methyl 3,3-dimethyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate | 1215491-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 3,3-dimethyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1215491-74-9
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: CTFJYFQXWWMHSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氧代-4-苯基-3-丁酸甲酯 、 异丁醛 在 4-二甲氨基吡啶 、 (1R,2R)-(-)-N-对甲苯磺酰基-1,2-环己二胺 、 pyridinium chlorochromate 作用下， 以 氯仿 、 二氯甲烷 为溶剂， 反应 48.0h， 以72%的产率得到methyl 3,3-dimethyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  The effect of hydrogen bond donors in asymmetric organocatalytic conjugate additions

  摘要：

  A series of primary amine organocatalysts with various hydrogen bond donors were prepared and examined in the conjugate addition of isobutyraldehyde and acetone to trans-beta-nitrostyrene and (E)-methyl 2-oxo-4-phenylbut-3-enoate. The effect of N-H acidity and hydrogen-bonding modes of the catalysts on the catalytic activity and enantioselectivity was studied. The experimental results did not support a general correlation of N-H acidity and hydrogen-bonding modes with catalytic activity and enantioselectivity. The catalysts with double hydrogen-bonding interactions provided better catalytic activities and enantioselectivities than the catalysts with single hydrogen-bonding interactions for the reaction of trans-beta-nitrostyrene. The catalyst with the most acidic N-H bond showed the best catalytic activity and enantioselectivity for the reaction of (E)-methyl 2-oxo-4-phenylbut-3-enoate. These results suggest that the effect of hydrogen bond donors in organocatalytic reactions may be highly dependent on the substrates and the reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.029