cyanomethyl 3-methyl-4-oxononanoate | 152419-32-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: cyanomethyl 3-methyl-4-oxononanoate
• CAS: 152419-32-4
• 化学式: C₁₂H₁₉NO₃
• 分子量: 225.288
• InChiKey: LIBHUBUILPKXQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• 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：

  cyanomethyl 3-methyl-4-oxononanoate 生成 cyanomethyl (R)-(+)-3-methyl-4-oxononanoate
  参考文献：
  名称：

  Enzymatic resolution of 3-substituted-4-oxoesters.

  摘要：

  The lipase catalyzed hydrolysis of cyanomethyl 3-substituted-4-oxoesters was studied. With 3-methyl substituted esters, PPL led to optically active compounds. When the 3-substituent was a larger group, more satisfactory results were obtained with PL, especially if the substituent attached to the ketone function is other from methyl.

  DOI：

  10.1016/s0957-4166(00)80116-0
• 作为产物：
  描述：

  氯乙腈 、 3-methyl-4-oxononanoic acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到cyanomethyl 3-methyl-4-oxononanoate
  参考文献：
  名称：

  Enzymatic resolution of 3-substituted-4-oxoesters.

  摘要：

  The lipase catalyzed hydrolysis of cyanomethyl 3-substituted-4-oxoesters was studied. With 3-methyl substituted esters, PPL led to optically active compounds. When the 3-substituent was a larger group, more satisfactory results were obtained with PL, especially if the substituent attached to the ketone function is other from methyl.

  DOI：

  10.1016/s0957-4166(00)80116-0

文献信息

• A chemoenzymatic synthesis of optically active aza analogues of Quercus lactones
  作者：Fulvia Felluga、Valentina Gombac、Michela Pavan、Giuliana Pitacco、Ennio Valentin

  DOI：10.1016/j.tetasy.2003.10.014

  日期：2004.1

  The synthesis of optically active 4-methyl-5-n-butyl- and 5-n-pentylpyrrolidin-2-ones, aza analogues of the corresponding Quercus lactones, has been achieved by a chemoenzymatic procedure, involving in the enantiodifferentiating step the enzymatic kinetic resolution of the corresponding γ-ketoester precursors, followed by reductive amination and subsequent cyclization of the enantiomerically pure hydrolysis

  光学活性的4-甲基-5-正丁基和5-正戊基吡咯烷二-2-酮（相应的栎内酯的氮杂类似物）的合成已通过化学酶促方法完成，该化学酶促方法包括在对映异构步骤中进行酶促动力学。拆分相应的γ-酮酸酯前体，然后进行还原胺化，然后将对映体纯水解产物环化。还研究了反应条件的影响以及底物结构对酶水解的影响。