2-Hydroxy-6-(4-methoxyphenyl)cyclohepta-2,4,6-trien-1-one | 16241-31-9

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 英文名称: 2-Hydroxy-6-(4-methoxyphenyl)cyclohepta-2,4,6-trien-1-one
• 英文别名: 2-hydroxy-6-(4-methoxyphenyl)cyclohepta-2,4,6-trien-1-one
• CAS: 16241-31-9
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: ONWOFQLLGGJDEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S,5R)-3-bromo-4-(4-methoxyphenyl)-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one 在 N,N-二甲基丙烯基脲 、 samarium diiodide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.34h， 以62%的产率得到2-Hydroxy-6-(4-methoxyphenyl)cyclohepta-2,4,6-trien-1-one
  参考文献：
  名称：

  呋喃酮转化为对苯二酚的途径：探讨β-thujaplicin类似物的抗增殖作用†

  摘要：

  距离天然托洛酮β-thujaplicin类似物的直接途径仅需四个步骤即可完成 呋喃。使用这种方法，合成并评估了一系列衍生物。这些化合物中的几种显示出对细菌和真菌病原体非常高的效力，并且对哺乳动物细胞具有良好的选择性。

  DOI：

  10.1039/c2ob26553b

文献信息

• The Tropylation of Polyhydric Phenols and the Dehydrogenation of Their Products
  作者：Kazuko Takahashi

  DOI：10.1246/bcsj.40.1462

  日期：1967.6

  polyhydric phenols, such as guaiacol, catechol, resorcinol, hydroquinone, 2, 6-dimethoxyphenol, pyrogallol and phloroglucinol, has been carried out. These polyhydric phenols were quite reactive with ethyl tropyl ether or with tropylium ion, and gave mono-, di-, or sometimes tri-tropyl derivatives. The dehydrogenation of tropylpolyhydric phenol methyl ethers gave stable aryltropilium ions. The methoxyphenyltropones

  已经进行了愈创木酚、儿茶酚、间苯二酚、对苯二酚、2,6-二甲氧基苯酚、连苯三酚和间苯三酚等多元酚的转酰化反应。这些多元酚与乙基托醚或托鎓离子具有很强的反应性，并产生单、二或有时三托基衍生物。tropylpolyhydric phenolmethyl ethers 的脱氢得到稳定的aryltropilium 离子。甲氧基苯基托酮和甲氧基苯基托酚酮也以良好的产率从 4-甲氧基苯基托鎓离子开始合成。
• Tropolones As Lead-Like Natural Products: The Development of Potent and Selective Histone Deacetylase Inhibitors
  作者：Sophia N. Ononye、Michael D. VanHeyst、E. Zachary Oblak、Wangda Zhou、Mohamed Ammar、Amy C. Anderson、Dennis L. Wright

  DOI：10.1021/ml400158k

  日期：2013.8.8

  Natural products have long been recognized as a rich source of potent therapeutics but further development is often limited by high structural complexity and high molecular weight. In contrast, at the core of the thujaplicins is a lead-like tropolone scaffold characterized by relatively low molecular weight, ample sites for diversification, and metal-binding functionality poised for targeting a range of metalloenzyme drug targets. Here, we describe the development of this underutilized scaffold for the discovery of tropolone derivatives that function as isozyme-selective inhibitors of the validated anticancer drug target, histone deacetylase (HDAC). Several monosubstituted tropolones display remarkable levels of selectivity for HDAC2 and potently inhibit the growth of T-cell lymphocyte cell lines. The tropolones represent a new chemotype of isozyme-selective HDAC inhibitors.
• The furan route to tropolones: probing the antiproliferative effects of β-thujaplicin analogs
  作者：E. Zachary Oblak、Erin S. D. Bolstad、Sophia N. Ononye、Nigel D. Priestley、M. Kyle Hadden、Dennis L. Wright

  DOI：10.1039/c2ob26553b

  日期：——

  A direct route to analogs of the naturally occurring tropolone β-thujaplicin has been developed in just four steps from furan. Using this method, a series of derivatives were synthesized and evaluated. Several of these compounds demonstrated very high levels of potency against bacterial and fungal pathogens with good selectivity over mammalian cells.

  距离天然托洛酮β-thujaplicin类似物的直接途径仅需四个步骤即可完成 呋喃。使用这种方法，合成并评估了一系列衍生物。这些化合物中的几种显示出对细菌和真菌病原体非常高的效力，并且对哺乳动物细胞具有良好的选择性。