(3''β,5''α,12''β,25''R)-3''-methoxydispiro[cyclohexa-2,5-diene-1,2'-[1,3]dioxolane-4',12''-spirost[14]en]-4-one | 304901-90-4

• 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: (3''β,5''α,12''β,25''R)-3''-methoxydispiro[cyclohexa-2,5-diene-1,2'-[1,3]dioxolane-4',12''-spirost[14]en]-4-one
• CAS: 304901-90-4
• 化学式: C₃₅H₄₈O₆
• 分子量: 564.763
• InChiKey: VILSWZFWNHVMTA-OBDVBMNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  41
• 可旋转键数：
  1
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3''β,5''α,12''β,25''R)-3''-methoxydispiro[cyclohexa-2,5-diene-1,2'-[1,3]dioxolane-4',12''-spirost[14]en]-4-one 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 96.0h， 以48%的产率得到(3β,5α,12β,25R)-12-[(2-chloro-4-hydroxyphenoxy)methyl]-3-methoxyspirost-4-en-12-ol
  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,5α,25R)-3-hydroxyspirost-14-en-12-one 在 2,6-二叔丁基吡啶 、 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 6.17h， 生成 (3''β,5''α,12''β,25''R)-3''-methoxydispiro[cyclohexa-2,5-diene-1,2'-[1,3]dioxolane-4',12''-spirost[14]en]-4-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

文献信息

• Synthesis of Cytostatic Tetradecacyclic Pyrazines and a Novel Reduction-Oxidation Sequence for Spiroketal Opening in Sapogenins
  作者：Siegfried Bäsler、Annette Brunck、Rolf Jautelat、Ekkehard Winterfeldt

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

  日期：2000.8.9

  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.