(RS)-3-methoxycarbonyl-5-phenyltetronic acid | 522615-22-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: (RS)-3-methoxycarbonyl-5-phenyltetronic acid
• 英文别名: Tzmrrxhttyezgo-uhfffaoysa-；methyl 3-hydroxy-5-oxo-2-phenyl-2H-furan-4-carboxylate
• CAS: 522615-22-1
• 化学式: C₁₂H₁₀O₅
• 分子量: 234.208
• InChiKey: TZMRRXHTTYEZGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  对氯苯胺 、 (RS)-3-methoxycarbonyl-5-phenyltetronic acid 以 甲苯 为溶剂， 反应 1.0h， 生成 N-(4-chlorophenyl)-3-hydroxy-5-oxo-2-phenyl-2H-furan-4-carboxamide
  参考文献：
  名称：

  Design and structure–activity relationships of potent and selective inhibitors of undecaprenyl pyrophosphate synthase (UPPS): Tetramic, tetronic acids and dihydropyridin-2-ones

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.02.009
• 作为产物：
  描述：

  (RS)-2-acetoxyphenylacetic acid 2,5-dioxopyrrolidin-1-yl ester 在 盐酸 、 甲醇 、 sodium hydride 作用下， 以 苯 为溶剂， 反应 29.0h， 生成 (RS)-3-methoxycarbonyl-5-phenyltetronic acid
  参考文献：
  名称：

  由α-羟基酸的新型活性酯合成四氢萘酸衍生物

  摘要：

  由O-乙酰基保护的α-羟基酸与N-羟基琥珀酰亚胺缩合生成的活性酯与活性亚甲基化合物的阴离子反应，生成β，β-三羰基衍生物，脱保护后进行环化生成3-烷氧基羰基和3-酰基tetronic酸。在该反应顺序中并入（S）-2-乙酰氧基苯乙酸能够合成光学活性的5-苯基tetronic酸衍生物。

  DOI：

  10.1002/jhet.5570390614

文献信息

• 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.
• Synthesis of tetronic acid derivatives from novel active esters of α-hydroxyacids
  作者：Christos Mitsos、Alexandras Zografos、Olga Igglessi-Markopoulou

  DOI：10.1002/jhet.5570390614

  日期：2002.11

  Active esters, produced by condensation of O-acetyl protected α-hydroxyacids with N-hydroxysuccin-imide, react with anions of active methylene compounds to afford β,β-tricarbonyl derivatives which upon deprotection undergo cyclization to 3-alkoxycarbonyl and 3-acyl tetronic acids. Incorporation of (S)-2-ace-toxyphenylacetic acid in this reaction sequence enables the synthesis of optically active 5-phenyltetronic

  由O-乙酰基保护的α-羟基酸与N-羟基琥珀酰亚胺缩合生成的活性酯与活性亚甲基化合物的阴离子反应，生成β，β-三羰基衍生物，脱保护后进行环化生成3-烷氧基羰基和3-酰基tetronic酸。在该反应顺序中并入（S）-2-乙酰氧基苯乙酸能够合成光学活性的5-苯基tetronic酸衍生物。

表征谱图