Phenethyl-(1-propyl-pentyl)-amine | 90496-18-7

• 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: Phenethyl-(1-propyl-pentyl)-amine
• 英文别名: N-(2-phenylethyl)octan-4-amine
• CAS: 90496-18-7
• 化学式: C₁₆H₂₇N
• 分子量: 233.397
• InChiKey: PIBDUQCEMMRJHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.625
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Phenethyl-[1-propyl-pent-(E)-ylidene]-amine 在 sodium cyanoborohydride 、 zinc(II) chloride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 20.0h， 以456 mg的产率得到Phenethyl-(1-propyl-pentyl)-amine
  参考文献：
  名称：

  Cp*₂TiMe₂:  An Improved Catalyst for the Intermolecular Addition of n-Alkyl- and Benzylamines to Alkynes

  摘要：

  Cp*2TiMe2 has been found to be a competent catalyst for the intermolecular addition of sterically less demanding n-alkyl- and benzylamines to internal alkynes. In the presence of 2.0-6.0 mol % of the catalyst, hydroamination reactions between n-propyl-, n-hexyl-, benzyl-, p-methoxybenzyl- or 2-phenylethylamine and diphenylacetylene, 3-hexyne or 4-octyne go to completion within 24 h or less at 114 degreesC (oil bath temperature). After subsequent reduction of the initially formed imines with zinc-modified sodium cyanoborohydride in MeOH at 25 degreesC, the corresponding secondary amines can be isolated in excellent yields (>78%). Hydroamination/reduction sequences employing the unsymmetrically substituted alkyne 1-phenylpropyne give access to mixtures of regioisomeric secondary amines. The observed regioselectivity is low.

  DOI：

  10.1021/jo016311p

文献信息

• Addition of boron trifluoride complexes of organocopper reagentsto aldimines containing α-hydrogens
  作者：Makoto Wada、Yōji Sakurai、Kin-ya Akiba

  DOI：10.1016/s0040-4039(01)80106-4

  日期：1984.1

  RCu · BF3, generated in situ from Grignard reagents, CuI, and BF3 · OEt2, added to aldimines containing α-hydrogens to afford secondary amines in good yields. Boron trifluoride complex of dialkylcuprate gave essentially the same result with wider application.

  由Grignard试剂CuI和BF 3 ·OEt 2原位生成的RCu·BF 3加入到含有α氢的醛亚胺中，以高收率得到仲胺。三烷基硼酸酯的三氟化硼配合物在更广泛的应用中获得了基本相同的结果。
• WADA, MAKOTO;SAKURAI, YOJI;AKIBA, KIN-YA, TETRAHEDRON LETT., 1984, 25, N 10, 1079-1082
  作者：WADA, MAKOTO、SAKURAI, YOJI、AKIBA, KIN-YA

  DOI：——

  日期：——
• Cp*₂TiMe₂:  An Improved Catalyst for the Intermolecular Addition of <i>n</i>-Alkyl- and Benzylamines to Alkynes
  作者：Andreas Heutling、Sven Doye

  DOI：10.1021/jo016311p

  日期：2002.3.1

  Cp*2TiMe2 has been found to be a competent catalyst for the intermolecular addition of sterically less demanding n-alkyl- and benzylamines to internal alkynes. In the presence of 2.0-6.0 mol % of the catalyst, hydroamination reactions between n-propyl-, n-hexyl-, benzyl-, p-methoxybenzyl- or 2-phenylethylamine and diphenylacetylene, 3-hexyne or 4-octyne go to completion within 24 h or less at 114 degreesC (oil bath temperature). After subsequent reduction of the initially formed imines with zinc-modified sodium cyanoborohydride in MeOH at 25 degreesC, the corresponding secondary amines can be isolated in excellent yields (>78%). Hydroamination/reduction sequences employing the unsymmetrically substituted alkyne 1-phenylpropyne give access to mixtures of regioisomeric secondary amines. The observed regioselectivity is low.