ethyl 3-cyano-7-hydroxy-4-phenyl-7-azabicyclo[2.2.1]heptane-1-carboxylate

• 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: ethyl 3-cyano-7-hydroxy-4-phenyl-7-azabicyclo[2.2.1]heptane-1-carboxylate
• 化学式: C₁₆H₁₈N₂O₃
• 分子量: 286.331
• InChiKey: SYLBABIYTNNKNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吖啶橙 在 palladium on activated charcoal sodium tungstate 、 urea hydrogen peroxide 、 氢气 、 sodium hydride 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， 10.0~20.0 ℃ 、101.33 kPa 条件下， 反应 11.5h， 生成 ethyl 3-cyano-7-hydroxy-4-phenyl-7-azabicyclo[2.2.1]heptane-1-carboxylate
  参考文献：
  名称：

  Synthesis and Reactivity of 1-Pyrroline-5-carboxylate Ester 1-Oxides

  摘要：

  Some C5 mono- and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding gamma-nitro carbonyl compounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselectively alkylated at C5. Acylation of this molecule occurs exclusively on the nitrone oxygen and leads to C3 substituted pyrrolines as the result of a hetero-Cope rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00094-6

文献信息

• Synthesis and Reactivity of 1-Pyrroline-5-carboxylate Ester 1-Oxides
  作者：David StC. Black、Gavin L. Edwards、Richard H. Evans、Paul A. Keller、Sean M. Laaman

  DOI：10.1016/s0040-4020(00)00094-6

  日期：2000.3

  Some C5 mono- and diester-substituted 1-pyrroline-1-oxides have been prepared via reductive cyclisation of the corresponding gamma-nitro carbonyl compounds. Ethyl 2-phenyl-1-pyrroline-1-oxide-5-carboxylate 5c was regioselectively alkylated at C5. Acylation of this molecule occurs exclusively on the nitrone oxygen and leads to C3 substituted pyrrolines as the result of a hetero-Cope rearrangement. (C) 2000 Elsevier Science Ltd. All rights reserved.