(R)-1-(2-hydroxyphenyl)-2-(naphthalen-1-yl)-2,3-dihydropyridin-4(1H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-1-(2-hydroxyphenyl)-2-(naphthalen-1-yl)-2,3-dihydropyridin-4(1H)-one
• 英文别名: (2R)-1-(2-hydroxyphenyl)-2-naphthalen-1-yl-2,3-dihydropyridin-4-one
• 化学式: C₂₁H₁₇NO₂
• 分子量: 315.371
• InChiKey: SLGRQVVASFHIJO-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  1-tert-butoxy-3-trimethylsilyloxy butadiene 、 N-1-naphthyl-2-hydroxyaniline 在 N-甲基咪唑 、 C₃₀H₂₆O₃ 、 niobium(V) methoxide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 48.0h， 以89%的产率得到(R)-1-(2-hydroxyphenyl)-2-(naphthalen-1-yl)-2,3-dihydropyridin-4(1H)-one
  参考文献：
  名称：

  铌催化的高对映选择性氮杂-Diels-Alder反应

  摘要：

  铌基手性路易斯酸被发现是亚胺与Danishefsky二烯的氮杂Diels-Alder反应的高效催化剂。对于芳族和脂族亚胺，反应以高对映选择性和高收率进行。所开发的方法应用于（+）-天麻碱的全合成。

  DOI：

  10.1002/adsc.200700615

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。
• A Switch of Enantiofacial Selectivities Using Designed Similar Chiral Ligands in Zirconium-Catalyzed Asymmetric Aza Diels−Alder Reactions
  作者：Shū Kobayashi、Ken-ichi Kusakabe、Susumu Komiyama、Haruro Ishitani

  DOI：10.1021/jo9902300

  日期：1999.6.1
• 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.
• Niobium-Catalyzed Highly Enantioselective Aza-Diels–Alder Reactions
  作者：Václav Jurčík、Kenzo Arai、Matthew M. Salter、Yasuhiro Yamashita、Shū Kobayashi

  DOI：10.1002/adsc.200700615

  日期：2008.3.25

  Niobium-based chiral Lewis acid was found to be highly effective catalyst for aza-Diels–Alder reactions of imines with Danishefsky‘s dienes. The reactions proceed in high yield with high enantioselectivity for both aromatic and aliphatic imines. The developed methodology was applied to total synthesis of (+)-anabasine.

  铌基手性路易斯酸被发现是亚胺与Danishefsky二烯的氮杂Diels-Alder反应的高效催化剂。对于芳族和脂族亚胺，反应以高对映选择性和高收率进行。所开发的方法应用于（+）-天麻碱的全合成。