N-benzhydryl-4-bromoaniline | 1036577-18-0

• 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: N-benzhydryl-4-bromoaniline
• CAS: 1036577-18-0
• 化学式: C₁₉H₁₆BrN
• 分子量: 338.247
• InChiKey: CZXLHZDAMGSAPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzhydryl-4-bromoaniline 在 potassium hydride 作用下， 以 乙腈 为溶剂， 反应 0.33h， 生成
  参考文献：
  名称：

  Hydride, Hydrogen, Proton, and Electron Affinities of Imines and Their Reaction Intermediates in Acetonitrile and Construction of Thermodynamic Characteristic Graphs (TCGs) of Imines as a “Molecule ID Card”

  摘要：

  A series of 61 imines with various typical structures were synthesized, and the thermodynamic affinities (defined as enthalpy changes or redox potentials in this work) of the imines to abstract hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the imines to abstract hydrogen atoms and protons, and the thermodynamic affinities of the hydrogen adducts of the imines to abstract electrons in acetonitrile were determined by using titration calorimetry and electrochemical methods. The pure heterolytic and homolytic dissociation energies of the C = N pi-bond in the imines were estimated. The polarity of the C = N double bond in the imines was examined using a linear free-energy relationship. The idea of a thermodynamic characteristic graph (TCG) of imines as an efficient "Molecule ID Card" was introduced. The TCG can be used to quantitatively diagnose and predict the characteristic chemical properties of imines and their various reaction intermediates as well as the reduction mechanism of the imines. The information disclosed in this work could not only supply a gap of thermodynamics for the chemistry of imines but also strongly promote the fast development of the applications of imines.

  DOI：

  10.1021/jo902332n
• 作为产物：
  描述：

  4-溴-N-(二苯亚甲基)苯胺 在 (4,4'-di-tert-butyl-2,2'-bipyridine)bis(2-phenylpyridine)iridium(III) hexafluorophosphate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.15h， 以84%的产率得到N-benzhydryl-4-bromoaniline
  参考文献：
  名称：

  快速连续流光氧化还原催化芳基亚胺的化学选择性和可规模化转移氢化

  摘要：

  在竞争性可还原基团存在下，二芳基亚胺的化学选择性还原是通过连续流可见光光氧化还原催化精确控制反应和照射时间来实现的。该方法能够在卤化物、酯、酮和氰基等敏感官能团存在下对二芳基亚胺进行温和有效的转移氢化。该流程方案高效、快速（9 分钟内转化率>98%），并且易于扩展以提供数克数量的高纯度胺产品。

  DOI：

  10.2533/chimia.2019.823

文献信息

• Zinc Chloride Mediated Nucleophilic Substitution: Amination and Thioetherification of Alcohols at Room Temperature
  作者：Ashima Singh、Shruti Gupta、Jitender M. Khurana

  DOI：10.1080/00304948.2020.1716617

  日期：2020.3.3

  Catalytic chemistry is one of the focal points for the development of environmentally benign organic transformations. It is true that the employment of catalysts in organic transformations comes wi...

  催化化学是开发环境友好型有机转化的重点之一。确实，在有机转化中使用催化剂是...
• Iron-Catalyzed CC Bond Cleavage and CN Bond Formation
  作者：Wenjuan Li、Xiaojian Zheng、Zhiping Li

  DOI：10.1002/adsc.201200324

  日期：2013.1.14

  A novel approach for CN bond formation was developed by iron‐catalyzed CC bond cleavage. Anilines and sulfonamides reacted smoothly with 2‐substituted 1,3‐diphenylpropane‐1,3‐diones to afford N‐alkylation products, in which the 1,3‐dicarbonyl group acts as a leaving group in the presence of an iron catalyst. The reversible CC bond cleavage plays a driving force to give the thermodynamically stable

  铁催化的CC键裂解产生了一种形成CN键的新方法。苯胺和磺酰胺与2-取代的1,3-二苯基丙烷-1,3-二酮平稳反应，得到N-烷基化产物，其中1,3-二羰基在铁催化剂存在下充当离去基团。可逆的CC键断裂起着驱动力的作用，从而提供了热力学稳定的产物。该方法是对以前形成CN键的方法的补充。
• Silver-Catalyzed N–H Functionalization of Aryl/Aryl Diazoalkanes with Anilines
  作者：Feifei He、Claire Empel、Rene M. Koenigs

  DOI：10.1021/acs.orglett.1c02289

  日期：2021.9.3

  Herein, we report on the N–H functionalization reaction of primary and secondary anilines with diaryldiazoalkanes using simple AgPF6 as catalyst. We demonstrated broad applicability in the reaction of diaryldiazoalkanes with different anilines (31 examples, up to 97% yield). Furthermore, we propose a possible reaction mechanism for the N–H functionalization.

  在此，我们报告了使用简单的 AgPF 6作为催化剂的伯和仲苯胺与二芳基重氮烷烃的 N-H 官能化反应。我们证明了二芳基重氮烷烃与不同苯胺反应的广泛适用性（31 个例子，产率高达 97%）。此外，我们提出了 N-H 官能化的可能反应机制。
• Hydride, Hydrogen, Proton, and Electron Affinities of Imines and Their Reaction Intermediates in Acetonitrile and Construction of Thermodynamic Characteristic Graphs (TCGs) of Imines as a “Molecule ID Card”
  作者：Xiao-Qing Zhu、Qiao-Yun Liu、Qiang Chen、Lian-Rui Mei

  DOI：10.1021/jo902332n

  日期：2010.2.5

  A series of 61 imines with various typical structures were synthesized, and the thermodynamic affinities (defined as enthalpy changes or redox potentials in this work) of the imines to abstract hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the imines to abstract hydrogen atoms and protons, and the thermodynamic affinities of the hydrogen adducts of the imines to abstract electrons in acetonitrile were determined by using titration calorimetry and electrochemical methods. The pure heterolytic and homolytic dissociation energies of the C = N pi-bond in the imines were estimated. The polarity of the C = N double bond in the imines was examined using a linear free-energy relationship. The idea of a thermodynamic characteristic graph (TCG) of imines as an efficient "Molecule ID Card" was introduced. The TCG can be used to quantitatively diagnose and predict the characteristic chemical properties of imines and their various reaction intermediates as well as the reduction mechanism of the imines. The information disclosed in this work could not only supply a gap of thermodynamics for the chemistry of imines but also strongly promote the fast development of the applications of imines.
• A Chemoselective and Scalable Transfer Hydrogenation of Aryl Imines by Rapid Continuous Flow Photoredox Catalysis
  作者：Rowan L. Pilkington、Nikolai P. Rossouw、Dean J. Van As、Anastasios Polyzos

  DOI：10.2533/chimia.2019.823

  日期：——

  accessed through precise control of reaction and irradiation time by continuous flow visible light photoredox catalysis. The method enables the mild and efficient transfer hydrogenation of diaryl imines in the presence of sensitive functionality including halides, ester, ketone, and cyano groups. The flow protocol is efficient, rapid (>98% conversion within 9 min) and readily scaled to deliver multigram

  在竞争性可还原基团存在下，二芳基亚胺的化学选择性还原是通过连续流可见光光氧化还原催化精确控制反应和照射时间来实现的。该方法能够在卤化物、酯、酮和氰基等敏感官能团存在下对二芳基亚胺进行温和有效的转移氢化。该流程方案高效、快速（9 分钟内转化率>98%），并且易于扩展以提供数克数量的高纯度胺产品。