N-phenyl-5-carbethoxy-4,6-dimethyl-1,2-dihydropyrid-2-one | 101293-88-3

• 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: N-phenyl-5-carbethoxy-4,6-dimethyl-1,2-dihydropyrid-2-one
• 英文别名: N-phenyl-5-carbethoxy-4,6-dimethylpyrid-2-one；2,4-dimethyl-6-oxo-1-phenyl-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester；2,4-dimethyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylic acid ethyl ester；4,6-Dimethyl-1-phenyl-5-ethoxycarbonyl-pyridon-(2)；4,6-Dimethyl-5-ethoxycarbonyl-1-phenyl-pyridon-(2)；Ethyl 2,4-dimethyl-6-oxo-1-phenyl-1,6-dihydropyridine-3-carboxylate；ethyl 2,4-dimethyl-6-oxo-1-phenylpyridine-3-carboxylate
• CAS: 101293-88-3
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: HHQHSWUNNJGPHS-UHFFFAOYSA-N

物化性质

• 熔点：
  92-93 °C
• 沸点：
  397.8±42.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-phenyl-5-carbethoxy-4,6-dimethyl-1,2-dihydropyrid-2-one 在 水 、 乙醚 、 title compound 作用下， 以 甲醇 、 sodium hydroxide 为溶剂， 反应 27.0h， 以to give 52.1 mg of colorless solid, yield 54%的产率得到4,6-Dimethyl-1-phenyl-5-carboxy-pyridon-(2)
  参考文献：
  名称：

  Pyridone derivatives as NK3 antagonists

  摘要：

  本发明涉及在治疗中有用的化合物，特别是在治疗精神病方面有用的化合物，以及包含该化合物的组合物和通过给予该化合物来治疗疾病的方法。

  公开号：

  US08207347B2
• 作为产物：
  描述：

  4,6-二甲基-2-氧-2H-吡喃-5-甲酸乙酯 、 苯胺 在 溶剂黄146 作用下， 反应 77.04h， 以33%的产率得到N-phenyl-5-carbethoxy-4,6-dimethyl-1,2-dihydropyrid-2-one
  参考文献：
  名称：

  [EN] PYRIDONE DERIVATIVES AS NK3 ANTAGONISTS
  [FR] DÉRIVÉS DE PYRIDONE ANTAGONISTES DE NK3

  摘要：

  本发明涉及一种具有式（I）的化合物，用于治疗，特别是在治疗精神病方面，包括所述化合物的组合物，以及通过给予该化合物来治疗疾病的方法。

  公开号：

  WO2011072691A1
• 作为试剂：
  描述：

  4,6-二甲基-2-氧-2H-吡喃-5-甲酸乙酯 、 苯胺 、 溶剂黄146 、 N-乙酰苯胺 、 4-乙酰胺苯乙酮 在 乙酸乙酯 、 正庚烷 、 N-phenyl-5-carbethoxy-4,6-dimethyl-1,2-dihydropyrid-2-one 作用下， 55.0 ℃ 、1.33 kPa 条件下， 反应 77.5h， 以906 mg of the title compound as pale yellow oil, yield 33% (non-pure additional fractions gave 886 mg of the title compound contaminated with acetanilide and 4′-acetamidoacetophenone)的产率得到N-phenyl-5-carbethoxy-4,6-dimethyl-1,2-dihydropyrid-2-one
  参考文献：
  名称：

  Pyridone derivatives as NK3 antagonists

  摘要：

  本发明涉及在治疗中有用的化合物，特别是在治疗精神病方面有用的化合物，以及包含该化合物的组合物和通过给予该化合物来治疗疾病的方法。

  公开号：

  US08207347B2

文献信息

• Chemical Hybridizing Agents for Chickpea (<i>Cicer arietinum</i> L.):  Leads from QSAR Analysis of Ethyl Oxanilates and Pyridones
  作者：Kajal Chakraborty、C. Devakumar

  DOI：10.1021/jf052435h

  日期：2006.3.1

  In the self-pollinated crops such as chickpea, induction of male sterility by deployment of chemical hybridizing agents (CHAs) facilitating "two-line" approach holds immense potential in heterosis breeding. A total of 40 test CHAs comprising 20 ethyl oxanilates and 20 pyridones were screened as potential CHAs on chickpea (variety BG 1088) at 500, 800, and 1000 ppm. Three test compounds mostly having either F (4)/Br (5)/CF3 (19) at the para position of the aryl ring from a pool of 20 ethyl oxanilates were identified as the most potent CHAs causing >= 99% induction of pollen sterility and > 90% total flower sterility at 1000-ppm test concentration. Among pyridone derivatives, N-(4-chlorophenyl)-5-carbethoxy-4,6-dimethyl, 1, 2-dihydropyrid-2-one (26) was found to be the most active. Quantitative structure activity relationship (QSAR) analysis has revealed a direct involvement of Swain-Lupton field constant, F, with the target bioactivity which implied that field rather than resonance effect (R) had a positive effect on the activity. The real guiding principle for selectivity was found out to be the hydrophobic parameter pi value. The QSAR models indicated that increased steric bulk at the 4-position on the phenyl ring is associated with enhanced activity. The CHAs appeared to act by mimicking UDP-glucose, the key substrate in the synthesis of callose, or lead to an imbalance in acid-base equilibrium in pollen mother cells resulting in dissolution of callose wall by premature callase secretion.
• Quantitative Structure−Activity Relationship Analysis as a Tool To Evaluate the Mode of Action of Chemical Hybridizing Agents for Wheat (<i>Triticum aestivum </i>L.)
  作者：Kajal Chakraborty、C. Devakumar

  DOI：10.1021/jf050187j

  日期：2005.5.1

  Augmentation of wheat production calls for introduction of wheat hybrids in cultivation. In the absence of viable alternative technology of hybrid wheat development, chemical induction of male sterility mediated technology based on chemical hybridizing agents (CHAs) holds a great potential. The QSAR method was applied to two families of CHAs in the N-acylanilines and pyridone class of chemistry. The models for each CHA family gave good correlation between the variations in log percent of male sterility and the steric-electrostatic properties of the sets. QSAR analysis has revealed a direct relationship of the Swain-Lupton constant F-p and molecular mass but an inverse relationship of MR, ES, and Swain-Lupton resonance constant R in influencing the bioactivity in the N-acylanilines. QSAR analysis of four parent families consisting of two training sets each of pyrid-2-ones and prid-4-ones revealed the positive contributions of field effect exemplified by the Swain-Lupton field constant (F) and the negative contributions of the molar refractivity (MR) of aromatic substituents in all but one training set. The QSAR models also indicated that increased steric bulk at the 4-position on the phenyl ring is associated with enhanced activity. These leads will be useful in explaining the CHA binding fit in the macromolecular receptor site.
• Chakraborty, Kajal; Devakumar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 3, p. 703 - 714
  作者：Chakraborty, Kajal、Devakumar

  DOI：——

  日期：——
• PYRIDONE DERIVATIVES AS NK3 ANTAGONISTS
  申请人：H. Lundbeck A/S

  公开号：EP2513061A1

  公开（公告）日：2012-10-24
• US8207347B2
  申请人：——

  公开号：US8207347B2

  公开（公告）日：2012-06-26