N-benzyl-2-chloro-4-methylaniline | 900790-27-4

• 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-benzyl-2-chloro-4-methylaniline
• CAS: 900790-27-4
• 化学式: C₁₄H₁₄ClN
• mdl: MFCD11180104
• 分子量: 231.725
• InChiKey: ULNPPRMTXSOALK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 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-benzyl-2-chloro-4-methylaniline 在 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 醋酸异丙酯 、 异丙醇 为溶剂， 反应 25.17h， 生成 1-苄基-5-甲基-1,3-二氢-2H-苯并咪唑-2-酮
  参考文献：
  名称：

  Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization

  摘要：

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.

  DOI：

  10.1021/ol061233j
• 作为产物：
  描述：

  苯甲醛 、 2-氯-4-甲基苯胺 在 硫脲 二氢吡啶 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以73%的产率得到N-benzyl-2-chloro-4-methylaniline
  参考文献：
  名称：

  Thiourea-Catalyzed Direct Reductive Amination of Aldehydes

  摘要：

  报道了一种氢键催化的醛直接还原胺化反应。该过程不使用酸和金属，以硫脲作为有机催化剂，采用Hantzsch酯进行转移氢化，能够高效合成多种胺类。

  DOI：

  10.1055/s-2006-939052

文献信息

• Radical Cation Salt-initiated Aerobic C−H Phosphorylation of <i>N</i> -Benzylanilines: Synthesis of α-Aminophosphonates
  作者：Xiaodong Jia、Xiaofei Liu、Yu Yuan、Pengfei Li、Wentao Hou、Kaixuan He

  DOI：10.1002/asia.201800584

  日期：2018.8.6

  A radical cation salt‐initiated phosphorylation of N‐benzylanilines was realized through an aerobic oxidation of the sp3 C−H bond, providing a series of α‐aminophosphonates in high yields. An investigation of the reaction scope revealed that this mild catalyst system is superior in good functional group tolerance and high reaction efficiency. The mechanistic study implied that the cleavage of the sp3

  N-苄基苯胺的自由基阳离子盐引发的磷酸化通过对sp 3 C-H键的需氧氧化实现，从而以高收率提供了一系列α-氨基膦酸酯。对反应范围的研究表明，该温和的催化剂体系在良好的官能团耐受性和高反应效率方面是优异的。机理研究表明，sp 3 C-H键的断裂参与了速率确定步骤。
• Thiourea-Catalyzed Direct Reductive Amination of Aldehydes
  作者：Dirk Menche、Fatih Arikan

  DOI：10.1055/s-2006-939052

  日期：——

  A hydrogen-bond-catalyzed direct reductive amination of aldehydes is reported. The acid- and metal-free process uses thiourea as organocatalyst and the Hantzsch ester for transfer-hydrogenation and allows for the high-yielding synthesis of diverse amines.

  报道了一种氢键催化的醛直接还原胺化反应。该过程不使用酸和金属，以硫脲作为有机催化剂，采用Hantzsch酯进行转移氢化，能够高效合成多种胺类。
• Efficient Access to Cyclic Ureas via Pd-Catalyzed Cyclization
  作者：Mark McLaughlin、Michael Palucki、Ian W. Davies

  DOI：10.1021/ol061233j

  日期：2006.7.1

  An efficient regioselective method for the preparation of structurally diverse imidazopyridinones and benzoimidazolones starting from readily available and economical starting materials is described. High-yielding reductive alkylation of electron-deficient o-haloarylamines followed by treatment with inexpensive N-chlorosulfonyl isocyanate afforded primary ureas in good overall yields. A Pd-catalyzed urea cyclization reaction furnished imidazopyridinones and benzoimidazolones in excellent yields. Overall, the developed chemistry provides rapid access to pharmaceutically important heterocyclic compounds with high efficiency.