ethyl (1R)-1-(2-cyanoethyl)-2-oxocyclohexane-1-carboxylate | 152614-57-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (1R)-1-(2-cyanoethyl)-2-oxocyclohexane-1-carboxylate
• CAS: 152614-57-8
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: JPLIBLZLHLCMQS-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (1R)-1-(2-cyanoethyl)-2-oxocyclohexane-1-carboxylate 在 platinum(IV) oxide sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氢气 作用下， 以 甲醇 为溶剂， 反应 17.0h， 生成 (-)-isonitramine
  参考文献：
  名称：

  Ple-catalyzed resolution of α-substituted β-ketoesters application to the synthesis of (+)-nitraniine and (−)-Isonitramine

  摘要：

  Substituted beta-Ketoesters can be prepared in enantiomerically pure form by pig liver esterase catalyzed hydrolysis of their racemic precursors. With the asymmetric carbon atom possessing a quaternary centre, (+)-Nitramine and (-)-Isonitramine have been synthesized.

  DOI：

  10.1016/s0957-4166(00)80054-3
• 作为产物：
  描述：

  ethyl 1-(2-cyanoethyl)-2-oxocyclohexanecarboxylate 生成 ethyl (1R)-1-(2-cyanoethyl)-2-oxocyclohexane-1-carboxylate
  参考文献：
  名称：

  Ple-catalyzed resolution of α-substituted β-ketoesters application to the synthesis of (+)-nitraniine and (−)-Isonitramine

  摘要：

  Substituted beta-Ketoesters can be prepared in enantiomerically pure form by pig liver esterase catalyzed hydrolysis of their racemic precursors. With the asymmetric carbon atom possessing a quaternary centre, (+)-Nitramine and (-)-Isonitramine have been synthesized.

  DOI：

  10.1016/s0957-4166(00)80054-3

文献信息

• Asymmetric nucleophilic addition of chiral β - enamino esters to acrylonitrile
  作者：André Guingant、Hedi Hammami

  DOI：10.1016/s0957-4166(00)86008-5

  日期：1993.1

  β - enamino esters derived from β - keto esters and (S)-1- phenylethytamine, react with acrylonitrile in the presence of a Lewis acid or under high pressure activation to give, after hydrolytic work up, α,α- disubstituted β - keto esters 4 (EWG=CN) in enantiomeric excesses close lo 90%.

  衍生自β-酮酸酯和（S）-1-苯乙胺的β-烯胺酯在路易斯酸存在下或在高压活化下与丙烯腈反应，经水解后得到α，α-二取代的β-酮对映体过量的酯4（EWG ＝ CN）接近90％。
• Ple-catalyzed resolution of α-substituted β-ketoesters application to the synthesis of (+)-nitraniine and (−)-Isonitramine
  作者：Bernhard Westermann、Hildegard Große Scharmann、Ina Kortmann

  DOI：10.1016/s0957-4166(00)80054-3

  日期：1993.10

  Substituted beta-Ketoesters can be prepared in enantiomerically pure form by pig liver esterase catalyzed hydrolysis of their racemic precursors. With the asymmetric carbon atom possessing a quaternary centre, (+)-Nitramine and (-)-Isonitramine have been synthesized.