(1R,4R,5R,8R,11E,13R,14R,17R,18R,19R)-11-hydroxyimino-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-10-one | 2451-37-8

• 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: (1R,4R,5R,8R,11E,13R,14R,17R,18R,19R)-11-hydroxyimino-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-10-one
• CAS: 2451-37-8
• 化学式: C₃₀H₄₇NO₃
• 分子量: 469.708
• InChiKey: IHBJLYLXCRRMME-WOKNVCKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4R,5R,8R,11E,13R,14R,17R,18R,19R)-11-hydroxyimino-4,5,9,9,13,20,20-heptamethyl-24-oxahexacyclo[17.3.2.01,18.04,17.05,14.08,13]tetracosan-10-one 在 乙醇 、 溶剂黄146 、 potassium hydroxide 作用下， 反应 5.0h， 生成 (1R,4aR,6aR,6bR,8aR,13aR,13bR,15aR,15bR)-2,2,6a,6b,9,9,13a-heptamethyl-1,2,3,4,5,6,6a,6b,7,8,8a,9,10,13,13a,13b,14,15,15a,15b-icosahydro-1,4a-(epoxymethano)piceno[2,3-d][1,2,3]triazole
  参考文献：
  名称：

  Synthesis of Triterpene A-Condensed Azoles

  摘要：

  Lupane and 18 alpha H-oleanane alpha-hydroximino ketones were used to synthesize derivatives condensed at ring A with a substituted azole fragment, namely, C(2)-C(3)-fused oxazoles and 1,2,3-triazoles. Triterpene isoxazoles fused at the C(1)-C(2) bond are described for the first time. An optimized method was proposed for the synthesis of unsubstituted 1,2,3-triazoles, displaying cytotoxic activity (IC50 8.4-40.7 mu M) relative to rhabdomyosarcoma, lung carcinoma, and MS melanoma cell lines.

  DOI：

  10.1007/s10593-014-1449-8