(R)-1-(2-Hydroxy-phenyl)-2-o-tolyl-2,3-dihydro-1H-pyridin-4-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1-(2-Hydroxy-phenyl)-2-o-tolyl-2,3-dihydro-1H-pyridin-4-one
• 英文别名: (2R)-1-(2-hydroxyphenyl)-2-(2-methylphenyl)-2,3-dihydropyridin-4-one
• 化学式: C₁₈H₁₇NO₂
• 分子量: 279.338
• InChiKey: NXDQCIFDXWUDHT-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲基苯甲醛 、 alkaline earth salt of/the/ methylsulfuric acid 在 N-甲基咪唑 、 (R)-6,6'-dibromo-1,1'-binaphth-2-ol 、 zirconium(IV) tert-butoxide 作用下， 以 甲苯 为溶剂， 生成 (R)-1-(2-Hydroxy-phenyl)-2-o-tolyl-2,3-dihydro-1H-pyridin-4-one
  参考文献：
  名称：

  A Switch of Enantiofacial Selectivities Using Designed Similar Chiral Ligands in Zirconium-Catalyzed Asymmetric Aza Diels−Alder Reactions

  摘要：

  DOI：

  10.1021/jo9902300

文献信息

• The First Enantioselective Aza-Diels-Alder Reactions of Imino Dienophiles on Use of a Chiral Zirconium Catalyst
  作者：Shū Kobayashi、Susumu Komiyama、Haruro Ishitani

  DOI：10.1002/(sici)1521-3773(19980420)37:7<979::aid-anie979>3.0.co;2-5

  日期：1998.4.20

  Chiral dihydropyridone derivatives 3 are obtained in high yields and with good enantioselectivities by the title reaction of aldimines such as 1 with Danishefsky's diene 2. 6,6'-Dibromo-1,1'-binaphthol complexes with Group 4 metals serve as catalysts; zirconium proved to be especially effective.

  手性二氢吡啶酮衍生物3可通过醛亚胺（如1）与Danishefsky's diene 2的标题反应以高收率和良好的对映选择性得到。6,6'-Dibromo-1,1'-binaphthol配合物与第4组金属配合使用；锆被证明是特别有效的。
• Chiral Catalyst Optimization Using Both Solid-Phase and Liquid-Phase Methods in Asymmetric Aza Diels−Alder Reactions
  作者：Shū Kobayashi、Ken-ichi Kusakabe、Haruro Ishitani

  DOI：10.1021/ol005656b

  日期：2000.5.1

  In the presence of 1-5 mol % of a chiral zirconium catalyst, aza Diels-Alder reactions of aldimines with Danisheisky's dienes proceeded smoothly to afford the corresponding piperidine derivatives in high yields with high enantioselectivities. For the catalyst optimization, solid-phase and liquid-phase methods were successfully used. In the solid-phase approach, polymer-supported (R)-1,1'-binaphthols (BINOLs) have been synthesized and rapid optimization using the solid-phase reactions has been achieved. On the other hand, novel chiral zirconium cyanides were developed as excellent catalysts using the liquid-phase approach.