(E)-3-(N-(2-methylprop-1-yl)amino)phenylprop-1-ene | 144608-94-6

• 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: (E)-3-(N-(2-methylprop-1-yl)amino)phenylprop-1-ene
• 英文别名: N-cinnamyl-N-isobutylamine；2-methyl-N-[(E)-3-phenylprop-2-enyl]propan-1-amine
• CAS: 144608-94-6
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: PMBUEBBTUPUBQW-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  (E)-3-(N-(2-methylprop-1-yl)amino)phenylprop-1-ene 在 三甲基铝 、 对甲苯磺酸 作用下， 以 甲苯 、 苯 为溶剂， 反应 5.0h， 生成 [2,2-Dimethyl-3-phenyl-pent-4-en-(E)-ylidene]-isobutyl-amine
  参考文献：
  名称：

  Studies of the regiospecific 3-aza-Cope rearrangement promoted by electrophilic reagents

  摘要：

  The 3-aza-Cope rearrangement of N-alkyl-N-allyl enamine substrates, which required temperatures of 250 250-degrees-C to proceed thermally, was promoted at 111-degrees-C in the presence of electrophilic reagents such as HCl (0.5 equiv) TiCl4 (0.2 equiv), AlMe3 (1.2 equiv), or (ArO)2AlMe (1.2 equiv). In order to probe the regioselectivity of this accelerated carbon-carbon bond forming process under these reaction conditions, several enamine substrates were prepared from both isobutyraldehyde and cyclohexanone. Each substrate used in these studies was prepared having an unsymmetrical N-allylic group, substituted with either an alkyl or phenyl substituent at the 4 or 6 position of the 3-aza-Cope framework. In all cam examined, reaction acceleration by the electrophilic reagent produced regiospecific [3,3] rearrangement to the corresponding products resulting from [1,3] rearrangement were not observed. Hydride reduction of the resulting imines generated the delta,epsilon-unsaturated amines in 55-94% overall yield in the three-step condensation-rearrangement-reduction process from the secondary allylamine.

  DOI：

  10.1021/jo00052a037
• 作为产物：
  描述：

  Isobutyl-[(E)-3-phenyl-prop-2-en-(E)-ylidene]-amine 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 生成 (E)-3-(N-(2-methylprop-1-yl)amino)phenylprop-1-ene
  参考文献：
  名称：

  Studies of the regiospecific 3-aza-Cope rearrangement promoted by electrophilic reagents

  摘要：

  The 3-aza-Cope rearrangement of N-alkyl-N-allyl enamine substrates, which required temperatures of 250 250-degrees-C to proceed thermally, was promoted at 111-degrees-C in the presence of electrophilic reagents such as HCl (0.5 equiv) TiCl4 (0.2 equiv), AlMe3 (1.2 equiv), or (ArO)2AlMe (1.2 equiv). In order to probe the regioselectivity of this accelerated carbon-carbon bond forming process under these reaction conditions, several enamine substrates were prepared from both isobutyraldehyde and cyclohexanone. Each substrate used in these studies was prepared having an unsymmetrical N-allylic group, substituted with either an alkyl or phenyl substituent at the 4 or 6 position of the 3-aza-Cope framework. In all cam examined, reaction acceleration by the electrophilic reagent produced regiospecific [3,3] rearrangement to the corresponding products resulting from [1,3] rearrangement were not observed. Hydride reduction of the resulting imines generated the delta,epsilon-unsaturated amines in 55-94% overall yield in the three-step condensation-rearrangement-reduction process from the secondary allylamine.

  DOI：

  10.1021/jo00052a037

文献信息

• A one-pot oxidation–imine formation–reduction route from alcohols to amines using manganese dioxide–sodium borohydride: the synthesis of naftifine
  作者：Hisashi Kanno、Richard J.K. Taylor

  DOI：10.1016/s0040-4039(02)01722-7

  日期：2002.10

  A new procedure for the one-pot conversion of alcohols into amines is described which utilises manganese dioxide in the presence of sodium borohydride; the scope of this process is outlined, as is its application to the preparation of the topical antifungal agent, naftifine. (C) 2002 Elsevier Science Ltd. All rights reserved.