4-oxo-2-phenyl-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-oxo-2-phenyl-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl 4-oxo-2-phenyl-3,4-dihydro-2H-pyran-2-carboxylate；methyl 4-oxo-2-phenyl-3H-pyran-2-carboxylate
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: IAVKKQAOMYSPMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酰甲酸甲酯 、 反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 在 ytterbium tris<(R)-(-)-1,1'-binaphthyl-2,2'-diyl phosphate> 作用下， 以 二氯甲烷 为溶剂， 反应 11.0h， 以99%的产率得到4-oxo-2-phenyl-3,4-dihydro-2H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Chiral rare earth organophosphates as homogeneous Lewis acid catalysts for the highly enantioselective hetero-Diels–Alder reactions

  摘要：

  Various trivalent rare earth-chiral phosphate complexes [(R)-l-RE, (R)-3-RE, and (R)-4-Ce] were prepared and evaluated as a Lewis acid catalyst for the asymmetric hetero-Diels-Alder reaction of aldehydes with the Danishefsky's diene. Some of them effectively promoted the reaction at room temperature in the presence or absence of achiral additives under homogeneous conditions to afford the corresponding cycloadducts with high ee's (up to 99% ee). During these reactions, remarkably high asymmetric amplifications (positive nonlinear effects) were observed as the first example in the metal ion-chiral ligand 1:3 catalytic system. A scandium catalyst bearing the H-8-BNP ligand, (R)-3-Sc, could be recovered after the reaction and successfully reused for the next round of reactions. In addition, the hetero-Diels-Alder reaction of alpha-keto esters was effectively catalyzed by the ytterbium complex, (R)-l-Yb, without any additives thus producing the asymmetric quaternary carbon in excellent enantioselectivities (up to > 99% ee). (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.06.011

文献信息

• DABCO-Mediated [4+2] Annulation of But-3-yn-2-one and Activated Ketones: Facile Preparation of 2,3-Dihydropyran-4-one
  作者：Zhong Lian、Qian-Yi Zhao、Yin Wei、Min Shi

  DOI：10.1002/ejoc.201200264

  日期：2012.6

  that nitrogen-containing Lewis base mediated [4+2] annulation of but-3-yn-2-one with activated ketones could proceed efficiently to give the corresponding 2,3-dihydropyran-4-ones in moderate to good yields under mild conditions. The substrate scope has been carefully examined. Moreover, a plausible reaction mechanism for the [4+2] annulation of but-3-yn-2-one with activated ketones mediated by DABCO has

  我们发现含氮路易斯碱介导的 but-3-yn-2-one 与活化酮的 [4+2] 环化可以有效地进行，以中等至良好的产率得到相应的 2,3-dihydropyran-4-ones。条件温和。底物范围已经过仔细检查。此外，基于先前的文献和我们自己的研究，已经提出了一种由 DABCO 介导的but-3-yn-2-one 与活化酮的 [4+2] 环化的合理反应机制。
• Efficient Organocatalytic Hetero-Diels-Alder Reactions of Activated Ketones under High Pressure for Direct Access to δ-Lactones¹
  作者：Hiyoshizo Kotsuki、Kaori Mori、Jacques Maddaluno、Keiji Nakano、Yoshiyasu Ichikawa

  DOI：10.1055/s-0029-1217718

  日期：2009.9

  A general and efficient protocol for the high-pressure-promoted hetero-Diels-Alder reactions of activated ketones has been developed. The reactions are successfully achieved by thiourea-derived organocatalysts, and the desired adducts, convenient precursors of δ-lactones, are obtained in good to high yields.

  已经开发了一种用于活化酮的高压促进的异-Diels-Alder 反应的通用和有效的协议。该反应通过硫脲衍生的有机催化剂成功实现，并以良好到高产率获得所需的加合物，即 δ-内酯的方便前体。
• Chiral rare earth organophosphates as homogeneous Lewis acid catalysts for the highly enantioselective hetero-Diels–Alder reactions
  作者：Hiroshi Furuno、Tetsuji Hayano、Takeshi Kambara、Yuichi Sugimoto、Takeshi Hanamoto、Yumiko Tanaka、Yong Zhi Jin、Takumi Kagawa、Junji Inanaga

  DOI：10.1016/j.tet.2003.06.011

  日期：2003.12

  Various trivalent rare earth-chiral phosphate complexes [(R)-l-RE, (R)-3-RE, and (R)-4-Ce] were prepared and evaluated as a Lewis acid catalyst for the asymmetric hetero-Diels-Alder reaction of aldehydes with the Danishefsky's diene. Some of them effectively promoted the reaction at room temperature in the presence or absence of achiral additives under homogeneous conditions to afford the corresponding cycloadducts with high ee's (up to 99% ee). During these reactions, remarkably high asymmetric amplifications (positive nonlinear effects) were observed as the first example in the metal ion-chiral ligand 1:3 catalytic system. A scandium catalyst bearing the H-8-BNP ligand, (R)-3-Sc, could be recovered after the reaction and successfully reused for the next round of reactions. In addition, the hetero-Diels-Alder reaction of alpha-keto esters was effectively catalyzed by the ytterbium complex, (R)-l-Yb, without any additives thus producing the asymmetric quaternary carbon in excellent enantioselectivities (up to > 99% ee). (C) 2003 Elsevier Ltd. All rights reserved.
• Hetero Diels-Alder Type Reactions Between Danishefsky’s Dienes in the Presence of Lewis Base Catalysts. An Efficient Method for the Synthesis of Substituted 2,3-Dihydropyran-4-ones
  作者：Teruaki Mukaiyama、Takayuki Kitazawa

  DOI：10.3987/com-06-s(o)52

  日期：——