(2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate | 448961-11-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate
• 英文别名: [(1R,2S,3R,4S)-3-[N-(benzenesulfonyl)-3,5-dimethylanilino]-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (1R,2S)-2-(furan-3-yl)-5-oxocyclopentane-1-carboxylate
• CAS: 448961-11-3
• 化学式: C₃₄H₃₉NO₆S
• 分子量: 589.753
• InChiKey: HKNUJJDAKIIERA-JTWHRLRWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  42
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-carboxylate 在 potassium tert-butylate 、 potassium hydride 、 二异丁基氢化铝 、 lithium iodide 作用下， 以 四氢呋喃 、 2,4,6-三甲基吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 12.17h， 生成 (1'R/S,2'R,3'S)-3-[3'-(3-furyl)-1'-hydroxy-2'-methyl-cyclopent-2'-yl]-propanol
  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 、 双氧水 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.25h， 生成 (2R,3S,1'R,2'S,3'R)-3-[N-benzenesulfonyl-N-(3,5-dimethylphenyl)-amino]-bornan-2'-yl 3-(3-furyl)-cyclopentan-1-one-2-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

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.