6-allyl-3-chloro-2-methyl-N-(2-methylallyl)aniline | 1255773-57-9

• 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: 6-allyl-3-chloro-2-methyl-N-(2-methylallyl)aniline
• 英文别名: 3-chloro-2-methyl-N-(2-methylprop-2-enyl)-6-prop-2-enylaniline
• CAS: 1255773-57-9
• 化学式: C₁₄H₁₈ClN
• 分子量: 235.757
• InChiKey: BIMQEAUOHQOQBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  6-allyl-3-chloro-2-methyl-N-(2-methylallyl)aniline 在 sodium tungstate (VI) dihydrate 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 生成 C₁₄H₁₆ClNO
  参考文献：
  名称：

  Rational use of substituted N-allyl and N,N-diallylanilines in the stereoselective synthesis of novel 2-alkenyltetrahydro-1-benzazepines

  摘要：

  Two new series of 1,4-epoxy-2-exo-vinyl(isopropenyl)tetrahydro-1-benzazepines and cis-2-vinyl(isopropenyl)-4-hydroxytetrahydro-1-benzazepines were prepared by an efficient three/four-step route from available substituted N,N-diallylanilines and mono N-allylanilines. The amino-Claisen rearrangement and the sequential oxidation/intramolecular 1,3-dipolar cycloaddition reactions were used as the key steps in this synthesis. All the synthesized compounds were fully characterized by IR. GC MS and NMR techniques. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.067
• 作为产物：
  描述：

  6-allyl-3-chloro-2-methylaniline 、 3-氯-2-甲基丙烯 在 sodium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以69%的产率得到6-allyl-3-chloro-2-methyl-N-(2-methylallyl)aniline
  参考文献：
  名称：

  Rational use of substituted N-allyl and N,N-diallylanilines in the stereoselective synthesis of novel 2-alkenyltetrahydro-1-benzazepines

  摘要：

  Two new series of 1,4-epoxy-2-exo-vinyl(isopropenyl)tetrahydro-1-benzazepines and cis-2-vinyl(isopropenyl)-4-hydroxytetrahydro-1-benzazepines were prepared by an efficient three/four-step route from available substituted N,N-diallylanilines and mono N-allylanilines. The amino-Claisen rearrangement and the sequential oxidation/intramolecular 1,3-dipolar cycloaddition reactions were used as the key steps in this synthesis. All the synthesized compounds were fully characterized by IR. GC MS and NMR techniques. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.067

文献信息

• Hydrogen-bonded dimers, chains and rings in six differently substituted 2-vinyltetrahydro-1,4-epoxy-1-benzazepines
  作者：Lina M. Acosta、Alirio Palma、Ali Bahsas、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270110009017

  日期：2010.4.15

  In (2SR, 4RS)-2-exo-vinyl-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(12)H(13)NO, (I), the molecules are linked by two independent C-H center dot center dot center dot pi (arene) hydrogen bonds to form sheets, such that all of the molecules in a given sheet are of the same configuration. The molecules of (2SR, 4RS)-7-chloro-2exo-(2-methylprop-1-enyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy1- benzazepine, C(14)H(16)ClNO, (II), are linked by a C-H center dot center dot center dot O hydrogen bond into C(4) chains, where all the molecules in a given chain are of the same configuration, whereas the molecules of (2SR, 4RS)-8-chloro-9-methyl-2-exo-(2-methylprop1- enyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C(15)H(18)ClNO, (III), are linked into centrosymmetric dimers by pairs of symmetry-related C-H center dot center dot center dot pi (arene) hydrogen bonds. (2RS, 4RS)-8-Chloro-9-methyl-2-endo-(2-methylprop-1-enyl)2,3,4,5- tetrahydro-1H-1,4-epoxy-1-benzazepine, C(15)H(18)ClNO, (IV), is a diastereoisomer of (III) and, as for (II), a single C-H center dot center dot center dot O hydrogen bond links the molecules into C(4) chains, each containing molecules of a single configuration. The structure of (2SR, 4RS)-8-chloro-9-methyl-2-exo-(prop-1-en-2-yl)2,3,4,5- tetrahydro-1H-1,4-epoxy-1-benzazepine, C(14)H(16)ClNO, (V), contains a C-H center dot center dot center dot O hydrogen bond which links pairs of molecules into centrosymmetric R2 2(6) dimers. (2SR, 4RS)-7,9Dichloro- 2-exo-(prop-1-en-2-yl)-2,3,4,5-tetrahydro-1H-1,4epoxy- 1-benzazepine, C(13)H(13)Cl(2)NO, (VI), is an inversion twin containing both the (2S, 4R) and (2R, 4S) enantiomers in the space group P2(1), and a C-H center dot center dot center dot O hydrogen bond links molecules of a given configuration into simple C(3) chains.
• Rational use of substituted N-allyl and N,N-diallylanilines in the stereoselective synthesis of novel 2-alkenyltetrahydro-1-benzazepines
  作者：Lina María Acosta、Alirio Palma、Alí Bahsas

  DOI：10.1016/j.tet.2010.08.067

  日期：2010.10

  Two new series of 1,4-epoxy-2-exo-vinyl(isopropenyl)tetrahydro-1-benzazepines and cis-2-vinyl(isopropenyl)-4-hydroxytetrahydro-1-benzazepines were prepared by an efficient three/four-step route from available substituted N,N-diallylanilines and mono N-allylanilines. The amino-Claisen rearrangement and the sequential oxidation/intramolecular 1,3-dipolar cycloaddition reactions were used as the key steps in this synthesis. All the synthesized compounds were fully characterized by IR. GC MS and NMR techniques. (C) 2010 Elsevier Ltd. All rights reserved.