(1R,2S)-2-{Allyl-[(S)-1-((E)-styryl)-but-3-enyl]-amino}-1-phenyl-propan-1-ol | 335321-19-2

• 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: (1R,2S)-2-{Allyl-[(S)-1-((E)-styryl)-but-3-enyl]-amino}-1-phenyl-propan-1-ol
• 英文别名: (1R,2S)-1-phenyl-2-[[(1E,3S)-1-phenylhexa-1,5-dien-3-yl]-prop-2-enylamino]propan-1-ol
• CAS: 335321-19-2
• 化学式: C₂₄H₂₉NO
• 分子量: 347.5
• InChiKey: XCPRKZBHCWYJHJ-MVOGYQIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2-{Allyl-[(S)-1-((E)-styryl)-but-3-enyl]-amino}-1-phenyl-propan-1-ol 在 Grubbs catalyst first generation 、 氯化亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 73.0h， 生成 (S)-2-((E)-Styryl)-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：

  去甲麻黄碱 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 (1R,2S)-2-{Allyl-[(S)-1-((E)-styryl)-but-3-enyl]-amino}-1-phenyl-propan-1-ol
  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

• 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.