Boronic acid, [2-methyl-4,6-bis(phenylmethoxy)phenyl]- | 202390-74-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Boronic acid, [2-methyl-4,6-bis(phenylmethoxy)phenyl]-
• 英文别名: [2-methyl-4,6-bis(phenylmethoxy)phenyl]boronic acid
• CAS: 202390-74-7
• 化学式: C₂₁H₂₁BO₄
• 分子量: 348.206
• InChiKey: UALNLSHLHVBZHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Acetic acid 1'-acetoxy-8,8'-dimethoxy-6,6'-dimethyl-4,4'-bis-trifluoromethanesulfonyloxy-[2,2']binaphthalenyl-1-yl ester 、 Boronic acid, [2-methyl-4,6-bis(phenylmethoxy)phenyl]- 在 barium dihydroxide 、 四(三苯基膦)钯 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 3.5h， 以88%的产率得到Acetic acid 1'-acetoxy-4,4'-bis-(2,4-bis-benzyloxy-6-methyl-phenyl)-8,8'-dimethoxy-6,6'-dimethyl-[2,2']binaphthalenyl-1-yl ester
  参考文献：
  名称：

  A Convergent Total Synthesis of the Michellamines

  摘要：

  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.

  DOI：

  10.1021/jo971495m

文献信息

• Concise Chemoenzymatic Synthesis of Fasamycin A
  作者：Jian Li、Hans Renata

  DOI：10.1021/acs.joc.1c00526

  日期：2021.8.20

  We report the development of a chemoenzymatic approach toward fasamycin A, a halogenated naphthacenoid that exhibits activities against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus faecalis. The synthesis was accomplished in a convergent manner: two fragments were combined together in a Sammes annulation to afford a dimethylnaphthacenone system. Finally, an enzymatic

  我们报告了针对法沙霉素 A 的化学酶学方法的发展，这是一种卤代环烷烃，对耐甲氧西林金黄色葡萄球菌和耐万古霉素粪肠球菌具有活性。合成以收敛方式完成：两个片段在 Sammes 环中组合在一起以提供二甲基萘酮系统。最后，采用酶促卤化在后期引入天然产物所需的氯取代基。