benzyl N-[1-(4-cyanophenyl)pent-4-en-2-yl]carbamate | 187974-81-8

• 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: benzyl N-[1-(4-cyanophenyl)pent-4-en-2-yl]carbamate
• CAS: 187974-81-8
• 化学式: C₂₀H₂₀N₂O₂
• 分子量: 320.391
• InChiKey: PKVFFQJGKZOYKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl N-[1-(4-cyanophenyl)pent-4-en-2-yl]carbamate 在 sodium hydroxide 、 三甲基氯硅烷 、 三氟甲磺酸 、 苄基三丁基氯化铵 、 碳酸氢钠 、 sodium iodide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 N-[(2S,4R)-2-(4-Cyano-benzyl)-1-(3,5-dimethyl-benzoyl)-piperidin-4-yl]-acetamide
  参考文献：
  名称：

  SAR of 2-benzyl-4-aminopiperidines NK1 antagonists. Part 21. synthesis of CGP 49823

  摘要：

  CGP 49823 is a potent NK1 antagonist which is centrally active after oral administration. The SAR of the C-2 substituent was investigated with respect to the affinity to the NK1 receptor. A practical synthesis of CGP 49823, suitable for scale-up, was developed. The key-step, a tandem acyliminium ion cyclization / Ritter reaction, gave trans 2-benzyl-4-acetamido-piperidines with high diastereoselectivity. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00563-x
• 作为产物：
  描述：

  氨基甲酸苄酯 、 4-(2,2-Dimethoxy-ethyl)-benzonitrile 、 烯丙基三甲基硅烷 在 三氟化硼乙醚 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以71%的产率得到benzyl N-[1-(4-cyanophenyl)pent-4-en-2-yl]carbamate
  参考文献：
  名称：

  One-pot synthesis of protected homoallyl amines

  摘要：

  An efficient one-pot procedure for the synthesis of protected homoallyl amines from aldehydes or aldehyde acetals, carbamates and allyltrimethylsilane under influence of borontrifluoride etherate was developed. Scope and limitations of the aldehyde and carbamate components are reported. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(96)02458-6

文献信息

• SAR of 2-benzyl-4-aminopiperidines NK1 antagonists. Part 21. synthesis of CGP 49823
  作者：Siem J. Veenstra、Kathleen Hauser、Walter Schilling、Claudia Betschart、Silvio Ofner

  DOI：10.1016/s0960-894x(96)00563-x

  日期：1996.12

  CGP 49823 is a potent NK1 antagonist which is centrally active after oral administration. The SAR of the C-2 substituent was investigated with respect to the affinity to the NK1 receptor. A practical synthesis of CGP 49823, suitable for scale-up, was developed. The key-step, a tandem acyliminium ion cyclization / Ritter reaction, gave trans 2-benzyl-4-acetamido-piperidines with high diastereoselectivity. Copyright (C) 1996 Elsevier Science Ltd
• One-pot synthesis of protected homoallyl amines
  作者：Siem J. Veenstra、Priska Schmid

  DOI：10.1016/s0040-4039(96)02458-6

  日期：1997.2

  An efficient one-pot procedure for the synthesis of protected homoallyl amines from aldehydes or aldehyde acetals, carbamates and allyltrimethylsilane under influence of borontrifluoride etherate was developed. Scope and limitations of the aldehyde and carbamate components are reported. (C) 1997, Elsevier Science Ltd.