dimethyl 2-methyl-2-(5-methyl-2-nitrophenoxy)propanedioate | 188407-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2-methyl-2-(5-methyl-2-nitrophenoxy)propanedioate
• CAS: 188407-73-0
• 化学式: C₁₃H₁₅NO₇
• 分子量: 297.265
• InChiKey: KCPRQSFZOUDICU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104.97
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2-methyl-2-(5-methyl-2-nitrophenoxy)propanedioate 在 palladium on activated charcoal sodium hydroxide 、 phosphate buffer 、 pig liver esterase 、 氢气 作用下， 以 1,4-二氧六环 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 72.0h， 生成 (R)-(-)-2,7-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
  参考文献：
  名称：

  Stereoselective synthesis of (R)- and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acids, -carboxylates and -carboxamides

  摘要：

  (R)-Monomethyl 2-methyl-2-(2- nitrophenoxy)malonates obtained by PLE catalyzed hydrolysis of the corresponding dimethyl malonates undergo solvent-dependent enantioselective cyclization to afford (R)-methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-hentoxazine-2-carboxylates and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxyIic acids, respectively. These compounds are easily converted to enantiomerically and diastereomerically pure carboxamides, which are used as peptidomimetic building blocks. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00485-6
• 作为产物：
  描述：

  甲基丙二酸二甲酯 在 potassium fluoride 、 溴 作用下， 反应 7.25h， 生成 dimethyl 2-methyl-2-(5-methyl-2-nitrophenoxy)propanedioate
  参考文献：
  名称：

  猪肝酯酶催化2-甲基-2-（邻硝基苯氧基）丙二酸二甲酯和二乙酯的水解

  摘要：

  猪肝酯酶（PLE）催化2-甲基-2-（邻硝基苯氧基）丙二酸二甲酯和二乙基酯的水解，得到中等至良好对映体过量的（R）-单乙基/单甲基2-甲基-2-（邻硝基苯氧基）丙二酸酯（69–81％）。这些数据表明，硝基可能被容纳在PLE的Jones活性位点模型的较大疏水口袋中。

  DOI：

  10.1016/s0957-4166(96)00535-6

文献信息

• Pig liver esterase catalyzed hydrolysis of dimethyl and diethyl 2-methyl-2-(o-nitrophenoxy)malonates
  作者：Matej Breznik、Danijel Kikelj

  DOI：10.1016/s0957-4166(96)00535-6

  日期：1997.2

  Pig liver esterase (PLE) catalyzed hydrolysis of dimethyl and diethyl 2-methyl-2-(o-nitrophenoxy)malonates affords (R)-monoethyl/monomethyl 2-methyl-2-(o-nitrophenoxy)malonates in moderate to good enantiomeric excesses (69–81 %). These data indicate that the nitro group may be accommodated in the large hydrophobic pocket of the Jones active-site model of PLE.

  猪肝酯酶（PLE）催化2-甲基-2-（邻硝基苯氧基）丙二酸二甲酯和二乙基酯的水解，得到中等至良好对映体过量的（R）-单乙基/单甲基2-甲基-2-（邻硝基苯氧基）丙二酸酯（69–81％）。这些数据表明，硝基可能被容纳在PLE的Jones活性位点模型的较大疏水口袋中。
• Stereoselective synthesis of (R)- and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acids, -carboxylates and -carboxamides
  作者：Matej Breznik、Valentina Hrast、Alenka Mrcina、Danijel Kikelj

  DOI：10.1016/s0957-4166(98)00485-6

  日期：1999.1

  (R)-Monomethyl 2-methyl-2-(2- nitrophenoxy)malonates obtained by PLE catalyzed hydrolysis of the corresponding dimethyl malonates undergo solvent-dependent enantioselective cyclization to afford (R)-methyl 2-methyl-3-oxo-3,4-dihydro-2H-1,4-hentoxazine-2-carboxylates and (S)-2-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxyIic acids, respectively. These compounds are easily converted to enantiomerically and diastereomerically pure carboxamides, which are used as peptidomimetic building blocks. (C) 1999 Elsevier Science Ltd. All rights reserved.