[(E)-2-(3,5-二甲氧基苯基)乙烯基]硼酸 | 1032737-75-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: [(E)-2-(3,5-二甲氧基苯基)乙烯基]硼酸
• 英文名称: (E)-2-(3,5-dimethoxyphenyl)vinylboronic acid
• 英文别名: 3,5-Dimethoxystyrylboronic Acid；[(E)-2-(3,5-dimethoxyphenyl)ethenyl]boronic acid
• CAS: 1032737-75-9
• 化学式: C₁₀H₁₃BO₄
• 分子量: 208.022
• InChiKey: QTWGCWXQLSVGIM-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.73
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(E)-2-(3,5-二甲氧基苯基)乙烯基]硼酸 在 四(三苯基膦)钯 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 6-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]-3,4-bis(phenylmethoxy)pyridazine
  参考文献：
  名称：

  4-Hydroxypyridazin-3(2H)-one Derivatives as Novel d-Amino Acid Oxidase Inhibitors

  摘要：

  D-Amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including D-serine, a coagonist of the N-methyl-D-aspartate receptor. We identified a series of 4-hydroxypyridazin-3(2H)-one derivatives as novel DAAO inhibitors with high potency and substantial cell permeability using fragment-based drug design. Comparisons of complex structures deposited in the Protein Data Bank as well as those determined with in-house fragment hits revealed that a hydrophobic subpocket was formed perpendicular to the flavin ring by flipping Tyr224 in a ligand-dependent manner. We investigated the ability of the initial fragment hit, 3-hydroxy-pyridine-2(1H)-one, to fill this subpocket with the aid of complex structure information. 3-ydroxy-5-(2-phenylethyl)pyridine-2(1H)-one exhibited the predicted binding mode and demonstrated high inhibitory activity for human DAAO in enzyme- and cell-based assays. We further designed and synthesized 4-hydroxypyridazin-3(2H)-one derivatives, which are equivalent to the 3-hydroxy-pyridine-2(1H)-one series but lack cell toxicity. 6-[2-(3,5-Difluorophenyl)ethyl]-4-hydroxypyridazin-3(2H)-one was found to be effective against MK-801-induced cognitive deficit in the Y-maze.

  DOI：

  10.1021/jm400095b
• 作为产物：
  描述：

  3,5-二甲氧基苯甲醛 在 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 33.0h， 生成 [(E)-2-(3,5-二甲氧基苯基)乙烯基]硼酸
  参考文献：
  名称：

  Synthesis of Novel Resveratrol-Phthalide Hybrid Compounds and Evaluation of Their Inhibitory Activities of Nitric Oxide Production

  摘要：

  DOI：

  10.3987/com-18-s(f)51

文献信息

• Organocatalytic Enantio- and Diastereoselective Synthesis of 1,2-Dihydronaphthalenes from Isobenzopyrylium Ions
  作者：Hui Qian、Wanxiang Zhao、Zhaobin Wang、Jianwei Sun

  DOI：10.1021/ja509824j

  日期：2015.1.21

  efficient asymmetric synthesis of dihydronaphthalenes is disclosed. The process represents a new addition to the limited asymmetric reactions of isobenzopyryliums, a family of versatile 10π-electron aromatic species. Excellent asymmetric induction is achieved for the first time without an anchoring group in the 4-position or a metal catalyst, both of which were required previously in these reactions. The

  公开了二氢萘的高效不对称合成。该过程代表了异苯并吡喃的有限不对称反应的新成员，异苯并吡喃是一个多功能的 10π 电子芳族物种。首次在没有 4 位锚定基团或金属催化剂的情况下实现了出色的不对称诱导，而这两者在这些反应中都是以前需要的。成功归因于从手性磷酸盐和硼酸以及离去基团原位生成的不寻常的手性抗衡阴离子（同时还有亲核试剂）。初步控制实验提供了对反应机制的重要见解。
• Synthesis of Novel Resveratrol-Phthalide Hybrid Compounds and Evaluation of Their Inhibitory Activities of Nitric Oxide Production
  作者：Tetsutaro Kimachi、Satoru Takahashi、Tokutaro Ogata、Misae Doe、Mariko Sakanaka、Arisa Nishiuchi、Mio Aomatsu、Manami Tanaka、Maki Shimizu、Natsuko Yoshioka、Kurumi Kubota、Yui Teraoka、Chikako Nakajima

  DOI：10.3987/com-18-s(f)51

  日期：——
• 4-Hydroxypyridazin-3(2<i>H</i>)-one Derivatives as Novel <scp>d</scp>-Amino Acid Oxidase Inhibitors
  作者：Takeshi Hondo、Masaichi Warizaya、Tatsuya Niimi、Ichiji Namatame、Tomohiko Yamaguchi、Keita Nakanishi、Toshihiro Hamajima、Katsuya Harada、Hitoshi Sakashita、Yuzo Matsumoto、Masaya Orita、Makoto Takeuchi

  DOI：10.1021/jm400095b

  日期：2013.5.9

  D-Amino acid oxidase (DAAO) catalyzes the oxidation of D-amino acids including D-serine, a coagonist of the N-methyl-D-aspartate receptor. We identified a series of 4-hydroxypyridazin-3(2H)-one derivatives as novel DAAO inhibitors with high potency and substantial cell permeability using fragment-based drug design. Comparisons of complex structures deposited in the Protein Data Bank as well as those determined with in-house fragment hits revealed that a hydrophobic subpocket was formed perpendicular to the flavin ring by flipping Tyr224 in a ligand-dependent manner. We investigated the ability of the initial fragment hit, 3-hydroxy-pyridine-2(1H)-one, to fill this subpocket with the aid of complex structure information. 3-ydroxy-5-(2-phenylethyl)pyridine-2(1H)-one exhibited the predicted binding mode and demonstrated high inhibitory activity for human DAAO in enzyme- and cell-based assays. We further designed and synthesized 4-hydroxypyridazin-3(2H)-one derivatives, which are equivalent to the 3-hydroxy-pyridine-2(1H)-one series but lack cell toxicity. 6-[2-(3,5-Difluorophenyl)ethyl]-4-hydroxypyridazin-3(2H)-one was found to be effective against MK-801-induced cognitive deficit in the Y-maze.