ethyl (S)-(-)-3-methyl-3-(nitromethyl)heptanoate | 1250909-57-9

• 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 (S)-(-)-3-methyl-3-(nitromethyl)heptanoate
• 英文别名: ethyl (3S)-3-methyl-3-(nitromethyl)heptanoate
• CAS: 1250909-57-9
• 化学式: C₁₁H₂₁NO₄
• 分子量: 231.292
• InChiKey: AYXFCOHQUOLBGM-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (S)-(-)-3-methyl-3-(nitromethyl)heptanoate 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (S)-2-butyl-2-methylsuccinic acid
  参考文献：
  名称：

  Esterase-mediated synthesis of optically active GABA analogues containing a stereogenic all-carbon quaternary carbon atom

  摘要：

  Esterase from Horse Liver (HLAP) was able to hydrolyze a series of linear and cyclic beta,beta-dialkyl-gamma-nitroesters, in spite of the well-known reluctance of hydrolytic enzymes to recognize and transform hindered substrates, such as those possessing a stereogenic quaternary carbon atom next to the reaction site. The resulting optically active gamma-nitroesters gave access to optically active beta,beta-disubstituted gamma-aminoacids as well as alpha,alpha-disubstituted succinic acids, both being biologically relevant compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.010
• 作为产物：
  描述：

  ethyl (+/-)-3-methyl-3-(nitromethyl)heptanoate 在 Horse Liver Acetone Powder 作用下， 生成 (R)-(+)-3-methyl-3-(nitromethyl)heptanoic acid 、 (S)-3-methyl-3-(nitromethyl)heptanoic acid 、 ethyl (S)-(-)-3-methyl-3-(nitromethyl)heptanoate 、 ethyl (R)-3-methyl-3-(nitromethyl)heptanoate
  参考文献：
  名称：

  Esterase-mediated synthesis of optically active GABA analogues containing a stereogenic all-carbon quaternary carbon atom

  摘要：

  Esterase from Horse Liver (HLAP) was able to hydrolyze a series of linear and cyclic beta,beta-dialkyl-gamma-nitroesters, in spite of the well-known reluctance of hydrolytic enzymes to recognize and transform hindered substrates, such as those possessing a stereogenic quaternary carbon atom next to the reaction site. The resulting optically active gamma-nitroesters gave access to optically active beta,beta-disubstituted gamma-aminoacids as well as alpha,alpha-disubstituted succinic acids, both being biologically relevant compounds. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.07.010

文献信息

• Esterase-mediated synthesis of optically active GABA analogues containing a stereogenic all-carbon quaternary carbon atom
  作者：Fulvia Felluga、Franco Ghelfi、Giuliana Pitacco、Fabrizio Roncaglia、Ennio Valentin、Cesare Daniele Venneri

  DOI：10.1016/j.tetasy.2010.07.010

  日期：2010.9

  Esterase from Horse Liver (HLAP) was able to hydrolyze a series of linear and cyclic beta,beta-dialkyl-gamma-nitroesters, in spite of the well-known reluctance of hydrolytic enzymes to recognize and transform hindered substrates, such as those possessing a stereogenic quaternary carbon atom next to the reaction site. The resulting optically active gamma-nitroesters gave access to optically active beta,beta-disubstituted gamma-aminoacids as well as alpha,alpha-disubstituted succinic acids, both being biologically relevant compounds. (C) 2010 Elsevier Ltd. All rights reserved.