methyl 7-(4-chlorophenyl)-2,3,7-trioxoheptanoate | 1384176-88-8

• 英文名称: methyl 7-(4-chlorophenyl)-2,3,7-trioxoheptanoate
• CAS: 1384176-88-8
• 化学式: C₁₄H₁₃ClO₅
• 分子量: 296.707
• InChiKey: CLKMQEFCQBVIDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 7-(4-chlorophenyl)-2,3,7-trioxoheptanoate 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以69%的产率得到methyl anti-2-(4-chlorobenzoyl)-1-hydroxy-5-oxocyclopentane-1-carboxylate
  参考文献：
  名称：

  Divergent Stereocontrol of Acid Catalyzed Intramolecular Aldol Reactions of 2,3,7-Triketoesters: Synthesis of Highly Functionalized Cyclopentanones

  摘要：

  The intramolecular acid catalyzed aldol cyclization of 2,3,7-triketoesters formed from zeta-keto-alpha-diazo-beta-ketoesters provides highly functionalized cyclopentanones with good diastereoselectivity in high overall yields via kinetically controlled and stereodivergent catalytic processes. Lewis acid catalysis gives high selectivity for the 1,2-anti tetrasubstituted cyclopentanones, whereas Bronsted acid catalysis produces the corresponding 1,2-syn diastereomer.

  DOI：

  10.1021/ol301317a
• 作为产物：
  描述：

  methyl 7-(4-chlorophenyl)-2,2-dihydroxy-3,7-dioxoheptanoate 100.0 ℃ 、1.33 kPa 条件下， 反应 2.0h， 生成 methyl 7-(4-chlorophenyl)-2,3,7-trioxoheptanoate
  参考文献：
  名称：

  Divergent Stereocontrol of Acid Catalyzed Intramolecular Aldol Reactions of 2,3,7-Triketoesters: Synthesis of Highly Functionalized Cyclopentanones

  摘要：

  The intramolecular acid catalyzed aldol cyclization of 2,3,7-triketoesters formed from zeta-keto-alpha-diazo-beta-ketoesters provides highly functionalized cyclopentanones with good diastereoselectivity in high overall yields via kinetically controlled and stereodivergent catalytic processes. Lewis acid catalysis gives high selectivity for the 1,2-anti tetrasubstituted cyclopentanones, whereas Bronsted acid catalysis produces the corresponding 1,2-syn diastereomer.

  DOI：

  10.1021/ol301317a