(2Z,2'R,3'R)-methyl 2-bromo-5-[3'-(3-furyl)-2'-methyl-1'-oxocyclopent-2'-yl]-pent-2-enoate | 448961-19-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2Z,2'R,3'R)-methyl 2-bromo-5-[3'-(3-furyl)-2'-methyl-1'-oxocyclopent-2'-yl]-pent-2-enoate
• 英文别名: methyl (Z)-2-bromo-5-[(1R,2R)-2-(furan-3-yl)-1-methyl-5-oxocyclopentyl]pent-2-enoate
• CAS: 448961-19-1
• 化学式: C₁₆H₁₉BrO₄
• 分子量: 355.228
• InChiKey: TXFUILQJQMSZNF-HMQHSOQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2Z,2'R,3'R)-methyl 2-bromo-5-[3'-(3-furyl)-2'-methyl-1'-oxocyclopent-2'-yl]-pent-2-enoate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以74%的产率得到(2Z,1'R/1'S,2'R,3'S)-2-bromo-5-[3'-(3-furyl)-1'-hydroxy-2'-methylcyclopent-2'-yl]-pent-2-enol
  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：

  2-甲氧羰基环戊酮 在 吡啶 、 4-二甲氨基吡啶 、 正丁基锂 、 草酰氯 、 potassium tert-butylate 、 双氧水 、 potassium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 、 lithium iodide 作用下， 以 四氢呋喃 、 2,4,6-三甲基吡啶 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 17.0h， 生成 (2Z,2'R,3'R)-methyl 2-bromo-5-[3'-(3-furyl)-2'-methyl-1'-oxocyclopent-2'-yl]-pent-2-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.