(3R,4R)-ethyl 4-(4-nitrophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate | 1267588-62-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3R,4R)-ethyl 4-(4-nitrophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate
• CAS: 1267588-62-4
• 化学式: C₂₀H₁₇NO₆
• 分子量: 367.358
• InChiKey: QFJHHCZSTXNHSP-WMZOPIPTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  95.74
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  potassium (E)-4-(4-nitrophenyl)-2-oxobut-3-enoate 在 三甲基乙酰氯 、 N,N-二异丙基乙胺 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 16.33h， 生成 (3R,4R)-ethyl 4-(4-nitrophenyl)-2-oxo-3-phenyl-3,4-dihydro-2H-pyran-6-carboxylate 、 (3R,4R)-ethyl 4-(4-nitrophenyl)-2-oxo-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