10-cyclohexyl-7β,20β-dihydroxy-16α-methyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione | 14110-63-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯内酰胺
• 英文名称: 10-cyclohexyl-7β,20β-dihydroxy-16α-methyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione
• 英文别名: 10-cyclohexyl-7β,20β-dihydroxy-16α-methyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione；Dodecahydrophomin
• CAS: 14110-63-5
• 化学式: C₂₉H₄₉NO₅
• 分子量: 491.712
• InChiKey: QEXUUDRVYQHZBR-JPCRBDKGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  35.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  95.86
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  10-cyclohexyl-7β,20β-dihydroxy-16α-methyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione 在 吡啶 、 三氟化硼乙醚 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 7β-acetoxy-10-cyclohexyl-1,20β-dimethoxy-16α-methyl-(6αH)-24-oxa-[14]cytochalas-1-en-23-one
  参考文献：
  名称：

  [248。30-氧杂-（14）-细胞chalasanes的甲基化反应]。

  摘要：

  AbstractFor synthetic studies the protection of the hydroxyl groups of phomin (cytochalasin B) ((7S,22R,26R)‐7,26‐dihydroxy‐22‐methyl‐30‐oxa‐[14]cytochalasa‐6(18), 19t 27t‐trien‐1,29‐dion) (1), the dodecahydro‐derivative 2, and the dihydro‐derivative 4 by methylation was investigated. Treatment of 1 with CH3I/Ag2O gave the iminoether 6. The reaction of 4 with CH2N2/BF3 led to the di‐O‐methyl derivative 8 and to the N‐methyl‐di‐O‐methyl derivative 9, whereas 2 was transformed to the N‐methyl‐di‐O‐methyl compound 10 and to the iminoether 11.NaBH4 reduction of 3 yielded not only 4 but also the epimeric dihydro derivative 5.

  DOI：

  10.1002/hlca.19720550725
• 作为产物：
  描述：

  细胞松弛素B 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 生成 10-cyclohexyl-7β,20β-dihydroxy-16α-methyl-(6ξH)-24-oxa-[14]cytochalasane-1,23-dione
  参考文献：
  名称：

  Isolierung und Struktur der Antibiotica Phomin und 5-Dehydrophomin

  摘要：

  AbstractFrom cultures of a Phoma species (strain S 298) (Fungi imperfecti) two new antibiotics, phomine (1) and 5‐dehydrophomine (4) have been isolated. Phomine and 5‐dehydrophomine represent a novel type of macrolide antibiotics, the large lactone ring being fused to a highly substituted octahydro‐isoindole system. Both show cytostatic activity.

  DOI：

  10.1002/hlca.19700530404