endo-ethyl 1-azabicyclo[2.2.1]heptane-2-carboxylate | 921755-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: endo-ethyl 1-azabicyclo[2.2.1]heptane-2-carboxylate
• 英文别名: ethyl (2R,4R)-1-azabicyclo[2.2.1]heptane-2-carboxylate
• CAS: 921755-44-4
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: VOTUVXPAUKQGFP-HTQZYQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  endo-ethyl 1-azabicyclo[2.2.1]heptane-2-carboxylate 在 盐酸 作用下， 生成 endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid hydrochloride
  参考文献：
  名称：

  Synthesis of Bicyclic Tertiary α-Amino Acids

  摘要：

  Novel bicyclic alpha-amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generation of neuronal nicotinic receptor ligands. Alkylation of glycine-derived Schiff bases or nitroacetates with cyclic ether electrophiles, followed by acid-induced ring opening and cyclization in NH4OH, allowed for the preparation of substantial quantities of the three tertiary bicyclic alpha-amino acids.

  DOI：

  10.1021/jo061977a
• 作为产物：
  描述：

  (tetrahydrofuran-3-yl)methyl methanesulfonate 在 ammonium hydroxide 、 硫酸 、 氢溴酸 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 20.5h， 生成 endo-ethyl 1-azabicyclo[2.2.1]heptane-2-carboxylate
  参考文献：
  名称：

  Synthesis of Bicyclic Tertiary α-Amino Acids

  摘要：

  Novel bicyclic alpha-amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generation of neuronal nicotinic receptor ligands. Alkylation of glycine-derived Schiff bases or nitroacetates with cyclic ether electrophiles, followed by acid-induced ring opening and cyclization in NH4OH, allowed for the preparation of substantial quantities of the three tertiary bicyclic alpha-amino acids.

  DOI：

  10.1021/jo061977a

文献信息

• Synthesis of Bicyclic Tertiary α-Amino Acids
  作者：Jon-Paul Strachan、Regina C. Whitaker、Craig H. Miller、Balwinder S. Bhatti

  DOI：10.1021/jo061977a

  日期：2006.12.1

  Novel bicyclic alpha-amino acids, exo and endo-1-azabicyclo[2.2.1]heptane-2-carboxylic acid, 1-azabicyclo[2.2.1]heptane-7-carboxylic acid, and 1-azabicyclo[3.2.2]nonane-2-carboxylic acid have been readily synthesized for the generation of neuronal nicotinic receptor ligands. Alkylation of glycine-derived Schiff bases or nitroacetates with cyclic ether electrophiles, followed by acid-induced ring opening and cyclization in NH4OH, allowed for the preparation of substantial quantities of the three tertiary bicyclic alpha-amino acids.