4-Phenyl-tropolon | 56968-75-3

• 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: 4-Phenyl-tropolon
• 英文别名: 2-hydroxy-6-phenylcyclohepta-2,4,6-trien-1-one
• CAS: 56968-75-3
• 化学式: C₁₃H₁₀O₂
• 分子量: 198.221
• InChiKey: MAAPIYPCXMEMAV-UHFFFAOYSA-N

物化性质

• 熔点：
  95 °C
• 沸点：
  395.1±42.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-Phenyl-tropolon 在 乙醇 、 铂 作用下， 生成 4-phenyl-cycloheptane-1,2-diol
  参考文献：
  名称：

  Synthesis of Substituted Tropolones

  摘要：

  DOI：

  10.1021/ja01098a014
• 作为产物：
  描述：

  2-chloro-3-phenyltropolone 在 氢氧化钾 、 乙醇 作用下， 生成 4-Phenyl-tropolon
  参考文献：
  名称：

  Reaction of 2-Chloro-3-phenyltropone and 2-Chloro-7-phenyltropone with Ammonia and Amines

  摘要：

  DOI：

  10.1246/bcsj.32.272

文献信息

• 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。
• The palladium-mediated cross-coupling of bromotropolones with organostannanes; application to concise syntheses of β-dolabrin, β-thujaplicin, 7-methoxy-4-isopropyltropolone, and β-thujaplicinol
  作者：Martin G. Banwell、Maree P. Collis、Geoffrey T. Crisp、John N. Lambert、Monica E. Reum、Judith A. Scoble

  DOI：10.1039/c39890000616

  日期：——

  The bromotropolones (1), (2), and (3) cross-couple with organostannanes in the presence of palladium(0) to produce alkyl, alkenyl, or aryl substituted tropolones; the methodology has been applied to the synthesis of the monoterpenes β-dolabrin (4), β-thujaplicin (5), 7-methoxy-4-isopropyltropolone (7), and β-thujaplicinol (8).

  在钯（0）的存在下，溴对苯二酮（1），（2）和（3）与有机锡烷交联以产生烷基，烯基或芳基取代的对苯二酚；该方法已被应用于合成单萜β-杜拉布林（4），β-thujaplicin（5），7-甲氧基-4-异丙基Tropolone （7）和β-thujaplicinol（8）。
• Stereo- and regiocontrolled hydroxylation of oxyallyl [4+3] cycloadducts. A concise synthesis of hinokitiol
  作者：Jae Chol Lee、Sung Yun Cho、Jin Kun Cha

  DOI：10.1016/s0040-4039(99)01589-0

  日期：1999.10

  Stereo- and regioselective hydroxylation of 8-oxabicyclo[3.2.1]oct-6-en-3-ones was achieved by the action of (diacetoxyiodo)benzene in methanolic potassium hydroxide (the Moriarty oxidation). Subsequent double elimination afforded a convenient preparation of substituted tropolones, as exemplified in a three-step synthesis of hinokitiol (1).

  通过（二乙酰氧基碘）苯在甲醇氢氧化钾中的作用（Moriarty氧化）实现了8-氧杂双环[3.2.1] oct-6-en-3-ones的立体和区域选择性羟基化。随后的双重消除提供了取代的对苯二酚的方便制备，如扁柏酚的三步合成中所举例说明的（1）。
• Banwell, Martin G.; Cameron, Jennifer M.; Collis, Maree P., Australian Journal of Chemistry, 1991, vol. 44, # 5, p. 705 - 728
  作者：Banwell, Martin G.、Cameron, Jennifer M.、Collis, Maree P.、Crisp, Geoffrey T.、Gable, Robert W.、'et al.

  DOI：——

  日期：——
• 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.

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