3-carbethoxy-6-(1-methylethyl)-4(1H)-pyridinone | 134653-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-carbethoxy-6-(1-methylethyl)-4(1H)-pyridinone
• 英文别名: Ethyl 6-(1-methylethyl)-4-oxo-1,4-dihydropyridine-3-carboxylate；ethyl 4-oxo-6-propan-2-yl-1H-pyridine-3-carboxylate
• CAS: 134653-84-2
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: ZIHYHYKUSNHKAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-carbethoxy-6-(1-methylethyl)-4(1H)-pyridinone 在 三氯氧磷 、 乙酸乙酯 、 Brine 、 Sodium sulfate-III 、 异丙醇 、 3-甲氧基丙胺 、 三乙胺 、 碳酸氢钠 、 溶剂黄146 作用下， 以 三氯氧磷 为溶剂， 反应 18.0h， 以to give the object compound (263 mg)的产率得到Ethyl 4-[(3-methoxypropyl)amino]-6-(1-methylethyl)pyridine-3-carboxylate
  参考文献：
  名称：

  AMIDE COMPOUNDS AND USE OF THE SAME

  摘要：

  一种肾素抑制剂，包括一种由下式表示的化合物：其中每个符号如说明书中所定义，或其盐或前药。本发明的化合物具有优异的肾素抑制活性，因此可用作预防或治疗高血压、由高血压引起的各种器官损伤等的药剂。

  公开号：

  US20100324010A1
• 作为产物：
  描述：

  ethyl (Z)-2-((dimethylamino)methylene)-3-oxobutanoate 、 异丁酰氯 在 正丁基锂 、 ammonium acetate 、 溶剂黄146 、 六甲基二硅氮烷 作用下， 以23%的产率得到3-carbethoxy-6-(1-methylethyl)-4(1H)-pyridinone
  参考文献：
  名称：

  Generation and in situ acylation of enaminone anions: a convenient synthesis of 3-carbethoxy-4(1H)-pyridinones and -4-pyrones and related compounds

  摘要：

  Treatment of 2-[(dimethylamino)methylene]-3-oxobutanoates 9 or 10 with LiN(SiMe3)2 in the presence of RCOCl results in C-acylation. The resulting intermediate, without isolation, may be converted to 6-R 3-Carbethoxy-4-pyrones (e.g., 12) by H3O+ or to the corresponding pyridinones (e.g., 13) by NH4OAc. Typically, yields are 55-75% for R groups lacking acidic alpha or gamma protons and ca. 30% for R = Me2CH or MeCH = CH. Replacing 9 with MeCOC(= CHNMe2)SCH2Ph (from MeCOCH2SCH2Ph and Me2NCH(OMe)2 similarly affords 3(PhCH2S)-substituted products such as 29. Alkylation of the pyridinone anions produces mixtures of N- and O-substituted compounds, with the latter predominating; aminolysis of the isolated pyrones (R'NH2-HOAc, where R' = alkyl, Ar, HO, etc.) is the preferred route to the 1-R'-substituted pyridinones.

  DOI：

  10.1021/jo00016a028

文献信息

• AMIDE COMPOUNDS AND USE OF THE SAME
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP2202228B1

  公开（公告）日：2014-12-10
• US8329691B2
  申请人：——

  公开号：US8329691B2

  公开（公告）日：2012-12-11
• Generation and in situ acylation of enaminone anions: a convenient synthesis of 3-carbethoxy-4(1H)-pyridinones and -4-pyrones and related compounds
  作者：Stuart W. McCombie、William A. Metz、Dennis Nazareno、Bandarpalle B. Shankar、Jayaram Tagat

  DOI：10.1021/jo00016a028

  日期：1991.8

  Treatment of 2-[(dimethylamino)methylene]-3-oxobutanoates 9 or 10 with LiN(SiMe3)2 in the presence of RCOCl results in C-acylation. The resulting intermediate, without isolation, may be converted to 6-R 3-Carbethoxy-4-pyrones (e.g., 12) by H3O+ or to the corresponding pyridinones (e.g., 13) by NH4OAc. Typically, yields are 55-75% for R groups lacking acidic alpha or gamma protons and ca. 30% for R = Me2CH or MeCH = CH. Replacing 9 with MeCOC(= CHNMe2)SCH2Ph (from MeCOCH2SCH2Ph and Me2NCH(OMe)2 similarly affords 3(PhCH2S)-substituted products such as 29. Alkylation of the pyridinone anions produces mixtures of N- and O-substituted compounds, with the latter predominating; aminolysis of the isolated pyrones (R'NH2-HOAc, where R' = alkyl, Ar, HO, etc.) is the preferred route to the 1-R'-substituted pyridinones.
• Amide compounds and use of the same
  申请人：Takeda Pharmaceutical Company Limited

  公开号：US08329691B2

  公开（公告）日：2012-12-11

  A renin inhibitor comprising a compound represented by the formula: wherein each symbol is as defined in the description, or a salt thereof or a prodrug thereof. The compound of the present invention has a superior renin inhibitory activity, and thus is useful as an agent for the prophylaxis or treatment of hypertension, various organ damages attributable to hypertension and the like.

  一种肾素抑制剂，包括由下式表示的化合物：其中每个符号如描述中所定义，或其盐或前药。本发明的化合物具有优异的肾素抑制活性，因此可用作预防或治疗高血压、由高血压引起的各种器官损伤等的药剂。