3,6,9-trimethyl-naphtho[1,8-bc]pyran-7,8-dione | 24615-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3,6,9-trimethyl-naphtho[1,8-bc]pyran-7,8-dione
• 英文别名: 3,9-dimethylbenzo[de]chromene-7,8-dione；mansonone F；3,9-dimethyl-benzo[de]chromene-7,8-dione；3,9-Dimethyl-1-oxa-phenalenchinon-(7,8)；4,12-Dimethyl-2-oxatricyclo[7.3.1.05,13]trideca-1(12),3,5(13),6,8-pentaene-10,11-dione
• CAS: 24615-06-3
• 化学式: C₁₄H₁₀O₃
• 分子量: 226.232
• InChiKey: YREHARQHCMLSJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• 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

• 作为反应物：
  描述：

  3,6,9-trimethyl-naphtho[1,8-bc]pyran-7,8-dione 、 邻苯二胺 以 溶剂黄146 为溶剂， 生成 4,7-dimethyl-isochromeno[8,1-ab]phenazine
  参考文献：
  名称：

  Biflorine发色体系合成1-oxa-phenalen衍生物

  摘要：

  为了通过比较吸收光谱来支持双弗洛林的结构式I，已经合成了1-氧杂苯二烯（II）和1-氧杂苯二烯-7,8-醌的几种衍生物。

  DOI：

  10.1002/hlca.19630460142
• 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 3,6,9-trimethyl-naphtho[1,8-bc]pyran-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

• The structure–activity relationships of mansonone F, a potent anti-MRSA sesquiterpenoid quinone: SAR studies on the C6 and C9 analogs
  作者：Young-Ger Suh、Sun Nam Kim、Dong-Yun Shin、Soon-Sil Hyun、Do-Sang Lee、Kyung-Hoon Min、Sae Mi Han、Funan Li、Eung-Chil Choi、Seong-Hak Choi

  DOI：10.1016/j.bmcl.2005.09.024

  日期：2006.1

  For the systematic SAR study on mansonone F, a series of C6 and C9 analogs of mansonone F have been synthesized and their anti-MRSA activities were evaluated. Most of the analogs exhibited good or excellent anti-MRSA activities. In particular, the 6-n-butylmansonone F showed fourfold higher antibacterial activities compared to that of vancomycin. (c) 2005 Published by Elsevier Ltd.
• 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.
• Synthese eines 1-Oxa-phenalen-Derivates mit dem chromophoren System des Biflorins
  作者：Heather N. Grant、V. Prelog、R. P. A. Sneeden

  DOI：10.1002/hlca.19630460142

  日期：——

  Several derivatives of 1-oxaphenalene (II) and 1-oxaphenalene-7,8-quinone have been synthesized in order to support the constitution I of biflorin by comparison of the absorption spectra.

  为了通过比较吸收光谱来支持双弗洛林的结构式I，已经合成了1-氧杂苯二烯（II）和1-氧杂苯二烯-7,8-醌的几种衍生物。