5,6-dimethoxy-2,2-dimethyl-2H-benzopyran | 67015-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5,6-dimethoxy-2,2-dimethyl-2H-benzopyran
• 英文别名: Ageratochromen；5,6-Dimethoxy-2,2-dimethylchromene
• CAS: 67015-34-3
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: GUTIIFGBTVZGPV-UHFFFAOYSA-N

物化性质

• 沸点：
  308.3±42.0 °C(Predicted)
• 密度：
  1.063±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-2,2-dimethyl-2H-benzopyran 、 2-(苄氧基)-5-氯苯甲醛 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以105 mg的产率得到9-Chloro-5-methoxy-2,2-dimethyl-3,4-dihydropyrano[2,3-b]xanthen-11-one
  参考文献：
  名称：

  Multidimensional optimization of promising antitumor xanthone derivatives

  摘要：

  A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI(50) of 5.1 mu M, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (K-p) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log K-p between 3 and 5 and the two membrane models showed a good correlation (r(2) = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.079
• 作为产物：
  描述：

  甲基雪松酮 在 萘-1,4-二腈 、 magnesium 作用下， 以 水 、 乙腈 为溶剂， 反应 2.67h， 生成 5,6-dimethoxy-2,2-dimethyl-2H-benzopyran
  参考文献：
  名称：

  Synthetic application of photoinduced single electron transfer reactions: a convenient synthetic approach for the 2,2-dimethyl-2H-chromene system

  摘要：

  DOI：

  10.1021/jo00245a047

文献信息

• PANDEY, G.;KRISHNA, A., J. ORG. CHEM., 53,(1988) N 10, 2364-2365
  作者：PANDEY, G.、KRISHNA, A.

  DOI：——

  日期：——
• Multidimensional optimization of promising antitumor xanthone derivatives
  作者：Carlos M.G. Azevedo、Carlos M.M. Afonso、Diana Sousa、Raquel T. Lima、M. Helena Vasconcelos、Madalena Pedro、João Barbosa、Arlene G. Corrêa、Salette Reis、Madalena M.M. Pinto

  DOI：10.1016/j.bmc.2013.03.079

  日期：2013.6

  A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI(50) of 5.1 mu M, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (K-p) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a log K-p between 3 and 5 and the two membrane models showed a good correlation (r(2) = 0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthetic application of photoinduced single electron transfer reactions: a convenient synthetic approach for the 2,2-dimethyl-2H-chromene system
  作者：G. Pandey、A. Krishna

  DOI：10.1021/jo00245a047

  日期：1988.5