(3R,4R)-methyl 2-oxo-4-pentyl-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate | 1267588-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4R)-methyl 2-oxo-4-pentyl-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1267588-76-0
• 化学式: C₁₈H₂₂O₄
• 分子量: 302.37
• InChiKey: ICSXVKIKPTXMNG-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  苯乙酸 、 (E)-methyl 2-oxonon-3-enoate 在 三甲基乙酰氯 、 N,N-二异丙基乙胺 、 (2S,3R)-3,4-二氢-3-异丙基-2-苯基-2H-嘧啶并[2,1-b]苯并噻唑 作用下， 以 二氯甲烷 为溶剂， 反应 16.33h， 生成 (3R,4R)-methyl 2-oxo-4-pentyl-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate 、 methyl 2-oxo-4-pentyl-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
  参考文献：
  名称：

  Organocatalytic Functionalization of Carboxylic Acids: Isothiourea-Catalyzed Asymmetric Intra- and Intermolecular Michael Addition−Lactonizations

  摘要：

  Tetramisole promotes the catalytic asymmetric intramolecular Michael addition-lactonization of a variety of enone acids, giving carbo- and heterocyclic products with high diastereo- and enantiocontrol (up to 99:1 dr, up to 99% ee) that are readily derivatized to afford functionalized indene and dihydrobenzofuran carboxylates. Chiral isothioureas also promote the catalytic asymmetric intermolecular Michael addition-lactonization of arylacetic acids and alpha-keto-beta,gamma,-unsaturated esters, giving anti-dihydropyranones with high diastereo- and enantiocontrol (up to 98:2 dr, up to 99% ee).

  DOI：

  10.1021/ja109975c