2-(3-methylphenyl)-2,3-dihydro-4H-pyran-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-(3-methylphenyl)-2,3-dihydro-4H-pyran-4-one
• 英文别名: 2-(3-tolyl)-2,3-dihydro-4H-pyran-4-one；2-(3-Methylphenyl)-2,3-dihydropyran-4-one
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: WXLAYSQZJCFZHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (E)-1-Methoxy-5-m-tolyl-5-trimethylsilanyloxy-pent-1-en-3-one 在 三氟乙酸 作用下， 生成 2-(3-methylphenyl)-2,3-dihydro-4H-pyran-4-one
  参考文献：
  名称：

  Nafion-H-catalyzed Mukaiyama aldol condensations and hetero Diels–Alder reactions using aldehydes and imines. Part 15: General synthetic methods

  摘要：

  Nafion-H catalyzes the Mukaiyama aldol condensation between aromatic aldehydes and the Danishefsky diene whereas the corresponding imines directly undergo hetero Diels-Alder cyclization to form 2,3-dihydro-gamma -pyridones. Some chiral acetal derived aldehydes were round to undergo Mukaiyama aldol condensation in the presence of Lewis acids but not with Nafion-H. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01592-1

文献信息

• 3,3‘-Br₂-BINOL-Zn Complex:  A Highly Efficient Catalyst for the Enantioselective Hetero-Diels−Alder Reaction
  作者：Haifeng Du、Jiang Long、Jieyu Hu、Xin Li、Kuiling Ding

  DOI：10.1021/ol027034r

  日期：2002.11.1

  [reaction: see text] A BINOLate-zinc complex prepared in situ from Et(2)Zn and 3,3'-dibromo-1,1'-bi-2-naphthol (3,3'-Br(2)-BINOL) was found to be a highly efficient catalyst for the enantioselective hetero-Diels-Alder reaction of Danishefsky's diene and aldehydes to give 2-substituted 2,3-dihydro-4H-pyran-4-one in up to quantitative yield and 98% ee.

  [反应：参见正文]由Et（2）Zn和3,3'-dibromo-1,1'-bi-2-naththol（3,3'-Br（2）-BINOL原位制备的BINOLate-锌复合物）被发现是Danishefsky's二烯和醛对映选择性杂Diels-Alder反应的高效催化剂，可得到定量最高收率和98％ee的2-取代的2,3-二氢-4H-吡喃-4-酮。
• Discovery of Exceptionally Efficient Catalysts for Solvent-Free Enantioselective Hetero-Diels−Alder Reaction
  作者：Jiang Long、Jieyu Hu、Xiaoqiang Shen、Baoming Ji、Kuiling Ding

  DOI：10.1021/ja0172518

  日期：2002.1.1

  Combinatorial coordination chemistry strategy combined with high-throughput screening techniques has been successfully applied to engineering practical enantioselective catalysts for asymmetric hetero-Diels-Alder reaction. The reaction of Danishefsky's diene with a variety of aldehydes can be carried out with 0.1-0.005 mol % of H4-BINOL/Ti/H4-BINOL or H4-BINOL/Ti/H8-BINOL catalysts at room temperature under solvent- and MS-free conditions to afford dihydropyrone derivatives with up to quantitative yield and 99.8% ee.
• Dramatically Synergetic Effect of Carboxylic Acid Additive on Tridentate Titanium Catalyzed Enantioselective Hetero-Diels–Alder Reaction: Additive Acceleration and Nonlinear Effect
  作者：Yu Yuan、Jiang Long、Jie Sun、Kuiling Ding

  DOI：10.1002/1521-3765(20021104)8:21<5033::aid-chem5033>3.0.co;2-t

  日期：2002.11.4

  This paper describes the successful development of a group of highly, efficient chiral tridentate titanium catalysts for hetero-Diels - Alder reaction of Danishefsky's diene and a variety of aldehydes through ligand and additive diversity. Dramatically synergetic effect of carboxylic acid additives and influence of substituent in chiral Schiff base ligands on the enantioselectivities of the reaction are reported. It was found that a chiral drug Naproxen (A21) was a highly efficient additive for Ti-catalyzed HDA reaction, affording 2-substituted 2,3-dihydro-4H-pyran-4-one in up to 97% ee and > 99% yields. Quantitative study of the effect of chiral carboxylic acid A21 revealed that the reaction could be accelerated by one order of magnitude. Another interesting feature of present catalytic system is the existence of significant positive nonlinear effect. which indicates that the heterochiral Schiff base-titanium complexes may have higher stability than their homochiral counterparts. As a result. the homochiral Schiff base - titanium complexes with higher ee than that of starting ligand will react with carboxylic acid additive to form the more active species and predominate the catalytic process. The isolation and characterization of stable heterochiral ((+/-)-L1)(2)Ti complex has also been successful, which strongly supported the explanation for positive nonlinear effect observed in the catalytic system.
• Nafion-H-catalyzed Mukaiyama aldol condensations and hetero Diels–Alder reactions using aldehydes and imines. Part 15: General synthetic methods
  作者：R Kumareswaran、B.Gopal Reddy、Y.D Vankar

  DOI：10.1016/s0040-4039(01)01592-1

  日期：2001.10

  Nafion-H catalyzes the Mukaiyama aldol condensation between aromatic aldehydes and the Danishefsky diene whereas the corresponding imines directly undergo hetero Diels-Alder cyclization to form 2,3-dihydro-gamma -pyridones. Some chiral acetal derived aldehydes were round to undergo Mukaiyama aldol condensation in the presence of Lewis acids but not with Nafion-H. (C) 2001 Elsevier Science Ltd. All rights reserved.