3-((R)-1-Azido-but-3-enyl)-pyridine | 326818-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-((R)-1-Azido-but-3-enyl)-pyridine
• 英文别名: 3-[(1R)-1-azidobut-3-enyl]pyridine
• CAS: 326818-54-6
• 化学式: C₉H₁₀N₄
• 分子量: 174.205
• InChiKey: BJRTWPRANJXHOM-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  27.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((R)-1-Azido-but-3-enyl)-pyridine 在 lithium aluminium tetrahydride 、 bis(cyclohexanyl)borane 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 12.0h， 生成 D-(+)-尼古丁
  参考文献：
  名称：

  A short and efficient synthesis of unnatural (R)-nicotine

  摘要：

  A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01675-0
• 作为产物：
  描述：

  (1S)-1-(3-吡啶基)-3-丁烯-1-醇 在 叠氮磷酸二苯酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 以90%的产率得到3-((R)-1-Azido-but-3-enyl)-pyridine
  参考文献：
  名称：

  A short and efficient synthesis of unnatural (R)-nicotine

  摘要：

  A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01675-0

文献信息

• Felpin; Vo-Thanh; Robins, Synlett, 2000, # 11, p. 1646 - 1648
  作者：Felpin、Vo-Thanh、Robins、Villieras、Lebreton

  DOI：——

  日期：——
• A short and efficient synthesis of unnatural (R)-nicotine
  作者：Sandrine Girard、Richard J Robins、Jean Villiéras、Jacques Lebreton

  DOI：10.1016/s0040-4039(00)01675-0

  日期：2000.11

  A short and efficient synthesis of unnatural (R)-nicotine is described, in which the key step is an intramolecular hydroboration-cycloalkylation of an azido-olefin intermediate. The synthesis is achieved in only four steps, with an overall yield of 51% (or in six steps with an overall yield of 65%). (C) 2000 Elsevier Science Ltd. All rights reserved.