alkannane leucoacetate | 42991-36-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: alkannane leucoacetate
• 英文别名: [4,5,8-Triacetyloxy-6-(4-methylpent-3-enyl)naphthalen-1-yl] acetate
• CAS: 42991-36-6
• 化学式: C₂₄H₂₆O₈
• 分子量: 442.466
• InChiKey: NJGMDSXWOCVAID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  去氧紫草素 、 乙酸酐 在 sodium acetate 、 锌 作用下， 生成 alkannane leucoacetate
  参考文献：
  名称：

  Shukla,Y.N. et al., Indian Journal of Chemistry, 1973, vol. 11, p. 528 - 529

  摘要：

  DOI：

文献信息

• Antitumor activity of shikonin, alkannin and their derivatives. II. X-ray analysis of cyclo-alkannin leucoacetate, tautomerism of alkannin and cyclo-alkannin and antitumor activity of alkannin derivatives.
  作者：USHIO SANKAWA、HIDEAKI OTSUKA、YOSHITOMO KATAOKA、YOICHI IITAKA、AKIO HOSHI、KAZUO KURETANI

  DOI：10.1248/cpb.29.116

  日期：——

  Cyclo-alkannin and cycloshikonin were formerly considered to be derivatives of hydroanthraquinone 3. However, chemical and spectral investigation revealed that cycloalkannin possesses no secondary hydroxyl group. Thus, the structure of cyclo-alkannin leucoacetate (8) was determined by X-ray analysis, by the direct method ; the final R index with hydrogen atoms except for those of methyl groups was 0.065. The cyclization of alkannin and shikonin is a reaction between the hydroxyl group and double bond and does not involve the formation of a carbocyclic ring. In 1H-NMR both alkannin and cyclo-alkannin show two singlet signals arising from the protons of the aromatic and quinonic rings. The absence of coupling and lower chemical shift values suggests delocalization of the quinonic ring so that these compounds can be regarded as consisting of tautomeric structures (10, 11). The results of antitumor tests on alkannin and cycloalkannin derivatives (6, 7, 8, 10, 11) are also reported.

  环状阿尔坎宁和环状紫草素以前被认为是氢化蒽醌的衍生物3。然而，化学和光谱研究显示，环状阿尔坎宁不含次级羟基。因此，通过直接法X射线分析确定了环状阿尔坎宁亮氨酸乙酸盐（8）的结构；氢原子（甲基除外）的最终R指数为0.065。阿尔坎宁和紫草素的环化是羟基和双键之间的反应，不涉及碳环的形成。在1H-NMR中，阿尔坎宁和环状阿尔坎宁都显示出由芳香环和醌环的质子产生的两个单线信号。由于没有偶联和较低的化学位移值，表明醌环的离域性，因此这些化合物可以被视为由互变异构体结构组成（10、11）。还报告了阿尔坎宁和环状阿尔坎宁衍生物（6、7、8、10、11）的抗肿瘤测试结果。
• Shukla,Y.N. et al., Indian Journal of Chemistry, 1973, vol. 11, p. 528 - 529
  作者：Shukla,Y.N. et al.

  DOI：——

  日期：——