N-cinnamyl-2-methylaniline

• 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-cinnamyl-2-methylaniline
• 英文别名: (3-phenyl-allyl)-o-tolyl-amine；Cinnamyl-o-toluidin；2-methyl-N-(3-phenyl-allyl)-aniline；2-methyl-N-(3-phenylprop-2-enyl)aniline
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: GBRCRQWGTNNSJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-cinnamyl-2-methylaniline 在 氧气 、 tris(p-bromophenylammoniumyl) hexachloroantimonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以38%的产率得到2-苯基-8-甲基喹啉
  参考文献：
  名称：

  从N-肉桂基苯胺到sp3 C的2-芳基喹啉的意外构造？催化自由基阳离子盐诱导的H有氧氧化

  摘要：

  cinnamylanilines的一个意想不到的反应物通过的自由基阳离子盐诱导有氧氧化实现SP 3 Ç  H键，从而提供了一系列的2- arylquinolines。机理研究表明，肉桂基苯胺被氧化成亚胺，亚胺被相应的亚胺分解生成的苯胺攻击。进一步分子内环化和芳构化后，获得了2-芳基喹啉。该反应提供了一种从容易获得的起始原料中构建2-芳基喹啉的新方法。

  DOI：

  10.1002/adsc.201500574
• 作为产物：
  描述：

  1-苯基-1-丙炔 、 邻甲苯胺 在 palladium diacetate 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以94%的产率得到N-cinnamyl-2-methylaniline
  参考文献：
  名称：

  使用聚合物负载的三苯基膦-钯配合物作为多相和可回收催化剂，用芳香族和脂肪族胺对内炔进行烯丙基胺化

  摘要：

  开发了一种使用聚合物负载的三苯基膦-钯配合物 [PS-TPP-Pd] 作为高活性非均相可重复使用催化剂对内部炔烃与胺进行烯丙基胺化的简便而新颖的方案。该催化剂表现出显着的活性，可重复使用五个连续循环。该方案适用于各种受阻和官能化的芳香族/脂肪族胺，并以良好到极好的收率提供所需的烯丙基产物。

  DOI：

  10.1002/ejoc.201000463

文献信息

• pH-Mediated Selective Synthesis of N-Allylic Alkylation or N-Alkylation Amines with Allylic Alcohols via an Iridium Catalyst in Water
  作者：Nianhua Luo、Yuhong Zhong、Hongling Shui、Renshi Luo

  DOI：10.1021/acs.joc.1c01930

  日期：2021.11.5

  Amination of allylic alcohols is an effective approach in the facile synthesis of N-allylic alkylation or N-alkylation amines. Recently, a series of catalysts were devised to push forward this transformation. However, current synthetic methods are typically limited to achieve either N-allylic alkylation or N-alkylation products via a certain catalyst. In this article, a pH-mediated selective synthesis of N-allylic

  烯丙醇的胺化是一种简便合成N-烯丙基烷基化或N-烷基化胺的有效方法。最近，设计了一系列催化剂来推动这一转变。然而，目前的合成方法通常仅限于通过某种催化剂获得N-烯丙基烷基化或N-烷基化产物。在本文中，揭示了通过铱催化剂以水作为环境友好溶剂，选择性合成N-烯丙基烷基化或N-烷基化胺与烯丙基醇，从而实现N-烯丙基烷基化和N-烷基化产物的高产率。此外，具有低催化剂负载的克级实验提供了获得用于合成抗真菌药物萘替芬的独特入口的潜力。
• Palladium-catalyzed oxidative arylacetoxylation of alkenes: synthesis of indole and indoline derivatives
  作者：Shuklachary Karnakanti、Zhong-Lin Zang、Sheng Zhao、Pan-Lin Shao、Ping Hu、Yun He

  DOI：10.1039/c7cc06448a

  日期：——

  A method for oxidative arylacetoxylation of alkenes has been developed to synthesize indole and indoline derivatives from readily accessible substrates. The cinnamyl tethered anilines with picolinamide as a directing group provided 3-substituted indoles via intramolecular oxidative arylacetoxylation, and the 2-methyl substituted cinnamyl anilines furnished indoline derivatives with 3-position quaternary

  已经开发了一种用于烯烃的氧化芳基乙酰氧基化的方法，以从容易获得的底物中合成吲哚和二氢吲哚衍生物。以甲基吡啶酰胺为导向基团的肉桂基系苯胺通过分子内氧化芳基乙酰氧基化作用可提供3-取代的吲哚，而2-甲基取代的肉桂基苯胺可通过依次进行分子内氧化芳基乙酰氧基化，水解和水解，使吲哚啉衍生物具有3-位季铵立体中心。氧化步骤。
• Electrochemical trifluoroalkylation/annulation for the synthesis of CF₃-functionalized tetrahydroquinolines and dihydroquinolinones
  作者：Hao-Zeng Wu、Zhong-Shan Teng、Yu-Xin Ke、Yu Zou、Ping Gao、Yue Li、Cheng-He Zhou、Zhong-Lin Zang

  DOI：10.1039/d3ob00987d

  日期：——

  This paper demonstrates tandem trifluoromethylation/C(sp²)–H annulation using Langlois’ reagent as the CF₃ source for the electrochemical synthesis of functionalized tetrahydroquinolines and dihydroquinolinones.

  本文利用 Langlois 试剂作为 CF3 源，展示了串联三氟甲基化/C(sp2)-H 环化反应，用于电化学合成功能化四氢喹啉和二氢喹啉酮。
• Allylation of 1-phenyl-1-propyne with N- and O-pronucleophiles using polymer supported triphenylphosphine palladium complex as a heterogeneous and recyclable catalyst
  作者：Yogesh S. Wagh、Dinesh N. Sawant、Kishor P. Dhake、Krishna M. Deshmukh、Bhalchandra M. Bhanage

  DOI：10.1016/j.tetlet.2011.08.099

  日期：2011.10

  Simple methodology for the allylation of various N- and O-pronucleophiles with 1-phenyl-1-propyne as an allylating agent, using PS-TPP-Pd (polymer supported triphenylphosphine palladium) as a highly active heterogeneous recyclable catalyst has been developed. The protocol is applicable for a wide variety of hindered and functionalized aromatic amines, alcohols, and carboxylic acids. The catalyst exhibited remarkable catalytic activity for five consecutive recycles. (C) 2011 Elsevier Ltd. All rights reserved.
• Pd(OAc)2/dppf as an efficient and highly active catalyst for the allylation of amines, alcohols and carboxylic acids with 1-phenyl-1-propyne
  作者：Yogesh S. Wagh、Dinesh N. Sawant、Pawan J. Tambade、Kishor P. Dhake、Bhalchandra M. Bhanage

  DOI：10.1016/j.tet.2011.02.008

  日期：2011.4

  Pd(OAc)(2)/1,1'-bis(diphenylphosphino)ferrocene as an efficient, highly active catalyst for the allylation of amines, alcohols and carboxylic acids with 1-phenyl-1-propyne has been developed. The effect of various reaction parameters, such as ligand, time, solvent, temperature, metal: ligand ratio and catalyst concentration on yields of the product were investigated. The optimized procedure works well under mild operating conditions and permits rapid generation of a library for various allylated products. (C) 2011 Elsevier Ltd. All rights reserved.