2,3,4-trimethoxybiphenyl | 95127-11-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3,4-trimethoxybiphenyl
• 英文别名: Trimethoxybiphenyl；1,2,3-trimethoxy-4-phenylbenzene
• CAS: 95127-11-0
• 化学式: C₁₅H₁₆O₃
• 分子量: 244.29
• InChiKey: WHBMTTKYTPHVIO-UHFFFAOYSA-N

物化性质

• 熔点：
  46.5 °C
• 沸点：
  128-132 °C(Press: 0.5 Torr)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2,3,4-trimethoxybiphenyl 在 三氯化铝 、 氯苯 作用下， 生成 4-苯基苯-1,2,3-三醇
  参考文献：
  名称：

  聚羟基联苯系列的合成和氧化研究。第一部分

  摘要：

  DOI：

  10.1039/jr9550004435
• 作为产物：
  描述：

  1,2,3-三甲氧基苯 在 四丁基氟化铵 、 乙酸酐 、 三氯化铁 、 pyridinium hydrobromide perbromide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 2-(二环己基膦基)联苯 作用下， 以 四氢呋喃 为溶剂， 反应 6.25h， 生成 2,3,4-trimethoxybiphenyl
  参考文献：
  名称：

  Palladium-Catalyzed Cross-Coupling of Aryl Triethylammonium Bis(catechol) Silicates with Aryl Bromides Using Microwave Irradiation

  摘要：

  The scope of the palladium-catalyzed cross-coupling reaction of aryl bis(catechol) silicates has been extended to include the coupling of aryl bromides by employing microwave irradiation. This new set of coupling conditions is tolerant of electron-rich and -deficient aryl bromides. In addition, a variety of substituted aryl bis(catechol) silicates have been successfully cross-coupled.

  DOI：

  10.1021/ol048044q

文献信息

• Palladium catalysed coupling of halobenzenes with arylboronic acids: Rôle of the triphenylphosphine ligand
  作者：David F. O'Keefe、Megan C. Dannock、Sebastian M. Marcuccio

  DOI：10.1016/s0040-4039(00)61017-1

  日期：1992.10

  The synthesis of unsymmetrically substituted biaryls via palladium catalysed coupling of aryl halides with arylboronic acids was found to produce biaryl by-products where one aryl was derived from the triphenylphosphine ligand. The use of substituted triphenylphosphine ligands to minimise this side reaction was investigated.

  发现通过钯催化的芳基卤化物与芳基硼酸的偶联来合成不对称取代的联芳基会产生联芳副产物，其中一个芳基衍生自三苯基膦配体。研究了使用取代的三苯基膦配体以最小化该副反应。
• Cobalt-Catalyzed Coupling of Aryl Chlorides with Aryl Boron Esters Activated by Alkoxides
  作者：Sanita B. Tailor、Mattia Manzotti、Gavin J. Smith、Sean A. Davis、Robin B. Bedford

  DOI：10.1021/acscatal.0c05557

  日期：2021.4.2

  cobalt-catalyzed Suzuki biaryl cross-coupling of aryl chloride substrates with aryl boron reagents, activated with more commonly used bases, remained a significant unmet challenge in the race to replace platinum group metal catalysts with Earth-abundant metal alternatives. We now show that this highly desirable process can be realized using alkoxide bases, provided the right counterion is employed, strict

  用更常用的碱活化的芳基氯化物与芳基硼试剂的钴催化的Suzuki联芳基交叉偶联，在用地球上富集的金属替代物取代铂族金属催化剂的竞赛中，仍然是一项重大的未解决的挑战。现在我们表明，只要使用正确的抗衡离子，对芳基硼试剂保持严格的碱化学计量控制，并选择正确的硼酸酯，就可以使用醇盐碱实现这一高度理想的方法。钾叔丁醇的效果很好，但基座第一抑制的任何多余的，然后使催化剂中毒。锂叔丁醇的性能非常差，而即使催化量的锂添加剂也会使催化剂中毒。同时，为了获得最佳性能，需要新戊烷二醇基硼酸酯。除了提供这种广受欢迎的转化方法之外，我们还进行了详细的机理和计算研究，以探究反应的可能机理并帮助解释意想不到的实验观察结果。
• Inhibitors of Histone Deacetylase
  申请人：Moradei Oscar

  公开号：US20080132503A1

  公开（公告）日：2008-06-05

  The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.

  本发明涉及抑制组蛋白去乙酰化酶。本发明提供了抑制组蛋白去乙酰化酶酶活性的化合物和方法。本发明还提供了治疗细胞增殖性疾病和病症的组合物和方法。
• Efforts Directed toward the Synthesis of Colchicine:  Application of Palladium-Catalyzed Siloxane Cross-Coupling Methodology
  作者：W. Michael Seganish、Christopher J. Handy、Philip DeShong

  DOI：10.1021/jo051636h

  日期：2005.10.1

  Colchicine is an important and synthetically challenging natural product. The key synthetic step in this approach to the synthesis of colchicine involved a palladium-catalyzed cross-coupling reaction between 5-bromotropolone (4) and an aryl siloxane to form the aryl-tropolone bond. The coupling of a variety of highly functionalized aryl siloxane derivatives was investigated and optimized coupling conditions were developed. It was discovered that a palladium catalyst with a high degree of phosphine ligand coordination (5 equiv of phosphine/mol Pd) was necessary to efficiently couple aryl siloxanes with 5-bromotropolone (4). In addition, the coupling approach has provided a direct comparison between siloxane and boronic acid coupling technologies that demonstrated that aryl siloxanes and boronic acids produce similar yields of highly functionalized biaryl products.
• Synthesis, x-ray crystal structure, and antimitotic properties of 6-chloro-2-methoxy-5-(2',3',4'-trimethoxyphenyl)cyclohepta-2,4,6-trien-1-one, a bicyclic analog of colchicine
  作者：Martin G. Banwell、Kathleen A. Herbert、John R. Buckleton、George R. Clark、Clifton E. F. Rickard、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jo00256a009

  日期：1988.10