5-benzyl-3,9-dimethylbenzo[de]chromene-7,8-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-benzyl-3,9-dimethylbenzo[de]chromene-7,8-dione
• 英文别名: 7-Benzyl-4,12-dimethyl-2-oxatricyclo[7.3.1.05,13]trideca-1(12),3,5(13),6,8-pentaene-10,11-dione
• 化学式: C₂₁H₁₆O₃
• 分子量: 316.356
• InChiKey: FSXDNIKZNPVHNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  维生素 K4 在 sodium hydroxide 、 tetrafluoroboric acid 、 potassium carbonate 、 sodium thiosulfate 、 叔丁胺 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 11.08h， 生成 5-benzyl-3,9-dimethylbenzo[de]chromene-7,8-dione
  参考文献：
  名称：

  Synthesis and Cytotoxicity of 9‐Substituted Benzo[de]chromene‐7,8‐dione and 5‐Benzyl‐9‐substituted Benzo[de]chromene‐7,8‐dione

  摘要：

  New Mansonone analogues of 9-substitued benzo[ de] chromene-7,8-dione 5b-e and 5-benzyl-9-substitued benzo[ de] chromene-7,8-dione 6a-e were prepared through a modified route. The first step involved a bulky base t-butylamine mediated regioselective deacetylation of 2-substituted-1,4-naphth-diyl diacetate, resulting in obtaining of monoacetate 4-acetate 2 in high yield. The mechanism of cyclization, debenzylation, and oxidation for the formation of 5a - e and 6a - e were discussed. The cytotoxicity of the prepared compounds 5 and 6 were comparable with naturally occurring Mansonone F.

  DOI：

  10.1080/00397910600764683

文献信息

• Synthesis and Cytotoxicity of 9‐Substituted Benzo[<i>de</i>]chromene‐7,8‐dione and 5‐Benzyl‐9‐substituted Benzo[<i>de</i>]chromene‐7,8‐dione
  作者：Shi‐Liang Huang、Yi Luo、Zhi‐Shu Huang、Xing‐Yuan Wang、Xian‐Zhang Bu、Pei‐Qing Liu、Lin Ma、Bing‐Fen Xie、Zong‐Chao Liu、Yue‐Ming Li、Albert S. C. Chan

  DOI：10.1080/00397910600764683

  日期：2006.9

  New Mansonone analogues of 9-substitued benzo[ de] chromene-7,8-dione 5b-e and 5-benzyl-9-substitued benzo[ de] chromene-7,8-dione 6a-e were prepared through a modified route. The first step involved a bulky base t-butylamine mediated regioselective deacetylation of 2-substituted-1,4-naphth-diyl diacetate, resulting in obtaining of monoacetate 4-acetate 2 in high yield. The mechanism of cyclization, debenzylation, and oxidation for the formation of 5a - e and 6a - e were discussed. The cytotoxicity of the prepared compounds 5 and 6 were comparable with naturally occurring Mansonone F.