(RS)-(+/-)-N-(2-(methoxycarbonyl)-1-phenylethyl)malonamic acid methyl ester | 656808-19-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (RS)-(+/-)-N-(2-(methoxycarbonyl)-1-phenylethyl)malonamic acid methyl ester
• 英文别名: methyl 3-(2-methoxycarbonylacetylamino)-3-phenylpropanoate；methyl 3-[(3-methoxy-3-oxo-1-phenylpropyl)amino]-3-oxopropanoate；methyl 3-[(3-methoxy-3-oxopropanoyl)amino]-3-phenylpropanoate
• CAS: 656808-19-4
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: OELLNIDKURXXJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (RS)-(+/-)-N-(2-(methoxycarbonyl)-1-phenylethyl)malonamic acid methyl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以70%的产率得到3-methoxycarbonyl-6-phenylpiperidine-2,4-dione
  参考文献：
  名称：

  通过Dieckmann环化反应选择性取代的哌啶-2,4-二酮及其衍生物的区域选择性合成

  摘要：

  描述了一种柔性路线，该路线可得到在6-，5,6-和2,6-位被1和2取代的哌啶-2,4-二酮，无论有无取代。不需要氮保护基。还描述了相关的区域选择性Dieckmann环化反应，该环化反应使用戴维斯的α-甲基苄胺助剂，并选择性地提供6-取代的哌啶-2,4-二酮。

  DOI：

  10.1016/j.tet.2015.06.052
• 作为产物：
  描述：

  monomethyl monopotassium malonate 、 3-苯基-3-氨基丙酸甲酯盐酸盐 在 盐酸 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 水 、 二氯甲烷 为溶剂， 反应 2.0h， 以99%的产率得到(RS)-(+/-)-N-(2-(methoxycarbonyl)-1-phenylethyl)malonamic acid methyl ester
  参考文献：
  名称：

  Carboxamides of Dihydropyridin-2(1 H )-ones

  摘要：

  3-Carboxamides and 3-carboxanilides of 6-alkyl and 6-aryldihydropyridin-2(1H)-ones have been prepared via different reaction pathways. All synthesized amides show hydrogen bonds in their NMR spectra. The 4-hydroxy compounds were obtained as a mixture of tautomers. Their configurations were elucidated by NMR experiments.

  DOI：

  10.1007/s00706-003-0018-0

文献信息

• INHIBITORS OF UNDECAPRENYL PYROPHOSPHATE SYNTHASE
  申请人：Hurley Timothy Brian

  公开号：US20090203694A1

  公开（公告）日：2009-08-13

  The present invention relates to compounds that are selective and/or potent inhibitors of UPPS. In addition to compounds which inhibit UPPS, the invention also provides pharmaceutical compositions comprising these compounds and methods of using these compounds for treating bacterial disease, such as bacterial infection.

  本发明涉及一种选择性和/或强效抑制UPPS的化合物。除了抑制UPPS的化合物外，本发明还提供包含这些化合物的药物组合物以及使用这些化合物治疗细菌性疾病（如细菌感染）的方法。
• WO2008/14311
  申请人：——

  公开号：——

  公开（公告）日：——
• Design and structure–activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones
  作者：Stefan Peukert、Yingchuan Sun、Rui Zhang、Brian Hurley、Mike Sabio、Xiaoyu Shen、Christen Gray、JoAnn Dzink-Fox、Jianshi Tao、Regina Cebula、Sompong Wattanasin

  DOI：10.1016/j.bmcl.2008.02.009

  日期：2008.3

  Based on a pharmacophore hypothesis substituted tetramic and tetronic acid 3-carboxamides as well as dihydropyridin-2-one- 3-carboxamides were investigated as inhibitors of undecaprenyl pyrophosphate synthase (UPPS) for use as novel antimicrobial agents. Synthesis and structure - activity relationship patterns for this class of compounds are discussed. Selectivity data and antibacterial activities for selected compounds are provided. (C) 2008 Elsevier Ltd. All rights reserved.
• Carboxamides of Dihydropyridin-2(1 H )-ones
  作者：Robert Weis、Armin Presser、Werner Seebacher

  DOI：10.1007/s00706-003-0018-0

  日期：2003.8.1

  3-Carboxamides and 3-carboxanilides of 6-alkyl and 6-aryldihydropyridin-2(1H)-ones have been prepared via different reaction pathways. All synthesized amides show hydrogen bonds in their NMR spectra. The 4-hydroxy compounds were obtained as a mixture of tautomers. Their configurations were elucidated by NMR experiments.
• Regioselective synthesis of substituted piperidine-2,4-diones and their derivatives via Dieckmann cyclisations
  作者：Charles M. Marson、Kin Cheung Yau

  DOI：10.1016/j.tet.2015.06.052

  日期：2015.9

  A flexible route to piperidine-2,4-diones variously substituted at the 6-, 5,6- and 2,6-positions, both with and without 1-substitution, is described; no N-protective group is required. A related regioselective Dieckmann cyclisation is also described that uses Davies' α-methylbenzylamine auxiliary and affords 6-substituted piperidine-2,4-diones enantioselectively.

  描述了一种柔性路线，该路线可得到在6-，5,6-和2,6-位被1和2取代的哌啶-2,4-二酮，无论有无取代。不需要氮保护基。还描述了相关的区域选择性Dieckmann环化反应，该环化反应使用戴维斯的α-甲基苄胺助剂，并选择性地提供6-取代的哌啶-2,4-二酮。