Nguyen、Taek Hyeon Kim

  DOI：10.1016/j.tet.2013.04.046

  日期：2013.6

  A facile and rapid method for the parallel synthesis of a series of secondary and tertiary amines by the direct reductive amination of aldehydes and ketones with Hantzsch ester under solvent- and catalyst-free has been developed. The scope and limitation of this method are described.

  已经开发了一种简便，快速的方法，该方法通过在无溶剂和无催化剂的情况下，用Hantzsch酯对醛和酮进行直接还原胺化反应，来并行合成一系列仲胺和叔胺。描述了该方法的范围和局限性。