2-(2,4-dimethoxy-6-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane | 1028332-18-4

• 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-(2,4-dimethoxy-6-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 1028332-18-4
• 化学式: C₁₅H₂₃BO₄
• 分子量: 278.156
• InChiKey: MIYNQOXFCQSMHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,4-dimethoxy-6-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 2-双环己基膦-2',6'-二甲氧基联苯 、 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium carbonate 、 caesium carbonate 、 lithium hexamethyldisilazane 、 碘甲烷 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 150.0 ℃ 、101.33 kPa 条件下， 反应 50.0h， 生成 7-(2,4-dimethoxy-6-methylphenyl)-2,4-dihydroxy-6,9-dimethoxy-12,12-dimethyltetracen-5(12H)-one
  参考文献：
  名称：

  Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria

  摘要：

  Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (+/-)-naphthacemycin A(9), and (+/-)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.

  DOI：

  10.1021/acs.joc.8b00802
• 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 为溶剂， 反应 16.0h， 生成 2-(2,4-dimethoxy-6-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
  参考文献：
  名称：

  Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria

  摘要：

  Making use of a reductive olefin coupling reaction and Michael-Dieckmann condensation as two key operations, we have completed a concise total synthesis of tetarimycin A, (+/-)-naphthacemycin A(9), and (+/-)-fasamycin A in a highly convergent and practical protocol. Synthetic procedures thus developed have also been applied to provide related analogues for structure-activity relationship studies, thereby coming to the conclusion that the free hydroxyl group at C-10 is essential for exerting inhibitory activities against a panel of Gram-positive bacteria, including drug-resistant strains VRE and MRSA.

  DOI：

  10.1021/acs.joc.8b00802

文献信息

• WO2008/59368
  申请人：——

  公开号：——

  公开（公告）日：——