2-methoxybiphenyl-3-carbaldehyde | 81948-59-6

• 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-methoxybiphenyl-3-carbaldehyde
• 英文别名: 2-methoxy-3-phenylbenzaldehyde
• CAS: 81948-59-6
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: TVDYLKSDOVQCEL-UHFFFAOYSA-N

物化性质

• 熔点：
  53-54 °C(Solv: methanol (67-56-1))
• 沸点：
  338.5±30.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methoxybiphenyl-3-carbaldehyde 在 vanadium(III) chloride 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-(2-methoxybiphenyl-3-yl)ethanone
  参考文献：
  名称：

  Development of Serine Protease Inhibitors Displaying a Multicentered Short (<2.3 Å) Hydrogen Bond Binding Mode:  Inhibitors of Urokinase-Type Plasminogen Activator and Factor Xa

  摘要：

  Novel scaffolds that bind to serine proteases through a unique network of short hydrogen bonds to the catalytic Ser195 have been developed. The resulting potent serine protease inhibitors were designed from lead molecule 2-(2-hydroxyphenyl)1H-benzoimidazole-5-carboxamidine, 6b, which is known to display several modes of binding. For instance, 6b can recruit zinc and bind in a manner similar to that reported by bis(5-amidino-2-benzimidazolyl)methane (BABIM) (Nature 1998, 391, 608-612).(1) Alternatively, 6b can bind in the absence of zinc through a multicentered network of short (<2.3 Angstrom) hydrogen bonds. The lead structure was optimized in the zinc-independent binding mode toward a panel of six human serine proteases to yield optimized inhibitors such as 2-(3-bromo-2-hydroxy-5-methylphenyl)-1H-indole-5-carboxamidine, 22a, and 2-(2-hydroxybiphenyl-3-yl)-1H-indole-5-carboxamidine, 22f. Structure-activity relationships determined that, apart from the amidine function, an indole or benzimidazole and an ortho substituted phenol group were also essential components for optimal potency. The affinities (K-i) of 22a and 22f, for example, bearing these groups ranged from 8 to 600 nM toward a panel of six human serine proteases. High-resolution crystal structures revealed that the binding mode of these molecules in several of the enzymes was identical to that of 6b and involved short (<2.3 Angstrom) hydrogen bonds among the inhibitor hydroxyl oxygen, Ser195, and a water molecule trapped in the oxyanion hole. In summation, novel and potent trypsin-like serine protease inhibitors possessing a unique mode of binding have been discovered.

  DOI：

  10.1021/jm0100638
• 作为产物：
  描述：

  邻苯基苯酚 、 alkaline earth salt of/the/ methylsulfuric acid 在 caesium carbonate 、 三乙胺 、 magnesium chloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-methoxybiphenyl-3-carbaldehyde
  参考文献：
  名称：

  Development of Serine Protease Inhibitors Displaying a Multicentered Short (<2.3 Å) Hydrogen Bond Binding Mode:  Inhibitors of Urokinase-Type Plasminogen Activator and Factor Xa

  摘要：

  Novel scaffolds that bind to serine proteases through a unique network of short hydrogen bonds to the catalytic Ser195 have been developed. The resulting potent serine protease inhibitors were designed from lead molecule 2-(2-hydroxyphenyl)1H-benzoimidazole-5-carboxamidine, 6b, which is known to display several modes of binding. For instance, 6b can recruit zinc and bind in a manner similar to that reported by bis(5-amidino-2-benzimidazolyl)methane (BABIM) (Nature 1998, 391, 608-612).(1) Alternatively, 6b can bind in the absence of zinc through a multicentered network of short (<2.3 Angstrom) hydrogen bonds. The lead structure was optimized in the zinc-independent binding mode toward a panel of six human serine proteases to yield optimized inhibitors such as 2-(3-bromo-2-hydroxy-5-methylphenyl)-1H-indole-5-carboxamidine, 22a, and 2-(2-hydroxybiphenyl-3-yl)-1H-indole-5-carboxamidine, 22f. Structure-activity relationships determined that, apart from the amidine function, an indole or benzimidazole and an ortho substituted phenol group were also essential components for optimal potency. The affinities (K-i) of 22a and 22f, for example, bearing these groups ranged from 8 to 600 nM toward a panel of six human serine proteases. High-resolution crystal structures revealed that the binding mode of these molecules in several of the enzymes was identical to that of 6b and involved short (<2.3 Angstrom) hydrogen bonds among the inhibitor hydroxyl oxygen, Ser195, and a water molecule trapped in the oxyanion hole. In summation, novel and potent trypsin-like serine protease inhibitors possessing a unique mode of binding have been discovered.

  DOI：

  10.1021/jm0100638

文献信息

• Thrombopoietin mimetics
  申请人：——

  公开号：US20030083361A1

  公开（公告）日：2003-05-01

  Invented are non-peptide TPO mimetics. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected substituted naphthimidazole derivative.

  发明了非肽类TPO类似物。还发明了一种治疗血小板减少症的方法，包括在需要的哺乳动物，包括人类中，向该哺乳动物施用所选取代萘咪唑衍生物的有效量。
• 遷移金属化合物、オレフィン多量化用触媒およびオレフィン多量体の製造方法
  申请人：三井化学株式会社

  公开号：JP2018162230A

  公开（公告）日：2018-10-18

  【課題】新規な遷移金属化合物、その化合物を含有する優れた活性、選択性を有するオレフィン多量化用触媒、およびそのオレフィン多量化用触媒の存在下で行うオレフィン多量体の製造方法を提供する。【解決手段】一般式(1)の遷移金属化合物、これを含むオレフィン多量化用触媒及びこの触媒を用いたオレフィン多量体の製造方法（R1〜R6は水素原子等、Mは周期律表第6族の遷移金属原子、nはMの原子価、Xはハロゲン原子等、Yは酸素原子等、Zは炭化水素基等、Ｑは置換基を有する酸素原子等）。 【化１】【選択図】なし

  提供新型过渡金属化合物、具有优良活性和选择性的烯烃多聚化用催化剂，以及在该烯烃多聚化用催化剂存在下进行烯烃多聚体制备的方法。一般式（1）的过渡金属化合物，包括这种化合物的烯烃多聚化用催化剂，以及利用该催化剂制备烯烃多聚体的方法（其中R1〜R6为氢原子等，M为周期表第6族的过渡金属原子，n为M的原子价，X为卤素原子等，Y为氧原子等，Z为烃基等，Q为带有取代基的氧原子等）。【化1】【选择图】无
• Catalyst Compounds and Use Thereof
  申请人：Giesbrecht Garth R.

  公开号：US20110098425A1

  公开（公告）日：2011-04-28

  This invention relates to Group 4 catalyst compounds containing di-anionic tridentate nitrogen/oxygen based ligands. The catalyst compounds are useful, with or without activators, to polymerize olefins, particularly a-olefins, or other unsaturated monomers. Systems and processes to oligomerize and/or polymerize one or more unsaturated monomers using the catalyst compound, as well as the oligomers and/or polymers produced therefrom are also provided.

  这项发明涉及含有双阴离子三齿氮/氧基配体的第四族催化剂化合物。这些催化剂化合物在有或没有活化剂的情况下，用于聚合烯烃，特别是α-烯烃，或其他不饱和单体。还提供了使用该催化剂化合物寡聚和/或聚合一个或多个不饱和单体的系统和工艺，以及由此产生的寡聚物和/或聚合物。
• Synthesis of Diphenyl-substituted Flavonoid Compounds on Both Benzene Rings
  作者：Hisashi Matsumura、Toshio Tsuchiya、Kimiaki Imafuku

  DOI：10.1246/bcsj.56.3519

  日期：1983.11

  Condensation of o-hydroxyacetophenone and its 3- and 5-phenyl-substituted compounds with 2- or 4-methoxy-biphenyl-3-carbaldehyde gave six mono- and diphenyl-substituted 2′-hydroxychalcones (5a–f), which were cyclized with alkali to afford the flavanones. The chalcones 5a–f were also converted to the corresponding flavones via chalcone bromides.

  邻羟基苯乙酮及其 3- 和 5-苯基取代的化合物与 2- 或 4-甲氧基-联苯-3- 甲醛缩合得到六个单-和二苯基-取代的 2'-羟基查尔酮 (5a-f)，它们被环化用碱得到黄烷酮。查耳酮 5a-f 也通过查耳酮溴化物转化为相应的黄酮。
• Naphthimidazole derivatives and their use as thrombopoietin mimetics
  申请人：Luengo Juan I.

  公开号：US06858630B2

  公开（公告）日：2005-02-22

  Invented are non-peptide TPO mimetics. Also invented is a method of treating thrombocytopenia, in a mammal, including a human, in need thereof which comprises administering to such mammal an effective amount of a selected substituted naphthimidazole derivative.

  发明了非肽类 TPO 模拟剂。还发明了一种治疗血小板减少症的方法，包括在需要的哺乳动物中，包括人类，向该哺乳动物施用所选的取代萘咪唑衍生物的有效量。