6-hydroxy-5-methoxy-2,2-dimethyl-2H-benzopyran | 1435265-81-8

• 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: 6-hydroxy-5-methoxy-2,2-dimethyl-2H-benzopyran
• 英文别名: 5-Methoxy-2,2-dimethylchromen-6-ol；5-methoxy-2,2-dimethylchromen-6-ol
• CAS: 1435265-81-8
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: GGSLMERKTYQSSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-hydroxy-5-methoxy-2,2-dimethyl-2H-benzopyran 在 正丁基锂 、 四甲基乙二胺 、 三氟甲磺酸三甲基硅酯 、 二乙胺 、 三乙胺 、 cesium fluoride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲基叔丁基醚 、 乙腈 为溶剂， 反应 68.58h， 生成
  参考文献：
  名称：

  Chromene / Chromane型芳烃前体的简捷合成及其应用

  摘要：

  报道了5,6-，6,7-和7,8-亚甲基/苯并二氢吡喃型芳烃前体的克级合成及其在向其他功能衍生物的区域选择性转化中的应用。Chromene / chromane型芳烃是在温和条件下产生的，可以进一步进行[2 + 2]，[3 + 2]和[4 + 2]环加成反应，亲核加成反应和σ插入反应，从而产生结构新颖的取代的色烯和苯并二氢吡喃。在三键邻位的含氧引导基团促进了反应的优异区域选择性，该基团可以被除去或切换成其他官能团，包括烯基，芳基，杂芳基和芳基氨基。

  DOI：

  10.1021/acs.joc.1c00493
• 作为产物：
  描述：

  5-羟基-2,2-二甲基-2H-色烯-6-甲醛 在 sodium hydrogensulfate monohydrate 、 双氧水 、 potassium carbonate 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 6-hydroxy-5-methoxy-2,2-dimethyl-2H-benzopyran
  参考文献：
  名称：

  Chromene / Chromane型芳烃前体的简捷合成及其应用

  摘要：

  报道了5,6-，6,7-和7,8-亚甲基/苯并二氢吡喃型芳烃前体的克级合成及其在向其他功能衍生物的区域选择性转化中的应用。Chromene / chromane型芳烃是在温和条件下产生的，可以进一步进行[2 + 2]，[3 + 2]和[4 + 2]环加成反应，亲核加成反应和σ插入反应，从而产生结构新颖的取代的色烯和苯并二氢吡喃。在三键邻位的含氧引导基团促进了反应的优异区域选择性，该基团可以被除去或切换成其他官能团，包括烯基，芳基，杂芳基和芳基氨基。

  DOI：

  10.1021/acs.joc.1c00493

文献信息

• Pyranoxanthones: Synthesis, growth inhibitory activity on human tumor cell lines and determination of their lipophilicity in two membrane models
  作者：Carlos M.G. Azevedo、Carlos M.M. Afonso、José X. Soares、Salette Reis、Diana Sousa、Raquel T. Lima、M. Helena Vasconcelos、Madalena Pedro、João Barbosa、Luís Gales、Madalena M.M. Pinto

  DOI：10.1016/j.ejmech.2013.09.012

  日期：2013.11

  The benzopyran and dihydrobenzopyran moieties can be considered as "privileged motifs" in drug discovery being good platforms for the search of new bioactive compounds. These moieties are commonly found fused to the xanthonic scaffold belonging to the biologically important family of the generally designated prenylated xanthones. Several pyranoxanthones have shown promising antitumor activity and since most of them are from natural origin, the biosynthetic pathway only allows a particular pattern of substitution which limits their structural diversity and renders any broad structure activity study hard to be established. Accordingly, with the aim of rationalizing the importance of the fused ring orientation and oxygenation pattern in pyranoxanthones, this study describes the synthesis of 14 new pyranoxanthones and evaluation of their cell growth inhibitory activity in four human tumor cell lines as well as their lipophilicity in two membrane models. This systematic approach allowed establishing structure activity and structure lipophilicity relationships for the obtained compounds in combination with 6 previously described compounds. From this work an angular pyranoxanthone scaffold emerged as particularly promising, presenting a potent cell growth inhibitory activity and suitable drug-like lipophilicity. (C) 2013 Elsevier Masson SAS. All rights reserved.
• 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.
• Concise Synthesis of Chromene/Chromane-Type Aryne Precursors and Their Applications
  作者：Yuan-Ze Xu、Jia-Wei Tian、Feng Sha、Qiong Li、Xin-Yan Wu

  DOI：10.1021/acs.joc.1c00493

  日期：2021.5.7

  The gram-scale synthesis of 5,6-, 6,7-, and 7,8-chromene/chromane-type aryne precursors and their applications in regioselective transformation to other functional derivatives is reported. Chromene/chromane-type arynes are generated under mild conditions, which can further undergo [2 + 2], [3 + 2], and [4 + 2] cycloaddition reactions, nucleophilic addition reactions, and σ-insertion reactions to produce

  报道了5,6-，6,7-和7,8-亚甲基/苯并二氢吡喃型芳烃前体的克级合成及其在向其他功能衍生物的区域选择性转化中的应用。Chromene / chromane型芳烃是在温和条件下产生的，可以进一步进行[2 + 2]，[3 + 2]和[4 + 2]环加成反应，亲核加成反应和σ插入反应，从而产生结构新颖的取代的色烯和苯并二氢吡喃。在三键邻位的含氧引导基团促进了反应的优异区域选择性，该基团可以被除去或切换成其他官能团，包括烯基，芳基，杂芳基和芳基氨基。