cyclocaric acid A

• 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: cyclocaric acid A
• 英文别名: (1R,2S,5S,10S,14R,15R,18R,21R,22R)-1,2,8,8,15,21-hexamethyl-19-oxahexacyclo[12.10.0.02,11.05,10.015,22.018,21]tetracos-11-ene-5-carboxylic acid
• 化学式: C₃₀H₄₆O₃
• 分子量: 454.693
• InChiKey: TYAXJAYEQFCSEV-ZBXZNUPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  常春藤皂苷元 在 四氢吡咯 、 四(三苯基膦)钯 、 L-Selectride 、 potassium carbonate 、 三苯基膦 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.2h， 生成 cyclocaric acid A
  参考文献：
  名称：

  Synthesis of Cyclocaric Acid A and Comparison to Material from Cyclocarya paliurus

  摘要：

  Components previously reported from Cyclocarya paliurus include the oleananes cyclocaric acids A and B, with cyclocaric acid A possessing an oxetane ring. Isolation of cyclocaric acid A from the plant extract and comparison to the literature report show that the compound originally reported as cyclocaric acid A is, in fact, hederagenin. This was confirmed by independent synthesis of the oxetane and indicates that cyclocaric acid A may not actually be a natural product.

  DOI：

  10.1021/np500575q

文献信息

• Synthesis of Cyclocaric Acid A and Comparison to Material from <i>Cyclocarya paliurus</i>
  作者：Matthew E. Wright、Jonathan Byrd、Chunnian He、Norma Dunlap

  DOI：10.1021/np500575q

  日期：2014.11.26

  Components previously reported from Cyclocarya paliurus include the oleananes cyclocaric acids A and B, with cyclocaric acid A possessing an oxetane ring. Isolation of cyclocaric acid A from the plant extract and comparison to the literature report show that the compound originally reported as cyclocaric acid A is, in fact, hederagenin. This was confirmed by independent synthesis of the oxetane and indicates that cyclocaric acid A may not actually be a natural product.