(4Z)-t-butyl 4-bromo-7-(2'-methyl-1',3'-dioxocyclopent-2'-yl)-3-oxohept-4-enoate | 448961-03-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (4Z)-t-butyl 4-bromo-7-(2'-methyl-1',3'-dioxocyclopent-2'-yl)-3-oxohept-4-enoate
• 英文别名: tert-butyl (Z)-4-bromo-7-(1-methyl-2,5-dioxocyclopentyl)-3-oxohept-4-enoate
• CAS: 448961-03-3
• 化学式: C₁₇H₂₃BrO₅
• 分子量: 387.271
• InChiKey: PEAUZLPEUNYFRA-WDZFZDKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (4Z)-t-butyl 4-bromo-7-(2'-methyl-1',3'-dioxocyclopent-2'-yl)-3-oxohept-4-enoate 在 samarium diiodide 、 caesium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.25h， 生成 rac-(5β,8α,9α,10β,13α,14α)-methyl 14-hydroxy-1,7,17-trioxoandrostane-10-carboxylate
  参考文献：
  名称：

  A Convergent Synthesis of the Cardenolide Skeleton:  Intramolecular Aldol Condensation via Reduction of α-Bromoketones

  摘要：

  Synthesis of the highly biologically valuable cardenolide backbone was achieved via anionic polycyclization. Bromoketone 18, obtained from double-Michael cycloaddition between cyclohexenone 14 and gamma,delta-unsaturated beta-ketoester 16, was efficiently aldolized under reductive conditions. The highly functionalized tetracyclic compound 52 is an important synthetic intermediate that is potentially amenable to natural cardenolide total synthesis.

  DOI：

  10.1021/jo025612b
• 作为产物：
  描述：

  3-(1-methyl-2,5-dioxocyclopentyl)propanal 在 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 26.0h， 生成 (4Z)-t-butyl 4-bromo-7-(2'-methyl-1',3'-dioxocyclopent-2'-yl)-3-oxohept-4-enoate
  参考文献：
  名称：

  A Convergent Synthesis of the Cardenolide Skeleton:  Intramolecular Aldol Condensation via Reduction of α-Bromoketones

  摘要：

  Synthesis of the highly biologically valuable cardenolide backbone was achieved via anionic polycyclization. Bromoketone 18, obtained from double-Michael cycloaddition between cyclohexenone 14 and gamma,delta-unsaturated beta-ketoester 16, was efficiently aldolized under reductive conditions. The highly functionalized tetracyclic compound 52 is an important synthetic intermediate that is potentially amenable to natural cardenolide total synthesis.

  DOI：

  10.1021/jo025612b

文献信息

• A Convergent Synthesis of the Cardenolide Skeleton:  Intramolecular Aldol Condensation via Reduction of α-Bromoketones
  作者：Daniel Chapdelaine、Julie Belzile、Pierre Deslongchamps

  DOI：10.1021/jo025612b

  日期：2002.8.1

  Synthesis of the highly biologically valuable cardenolide backbone was achieved via anionic polycyclization. Bromoketone 18, obtained from double-Michael cycloaddition between cyclohexenone 14 and gamma,delta-unsaturated beta-ketoester 16, was efficiently aldolized under reductive conditions. The highly functionalized tetracyclic compound 52 is an important synthetic intermediate that is potentially amenable to natural cardenolide total synthesis.