4-(triethoxysilyl)-1,2,3-trimethoxybenzene | 869653-86-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(triethoxysilyl)-1,2,3-trimethoxybenzene
• 英文别名: Triethoxy(2,3,4-trimethoxyphenyl)silane；triethoxy-(2,3,4-trimethoxyphenyl)silane
• CAS: 869653-86-1
• 化学式: C₁₅H₂₆O₆Si
• 分子量: 330.453
• InChiKey: GISDPIDGARJGOW-UHFFFAOYSA-N

物化性质

• 沸点：
  350.5±42.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(triethoxysilyl)-1,2,3-trimethoxybenzene 、 溴苯 在 palladium diacetate 四丁基氟化铵 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以70%的产率得到2,3,4-trimethoxybiphenyl
  参考文献：
  名称：

  Efforts Directed toward the Synthesis of Colchicine:  Application of Palladium-Catalyzed Siloxane Cross-Coupling Methodology

  摘要：

  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.

  DOI：

  10.1021/jo051636h
• 作为产物：
  描述：

  硅酸四乙酯 、 1,2,3-三甲氧基苯 以77%的产率得到4-(triethoxysilyl)-1,2,3-trimethoxybenzene
  参考文献：
  名称：

  Efforts Directed toward the Synthesis of Colchicine:  Application of Palladium-Catalyzed Siloxane Cross-Coupling Methodology

  摘要：

  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.

  DOI：

  10.1021/jo051636h

文献信息

• Discovery of structurally simplified analogs of colchicine as an immunosuppressant
  作者：Dong-Jo Chang、Wan-Joo Kim

  DOI：10.1016/j.bmcl.2014.05.007

  日期：2014.7

  We have discovered a new class of colchicine-derived therapeutic agents for immune diseases including rejection of organ-transplantation and autoimmune disease. Compound 2, which had been developed to overcome poor pharmacokinetic properties of compound 1, a first-generation colchicine analog, turned out to show toxicity such as intestinal toxicity and loss of weight during in vivo tests. The deletion of 7-carboxamide group and middle ring-truncation in colchicine allowed us to have structurally simplified analogs with strong immunosuppressive activity. Herein, we report non-alkaloid tricyclic compound 7 and 12 as immunosuppressants which exhibited a strong immunosuppressive in vivo efficacy on the T-dependent antibody response, the Zymosan A-induced arthritis model and the Carrageenan-induced edema model. Compound 7 and 12 revealed less toxicity than the previous lead compound 2, and their minimum lethal doses (MLD) were proved to exceed 100 mg/kg. (C) 2014 Elsevier Ltd. All rights reserved.