(S)-N-(1-phenyl-2-propenyl)allylamine | 735334-59-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-N-(1-phenyl-2-propenyl)allylamine
• 英文别名: (1S)-1-phenyl-N-prop-2-enylprop-2-en-1-amine
• CAS: 735334-59-5
• 化学式: C₁₂H₁₅N
• 分子量: 173.258
• InChiKey: WPOJUOFYPXRDPN-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (S)-N-(1-phenyl-2-propenyl)allylamine 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.0h， 生成 (S)-2-Phenyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 2-substituted-N-Boc-Δ-4,5-piperidines

  摘要：

  The title compounds were prepared through a synthetic sequence involving: (i) a reaction of the condensation product between an enantiopure beta -amino alcohol and an aldehyde with allylmagnesium chloride; (ii) an N-allylation of the resulting secondary amine; (iii) a chemoselective cleavage of the beta -amino alcohol residue; and (iv) a protection of the secondary amine followed by a ring closing metathesis. The advantageous use of (1R,2S)-norephedrine was demonstrated in these syntheses. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00462-6
• 作为产物：
  描述：

  在 氯化亚砜 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 72.0h， 生成 (S)-N-(1-phenyl-2-propenyl)allylamine
  参考文献：
  名称：

  Enantioselective synthesis of 2-substituted-N-Boc-Δ-4,5-piperidines

  摘要：

  The title compounds were prepared through a synthetic sequence involving: (i) a reaction of the condensation product between an enantiopure beta -amino alcohol and an aldehyde with allylmagnesium chloride; (ii) an N-allylation of the resulting secondary amine; (iii) a chemoselective cleavage of the beta -amino alcohol residue; and (iv) a protection of the secondary amine followed by a ring closing metathesis. The advantageous use of (1R,2S)-norephedrine was demonstrated in these syntheses. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00462-6

文献信息

• Phosphoramidite Ligands in Iridium-Catalyzed Allylic Substitution
  作者：Damien Polet、Alexandre Alexakis、Karine Tissot-Croset、Clémence Corminboeuf、Klaus Ditrich

  DOI：10.1002/chem.200501180

  日期：2006.4.24

  A new phosphoramidite ligand was used in the iridium-catalyzed allylic substitution reaction. This permitted high regio- and enantioselectivities on a wide variety of substrates and nucleophiles. Because of the stereospecificity of the reaction obtained by using branched substrates, a kinetic resolution reaction was attempted. The origin of the impressive efficiency of this ligand in terms of kinetics

  在铱催化的烯丙基取代反应中使用了新的亚磷酰胺配体。这允许在多种底物和亲核试剂上具有很高的区域和对映选择性。由于通过使用支链底物获得的反应的立体特异性，尝试进行动力学拆分反应。详细研究了该配体在动力学方面令人印象深刻的效率的起因，以及取代基在胺部分邻位中的作用。
• Enantioselective synthesis of 2-substituted-N-Boc-Δ-4,5-piperidines
  作者：Claude Agami、François Couty、Gwilherm Evano

  DOI：10.1016/s0957-4166(00)00462-6

  日期：2000.12

  The title compounds were prepared through a synthetic sequence involving: (i) a reaction of the condensation product between an enantiopure beta -amino alcohol and an aldehyde with allylmagnesium chloride; (ii) an N-allylation of the resulting secondary amine; (iii) a chemoselective cleavage of the beta -amino alcohol residue; and (iv) a protection of the secondary amine followed by a ring closing metathesis. The advantageous use of (1R,2S)-norephedrine was demonstrated in these syntheses. (C) 2001 Elsevier Science Ltd. All rights reserved.