methyl 1-benzyl-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate | 1208236-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: methyl 1-benzyl-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate
• 英文别名: methyl N-benzyl-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate
• CAS: 1208236-34-3
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: JROVCOGHMSMBHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.57
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 1-benzyl-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以100%的产率得到N-benzyl-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Substituted aryl malonamates as new serine β-lactamase substrates: Structure–activity studies

  摘要：

  A series of substituted aryl malonamates have been prepared. These compounds are analogues of aryl phenaceturates where the amido side chain has been replaced by a retro-amide. Like the phenaceturates, these compounds are substrates of typical class A and class C beta-lactamases, particularly of the latter, and of soluble DD-peptidases. The effect of substituents alpha to the ester carbonyl group on turnover by these enzymes is similar to that in the phenaceturates. On the other hand, N-alkylation of the side chain amide of malonamates, but not of phenaceturates, retains the susceptibility of the compounds to hydrolysis by beta-lactamases. This reactivity is not enhanced, however, by bridging the amide nitrogen and C alpha atoms. A phosphonate analogue of the malonamates was found to be an irreversible inhibitor of the beta-lactamases. These results, therefore, provide further evidence for the covalent access of compounds bearing retroamide side chains to the active sites of beta-lactam-recognizing enzymes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.056
• 作为产物：
  描述：

  methyl N-benzyl-3-tert-butoxycarbonyl-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以93%的产率得到methyl 1-benzyl-2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate
  参考文献：
  名称：

  Substituted aryl malonamates as new serine β-lactamase substrates: Structure–activity studies

  摘要：

  A series of substituted aryl malonamates have been prepared. These compounds are analogues of aryl phenaceturates where the amido side chain has been replaced by a retro-amide. Like the phenaceturates, these compounds are substrates of typical class A and class C beta-lactamases, particularly of the latter, and of soluble DD-peptidases. The effect of substituents alpha to the ester carbonyl group on turnover by these enzymes is similar to that in the phenaceturates. On the other hand, N-alkylation of the side chain amide of malonamates, but not of phenaceturates, retains the susceptibility of the compounds to hydrolysis by beta-lactamases. This reactivity is not enhanced, however, by bridging the amide nitrogen and C alpha atoms. A phosphonate analogue of the malonamates was found to be an irreversible inhibitor of the beta-lactamases. These results, therefore, provide further evidence for the covalent access of compounds bearing retroamide side chains to the active sites of beta-lactam-recognizing enzymes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.056

文献信息

• Air- and Light-Stable <i>S</i>-(Difluoromethyl)sulfonium Salts: <i>C</i>-Selective Electrophilic Difluoromethylation of β-Ketoesters and Malonates
  作者：Sheng-Le Lu、Xin Li、Wen-Bing Qin、Jian-Jian Liu、Yi-Yong Huang、Henry N. C. Wong、Guo-Kai Liu

  DOI：10.1021/acs.orglett.8b03067

  日期：2018.11.2

  Air- and light-stable electrophilic difluoromethylating reagents, S-(difluoromethyl)-S-phenyl-S-(2,4,6-trialkoxyphenyl) sulfonium salts were successfully developed, and the introduction of intramolecular hydrogen bonds plays a crucial role for the stabilities and reactivities of these reagents. C-selective difluoromethylation of a broad range of β-ketoesters and malonates proceeded smoothly under mild

  空气和光稳定的亲电子二氟甲基化试剂，S-（二氟甲基）-S-苯基-S-（2,4,6-三烷氧基苯基）salts盐已成功开发，并且分子内氢键的引入对于该化合物起着至关重要的作用。这些试剂的稳定性和反应性。在温和的反应条件下，各种β-酮酸酯和丙二酸酯的C选择性二氟甲基化反应平稳进行，从而以良好的C / O区域选择性提供了良好至优异的收率。