2-(3-Chloro-phenyl)-5-methyl-2,3-dihydro-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-Chloro-phenyl)-5-methyl-2,3-dihydro-pyran-4-one
• 英文别名: 2-(3-Chlorophenyl)-5-methyl-2,3-dihydropyran-4-one
• 化学式: C₁₂H₁₁ClO₂
• 分子量: 222.671
• InChiKey: AERJYAMDFPCCIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 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：

  (Z)-5-(3-Chloro-phenyl)-5-hydroxy-1-methoxy-2-methyl-pent-1-en-3-one 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 2-(3-Chloro-phenyl)-5-methyl-2,3-dihydro-pyran-4-one
  参考文献：
  名称：

  A convenient and versatile approach to 2,3-dihydro-4H-pyran-4-ones via tandem aldol reaction-conjugate addition

  摘要：

  Aldol reaction of enones 1a-c with aldehydes followed by intramolecular conjugate addition proceeded smoothly to afford corresponding 2 3-dihydro-4H-pyran-4-ones in high yields under mild conditions. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.010

文献信息

• Highly enantioselective hetero-Diels–Alder reaction between trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene and aldehydes catalyzed by (R)-BINOL–Ti(IV) complex
  作者：Bo Gao、Zhengyan Fu、Zhipeng Yu、Lan Yu、Yaozong Huang、Xiaoming Feng

  DOI：10.1016/j.tet.2005.04.016

  日期：2005.6

  An efficient enantioselective approach to 2,5-disubstituted dihydropyrones was developed. Some easily accessible inexpensive diol ligand metal complexes were employed, and [(R)-BINOL]2–Ti(OiPr)4 complex was found to be the most effective catalyst (up to 99% yield and 99% ee in the presence of 5 mol% catalyst) for the hetero-Diels–Alder reaction between trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1

  开发了一种对2,5-二取代的二氢吡喃酮的有效对映选择性方法。使用了一些容易获得的廉价二元醇配体金属配合物，发现[[ R ] -BINOL] 2 -Ti（O i Pr）4配合物是最有效的催化剂（在存在的情况下，收率高达99％，ee为99％ 5摩尔％催化剂）用于反式-1-甲氧基-2-甲基-3-三甲基甲硅烷氧基丁1,3-二烯（1）与醛之间的杂Diels-Alder反应。通过多种醛，包括芳族，杂芳族，α，β-不饱和和脂族醛，评估了该催化剂的潜力和通用性。根据苯甲醛反应中分离出的中间体通过1 H，13 C NMR和HRMS数据表明，该机理被认为是Mukaiyama羟醛途径。
• A convenient and versatile approach to 2,3-dihydro-4H-pyran-4-ones via tandem aldol reaction-conjugate addition
  作者：Bo Gao、Zhipeng Yu、Zhengyan Fu、Xiaoming Feng

  DOI：10.1016/j.tetlet.2006.01.010

  日期：2006.3

  Aldol reaction of enones 1a-c with aldehydes followed by intramolecular conjugate addition proceeded smoothly to afford corresponding 2 3-dihydro-4H-pyran-4-ones in high yields under mild conditions. (c) 2006 Elsevier Ltd. All rights reserved.