(3β,5α,12β,20ξ,25ξ)-3-(acetyloxy)-12,26-dihydroxycholesta-14,16-dien-22-one inner spirobicyclic acetal | 304902-01-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (3β,5α,12β,20ξ,25ξ)-3-(acetyloxy)-12,26-dihydroxycholesta-14,16-dien-22-one inner spirobicyclic acetal
• CAS: 304902-01-0
• 化学式: C₂₉H₄₂O₄
• 分子量: 454.65
• InChiKey: QJZSEFAVLNHZCW-DFNGSGKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  马来酰亚胺 、 (3β,5α,12β,20ξ,25ξ)-3-(acetyloxy)-12,26-dihydroxycholesta-14,16-dien-22-one inner spirobicyclic acetal 以 二氯甲烷 为溶剂， 反应 72.0h， 以64%的产率得到(3β,5α,12β,15β,16β,20ξ,25ξ)-3-(acetyloxy)-15,16-dihydro-12,26-dihydroxy-14,17-etheno-1'H-cholest-15-eno-[15,16c]pyrrole-2',5',22-trione inner spirocyclic acetal
  参考文献：
  名称：

  Synthesis of Cytostatic Tetradecacyclic Pyrazines and a Novel Reduction-Oxidation Sequence for Spiroketal Opening in Sapogenins

  摘要：

  Aiming towards spiroketal-modified artificial cephalostatin molecules, two orthogonal approaches were investigated. First, the introduction of 17-O-functionality into hecogenin derivatives with a closed spiroketal moiety was accomplished by different remote-oxidation procedures. These allowed the synthesis of tetradecacyclic artificial cephalostatin molecules with improved tumor-inhibiting properties. Second, a novel reduction-oxidation pathway for spiroketal opening in sapogenins was discovered, which should provide the basis for a broad access towards spiroketal-modified building blocks for cephalostatins.

  DOI：

  10.1002/1522-2675(20000809)83:8<1854::aid-hlca1854>3.0.co;2-4
• 作为产物：
  描述：

  3β-acetoxy-12α-hydroxy-5α-spirostan-14-ene 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以40%的产率得到(3β,5α,12β,20ξ,25ξ)-3-(acetyloxy)-12,26-dihydroxycholesta-14,16-dien-22-one inner spirobicyclic acetal
  参考文献：
  名称：

  Synthesis of Cytostatic Tetradecacyclic Pyrazines and a Novel Reduction-Oxidation Sequence for Spiroketal Opening in Sapogenins

  摘要：

  Aiming towards spiroketal-modified artificial cephalostatin molecules, two orthogonal approaches were investigated. First, the introduction of 17-O-functionality into hecogenin derivatives with a closed spiroketal moiety was accomplished by different remote-oxidation procedures. These allowed the synthesis of tetradecacyclic artificial cephalostatin molecules with improved tumor-inhibiting properties. Second, a novel reduction-oxidation pathway for spiroketal opening in sapogenins was discovered, which should provide the basis for a broad access towards spiroketal-modified building blocks for cephalostatins.

  DOI：

  10.1002/1522-2675(20000809)83:8<1854::aid-hlca1854>3.0.co;2-4