(2-Allyl-naphthalen-1-yl)-benzyl-amine | 909296-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-Allyl-naphthalen-1-yl)-benzyl-amine
• 英文别名: N-benzyl-2-prop-2-enylnaphthalen-1-amine
• CAS: 909296-99-7
• 化学式: C₂₀H₁₉N
• 分子量: 273.378
• InChiKey: WNHAKRPPAJOOIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  (2-Allyl-naphthalen-1-yl)-benzyl-amine 在 sodium tungstate (VI) dihydrate 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and in vitro activity of new tetrahydronaphtho[1,2-b]azepine derivatives against Trypanosoma cruzi and Leishmania chagasi parasites

  摘要：

  Series of 2-exo-aryl-1,4-epoxy-2,3,4,5-tetrahydronaphtho[1,2-b]azepines 3a-k and cis-2-aryl-4-hydroxy2,3,4,5-tetrahydronaphtho[1,2-b] azepines 4a-j were synthesized and evaluated against free and intracellular live forms of Trypanosoma cruzi and Leishmania chagasi parasites using in vitro assays. Cell toxicity was also analyzed on Vero and THP-1 mammalian cell lines. The compounds 3c, 3f, and 4d were the most active against both live forms of T. cruzi parasites with low mammalian cell toxicity. Some compounds were active on free live forms of L. chagasi parasites but none was active on intracellular amastigotes of L. chagasi infecting THP-1 macrophages. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.013
• 作为产物：
  描述：

  N-苄基-1-萘胺 在 三氟化硼乙醚 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 (2-Allyl-naphthalen-1-yl)-benzyl-amine
  参考文献：
  名称：

  2-烯丙基-N-苄基取代的α-萘胺作为杂环合成的基础。苯并[ e ]萘并[1,2- b ]氮杂和萘并[1,2- b ]氮杂的新型高效合成方法

  摘要：

  一系列新的13-乙酰基-7,12-二氢-7-乙基苯并[ e ]萘[1,2- b ]氮杂（4a – d）和2-芳基-4-羟基-2,3,4,5 N-烯丙基-N-苄基取代的α-萘胺（1a - d）是利用芳香族氨基-克莱森重排，分子内Friedel-Crafts烷基化和N-烯丙基-N-苄基取代的α-萘胺合成的-四氢萘并[1,2- b ] a庚因衍生物（6a - d）。分子内偶极1，3-环加成的硝烯-烯烃反应。

  DOI：

  10.1016/j.tetlet.2006.04.160

文献信息

• Design, scope and mechanism of highly active and selective chiral NHC–iridium catalysts for the intramolecular hydroamination of a variety of unactivated aminoalkenes
  作者：Daven Foster、Pengchao Gao、Ziyun Zhang、Gellért Sipos、Alexandre N. Sobolev、Gareth Nealon、Laura Falivene、Luigi Cavallo、Reto Dorta

  DOI：10.1039/d0sc05884j

  日期：——

  Chiral, cationic NHC–iridium complexes are introduced as catalysts for the intramolecular hydroamination reaction of unactivated aminoalkenes. The catalysts show high activity in the construction of a range of 5- and 6-membered N-heterocycles, which are accessed in excellent optical purity, with various functional groups being tolerated with this system. A major deactivation pathway is presented and

  引入手性阳离子 NHC-铱配合物作为未活化氨基烯烃分子内氢胺化反应的催化剂。该催化剂在构建一系列 5 元和 6 元 N 杂环时表现出高活性，这些杂环具有优异的光学纯度，并且该系统可以耐受各种官能团。通过使用替代反应条件呈现和消除主要的失活途径。对反应机理进行了详细的实验和计算研究，为催化系统的作用模式提供了有价值的见解，并指出了对该催化平台的未来修改。
• Crystal Structure of 2-Exo-Phenyl-2,3,4,5-Tetrahydro-1,4-Epoxinafto[1,2-b]azepine
  作者：Vicmar E. Gonzalez、Luis A. Vizcaya、Asiloé J. Mora、Gerzon E. Delgado、Ali Bahsas、Andrés F. Yépes、Alirio Palma

  DOI：10.1007/s10870-011-0253-x

  日期：2012.4

  The title compound, C20H17NO, crystallizes in the orthorhombic P212121 space group with unit cell parameters a = 7.6903(7) Å, b = 18.979(2) Å, c = 19.753(2) Å, with two crystallographically independent molecules in the asymmetric unit, which differ from one another in the slight rotation of the phenyl ring; this allows the formation of three internal hydrogen bonds, two of the type C–H···N and one of the type C–H···O, in one of the molecules, in contrast with only two of the type C–H···N in the other. The compound is rich in aromatic π rings and therefore the crystal packing is entirely dominated by cohesive weak C–H···π interactions among neighboring molecules producing an efficient packing with 71.2% of occupied space. The molecules of the title compound, C20H17NO, are joined by C–H···N and C–H···O hydrogen bonds. The compound is rich in aromatic π rings and therefore the crystal packing is entirely dominated by cohesive weak C–H···π interactions among neighboring molecules producing an efficient packing with 71.2% of occupied space.

  标题化合物 C20H17NO 在正交 P212121 空间群中结晶，其单胞参数为 a = 7.6903(7) 埃，b = 18.979(2) 埃，c = 19.753(2) 埃。753(2) 埃，在不对称单元中有两个晶体学上独立的分子，它们之间的区别在于苯环的轻微旋转；这使得其中一个分子中形成了三个内部氢键，两个为 C-H-N 型，一个为 C-H-O 型，而另一个分子中只有两个 C-H-N 型。该化合物富含芳香π环，因此晶体的堆积完全由相邻分子间内聚的弱 C-H---π 相互作用所主导，从而产生了有效的堆积，占据了 71.2% 的空间。标题化合物 C20H17NO 的分子通过 C-H-N 和 C-H-O 氢键连接。该化合物富含芳香 π 环，因此晶体堆积完全由相邻分子间内聚的弱 C-H---π 相互作用所主导，从而产生了有效堆积，占据了 71.2% 的空间。
• 2-Allyl-N-benzyl substituted α-naphthylamines as building blocks in heterocyclic synthesis. New and efficient syntheses of benz[e]naphtho[1,2-b]azepine and naphtho[1,2-b]azepine derivatives
  作者：Andrés Felipe Yépez、Alirio Palma、Elena Stashenko、Ali Bahsas、Juan M. Amaro-Luis

  DOI：10.1016/j.tetlet.2006.04.160

  日期：2006.8

  A new series of 13-acetyl-7,12-dihydro-7-ethylbenz[e]naphtho[1,2-b]azepine (4a–d) and 2-aryl-4-hydroxy-2,3,4,5-tetrahydronaphtho[1,2-b]azepine derivatives (6a–d) have been synthesized from N-allyl-N-benzyl substituted α-naphthylamines (1a–d) by utilizing aromatic amino-Claisen rearrangement, intramolecular Friedel–Crafts alkylation and intramolecular dipolar 1,3-cycloaddition nitrone-olefin reactions

  一系列新的13-乙酰基-7,12-二氢-7-乙基苯并[ e ]萘[1,2- b ]氮杂（4a – d）和2-芳基-4-羟基-2,3,4,5 N-烯丙基-N-苄基取代的α-萘胺（1a - d）是利用芳香族氨基-克莱森重排，分子内Friedel-Crafts烷基化和N-烯丙基-N-苄基取代的α-萘胺合成的-四氢萘并[1,2- b ] a庚因衍生物（6a - d）。分子内偶极1，3-环加成的硝烯-烯烃反应。
• Synthesis and in vitro activity of new tetrahydronaphtho[1,2-b]azepine derivatives against Trypanosoma cruzi and Leishmania chagasi parasites
  作者：Alirio Palma、Andrés Felipe Yépes、Sandra Milena Leal、Carlos Andrés Coronado、Patricia Escobar

  DOI：10.1016/j.bmcl.2008.05.013

  日期：2009.4

  Series of 2-exo-aryl-1,4-epoxy-2,3,4,5-tetrahydronaphtho[1,2-b]azepines 3a-k and cis-2-aryl-4-hydroxy2,3,4,5-tetrahydronaphtho[1,2-b] azepines 4a-j were synthesized and evaluated against free and intracellular live forms of Trypanosoma cruzi and Leishmania chagasi parasites using in vitro assays. Cell toxicity was also analyzed on Vero and THP-1 mammalian cell lines. The compounds 3c, 3f, and 4d were the most active against both live forms of T. cruzi parasites with low mammalian cell toxicity. Some compounds were active on free live forms of L. chagasi parasites but none was active on intracellular amastigotes of L. chagasi infecting THP-1 macrophages. (C) 2008 Elsevier Ltd. All rights reserved.