2.4-二甲氧基-6-甲基苯硼酸 | 202390-71-4

• 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: 2.4-二甲氧基-6-甲基苯硼酸
• 英文名称: 2,4-dimethoxy-6-methylphenylboronic acid
• 英文别名: 2,4-dimethoxy-6-methylphenylboric acid；(2,4-Dimethoxy-6-methylphenyl)boronic acid
• CAS: 202390-71-4
• 化学式: C₉H₁₃BO₄
• mdl: MFCD11111406
• 分子量: 196.011
• InChiKey: ZSGPNFZLMYSDAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  2.4-二甲氧基-6-甲基苯硼酸 、 7-甲氧基-3,4-二氢萘-1-基三氟甲磺酸盐 在 四(三苯基膦)钯 barium dihydroxide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 0.67h， 生成 6-methoxy-4-(2,4-dimethoxy-6-methylphenyl)-1,2-dihydronaphthalene
  参考文献：
  名称：

  Ring Selectivity in the Na/EtOH Reduction of 1-Aryl-7-methoxynaphthalenes

  摘要：

  当1-芳基-7-甲氧基萘的苯基上没有在邻位存在取代基时，Na/EtOH还原反应优先发生在A环（选择性高达100%），生成1-芳基-7-甲氧基-1,2,3,4-四氢萘。而当1-芳基部分的邻位存在取代基时，则偏向于对B环的还原（选择性高达85:15），经乙烯基醚中间体的酸催化水解后，生成相应的8-芳基-2-四氢萘酮。

  DOI：

  10.1055/s-2005-869857
• 作为产物：
  描述：

  3,5-二甲氧基甲苯 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 14.58h， 生成 2.4-二甲氧基-6-甲基苯硼酸
  参考文献：
  名称：

  镍催化 C-OMe 键断裂对苯甲醚衍生物的对映转化

  摘要：

  在此，公开了通过镍催化的C(Ar)-OMe键的动态不对称交叉偶联对苯甲醚衍生物进行对映会聚转化的方案。成功组装了多功能的轴向手性杂联芳基。合成转化证明了该方法的应用潜力。机理研究表明，这种转化的对映体收敛可能是通过非对映体五元氮杂镍环物种的手性配体控制的差向异构化而不是传统的动态动力学拆分来实现的。

  DOI：

  10.1021/jacs.3c05845

文献信息

• Ring Selectivity in the Na/EtOH Reduction of 1-Aryl-7-methoxynaphthalenes
  作者：M. Carreño、Antonio Urbano、Marcos González-López、Alfonso Latorre

  DOI：10.1055/s-2005-869857

  日期：——

  Na/EtOH reduction of 1-aryl-7-methoxynaphthalenes occurred preferentially at the A-ring when no substituents were present at the ortho-positions of the aryl group (up to 100% selectivity), to afford 1-aryl-7-methoxy-1,2,3,4-tetrahydronaphthalenes. Ortho-substitution of the 1-aryl moiety favored B-ring reduction (up to 85:15 selectivity) giving rise, after acidic hydrolysis of the ­vinyl ether intermediate, to the corresponding 8-aryl-2-tetralones.

  当1-芳基-7-甲氧基萘的苯基上没有在邻位存在取代基时，Na/EtOH还原反应优先发生在A环（选择性高达100%），生成1-芳基-7-甲氧基-1,2,3,4-四氢萘。而当1-芳基部分的邻位存在取代基时，则偏向于对B环的还原（选择性高达85:15），经乙烯基醚中间体的酸催化水解后，生成相应的8-芳基-2-四氢萘酮。
• Rational Design and Synthesis of Novel Benzimidazole Derivatives as Potential β-Glucosidase Inhibitors
  作者：Hua Chen、Xu Liu、Ge Sun、Fengxing Li、Xia Feng、Tongguan Jia、Cheng Luo、Shijie Chen

  DOI：10.2174/1570180820666230822141514

  日期：2023.8.22

  potential β-glucosidase inhibitor has been proposed in the previous studies. Objective: A series f new diaryl derivatives linked through benzimidazole have been randomly and rationally designed, synthesized, and evaluated for their inhibitory activities against β-glucosidase (almond). The proposed structural model provides a new strategy for the design of potent β-glucosidase inhibitors. Methods: According

  背景：β-葡萄糖苷酶具有多种生物学功能。先前的研究已经提出了潜在的β-葡萄糖苷酶抑制剂的结构模型。目的：随机合理设计、合成一系列新型苯并咪唑二芳基衍生物，并评价其对β-葡萄糖苷酶（杏仁）的抑制活性。所提出的结构模型为有效的β-葡萄糖苷酶抑制剂的设计提供了新的策略。方法：根据该模型设计合成一系列苯并咪唑衍生物，评价其对β-葡萄糖苷酶（杏仁）的抑制活性、Ki值、抑制类型和结合模式分析（PDB ID：2J7C）。结果：两种化合物7b和7d是最好的抑制剂，IC50值分别为7.86μM和3.52μM。计算出它们的 Ki 值分别为 9.91 μM 和 5.81 μM。结论：SAR分析表明该类苯并咪唑衍生物可能主要通过邻三羟基酚上的氢键与β-葡萄糖苷酶活性位点结合；另一侧朝向溶剂暴露区域的额外苯环对于提高其对β-葡萄糖苷酶的抑制活性起到了非常重要的作用
• A Convergent Total Synthesis of the Michellamines
  作者：Gerhard Bringmann、Roland Götz、Paul A. Keller、Rainer Walter、Michael R. Boyd、Fengrui Lang、Alberto Garcia、John J. Walsh、Imanol Tellitu、K. Vijaya Bhaskar、T. Ross Kelly

  DOI：10.1021/jo971495m

  日期：1998.2.1

  A convergent total synthesis of the anti-HIV michellamines (1) is described. The tetraaryl skeleton of the michellamines mas constructed by formation first of the inner (nonstereogenic) biaryl axis and subsequently of the two other (stereogenic) axes in a highly convergent manner. The key transformation features a double Suzuki-type cross-coupling reaction between binaphthalene ditriflate 26 and isoquinolineboronic acid 35. Ditriflate 26 is synthesized in six steps starting from diene 6 and 2,6-dibromobenzoquinone (9) in 21% overall yield. For large scale production of 26, a substantially shortened version of an existing procedure for the preparation of bisnaphthoquinone 13 was also developed, which allows far the preparation of 13 from benzoquinone and diene 6 in five steps and 67% overall yield. Binaphthoquinone 13 was subsequently converted into ditriflate 26 in three steps and 67% overall yield, By the described synthetic strategy, michellamines A (1a) and B (1b) are produced (1a:1b = 1:2.5) in 24.6% overall yield from diene 6. Curiously, none of the nonnaturally occurring atropoisomer 1c is formed.
• Synthesis and Structure–Activity Relationships of Pyrazolo[1,5-<i>a</i>]pyridine Derivatives: Potent and Orally Active Antagonists of Corticotropin-Releasing Factor 1 Receptor
  作者：Yoshinori Takahashi、Shigeki Hibi、Yorihisa Hoshino、Koichi Kikuchi、Kogyoku Shin、Kaoru Murata-Tai、Masae Fujisawa、Mitsuhiro Ino、Hisashi Shibata、Masahiro Yonaga

  DOI：10.1021/jm300259r

  日期：2012.6.14

  Design, synthesis, and structure activity relationships of a series of 3-dialkylamino-7-phenyl pyrazolo[1,5-a]pyridines (I) as selective antagonists of the corticotropin-releasing factor 1 (CRF1) receptor are described. The most prominent compound to emerge from this work, 46 (E2508), exhibits potent in vitro activity, excellent drug-like properties, and robust oral efficacy in animal models of stress-related disorders. It has advanced into clinical trials.
• PYRAZOLO 1,5-A PYRIDINES AND MEDICINES CONTAINING THE SAME
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1389618B1

  公开（公告）日：2011-06-15