(3β,5α,25R)-3-methoxyspirost-14-en-12-one | 304901-74-4

• 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,25R)-3-methoxyspirost-14-en-12-one
• CAS: 304901-74-4
• 化学式: C₂₈H₄₂O₄
• 分子量: 442.639
• InChiKey: LBQKTHXJCLOFKI-IXUMLHJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  32.0
• 可旋转键数：
  1.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (3β,5α,25R)-3-methoxyspirost-14-en-12-one 在 亚硝酸特丁酯 、 dimethyl sulfide borane 、 氧气 、 苯基锂 作用下， 以 四氢呋喃 、 乙醚 、 氯仿 、 环己烷 、 苯 为溶剂， 反应 12.0h， 生成 (3β,5α,12β,25R)-3-methoxy-17-(nitrooxy)spirost-14-ene-12-methanol
  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-12-keto-5α-spirostan-14-ene 在 氢氧化钾 、 2,6-二叔丁基吡啶 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (3β,5α,25R)-3-methoxyspirost-14-en-12-one
  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