dimethyl α-methyl-α-(2-naphthyl)malonate | 153742-11-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dimethyl α-methyl-α-(2-naphthyl)malonate
• 英文别名: dimethyl α-metyl-α-(2-naphthyl)malonate；dimethyl 2-methyl-(2-naphthyl) malonate；Dimethyl alpha-methyl-alpha-(beta-naphthyl)malonate；dimethyl 2-methyl-2-naphthalen-2-ylpropanedioate
• CAS: 153742-11-1
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: XZYVEWXVLRVGND-UHFFFAOYSA-N

物化性质

• 沸点：
  378.6±22.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl α-methyl-α-(2-naphthyl)malonate 在 sodium hydroxide 作用下， 反应 36.0h， 以95%的产率得到
  参考文献：
  名称：

  Enzymes in organic synthesis 51. Probing the dimensions of the large hydrophobic pocket of the active site of pig liver esterase

  摘要：

  The dimensions of the large hydrophobic pocket (H(L)) of the active site model of pig liver esterase (PLE) were probed using a series of aliphatic and phenylic malonates. Results from the hydrolyses of these new unnatural substrates permitted the extension of the H(L) pocket to give the new dimensions of 6.2 x 2.3 x 3.9 angstrom for a total volume of approximately 56 angstrom3.

  DOI：

  10.1016/s0957-4166(00)82251-x
• 作为产物：
  描述：

  2-萘甲醇 在 盐酸 、 水 、 氢溴酸 、 sodium amide 、 lithium diisopropyl amide 作用下， 以 乙醇 、 水 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 dimethyl α-methyl-α-(2-naphthyl)malonate
  参考文献：
  名称：

  Enzymes in organic synthesis 51. Probing the dimensions of the large hydrophobic pocket of the active site of pig liver esterase

  摘要：

  The dimensions of the large hydrophobic pocket (H(L)) of the active site model of pig liver esterase (PLE) were probed using a series of aliphatic and phenylic malonates. Results from the hydrolyses of these new unnatural substrates permitted the extension of the H(L) pocket to give the new dimensions of 6.2 x 2.3 x 3.9 angstrom for a total volume of approximately 56 angstrom3.

  DOI：

  10.1016/s0957-4166(00)82251-x

文献信息

• Introduction of single mutation changes arylmalonate decarboxylase to racemase
  作者：Yosuke Terao、Kenji Miyamoto、Hiromichi Ohta

  DOI：10.1039/b607211a

  日期：——

  The introduction of only one mutation based on the estimated reaction mechanism endowed arylmalonate decarboxylase with a racemase activity, which catalyses racemisation of alpha-arylpropionates.

  基于估计的反应机理仅引入一种突变赋予芳基丙二酸酯脱羧酶具有消旋酶活性，其催化α-芳基丙酸酯的消旋化。
• Inversion of enantioselectivity of asymmetric biocatalytic decarboxylation by site-directed mutagenesis based on the reaction mechanism
  作者：Yoichiro Ijima、Kaori Matoishi、Yosuke Terao、Nobuhide Doi、Hiroshi Yanagawa、Hiromichi Ohta

  DOI：10.1039/b416398b

  日期：——

  The introduction of two mutations (G74C/C188S) based on the estimated reaction mechanism resulted in the inversion of enantioselectivity of arylmalonate decarboxylase, which catalyses the asymmetric decarboxylation of arylmethylmalonate to give optically active arylpropionate.

  基于估计的反应机理引入两个突变（G74C / C188S）导致芳基丙二酸脱羧酶的对映选择性反转，这催化了芳基丙二酸芳基酯的不对称脱羧，得到了光学活性的芳基丙酸酯。
• Enzymes in organic synthesis 51. Probing the dimensions of the large hydrophobic pocket of the active site of pig liver esterase
  作者：Louis Provencher、Hla Wynn、J.Bryan Jones、Andrzej R. Krawczyk

  DOI：10.1016/s0957-4166(00)82251-x

  日期：1993.1

  The dimensions of the large hydrophobic pocket (H(L)) of the active site model of pig liver esterase (PLE) were probed using a series of aliphatic and phenylic malonates. Results from the hydrolyses of these new unnatural substrates permitted the extension of the H(L) pocket to give the new dimensions of 6.2 x 2.3 x 3.9 angstrom for a total volume of approximately 56 angstrom3.