6,8-dimethoxy-4,4-dimethylnaphthalen-1(4H)-one | 120078-32-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6,8-dimethoxy-4,4-dimethylnaphthalen-1(4H)-one
• 英文别名: 6,8-Dimethoxy-4,4-dimethyl-1(4H)-naphthalenone；6,8-dimethoxy-4,4-dimethylnaphthalen-1-one
• CAS: 120078-32-2
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: JQAYKTZSXMHPCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6,8-dimethoxy-4,4-dimethylnaphthalen-1(4H)-one 、 4-(2,4-dimethoxy-6-methylphenyl)-6-methoxy-3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile 在 lithium tert-butoxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.75h， 生成
  参考文献：
  名称：

  Synthesis of (±)-Naphthacemycin A₉

  摘要：

  Naphthacemycin A(9) was synthesized in nine steps by a sequence featuring a Diels-Alder reaction of a hindered aryl butadiene and a Hauser-Kraus annulation reaction.

  DOI：

  10.1021/acs.joc.8b02658
• 作为产物：
  描述：

  4-(2,4-二甲氧基-苯基)-4-氧代丁酸 在 三乙基硅烷 、 叔丁基过氧化氢 、 copper(l) iodide 、 potassium carbonate 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 20.0h， 生成 6,8-dimethoxy-4,4-dimethylnaphthalen-1(4H)-one
  参考文献：
  名称：

  Studies on Antibiotics Active against Resistant Bacteria. Total Synthesis of MRSA-Active Tetarimycin A and Its Analogues

  摘要：

  Making use of the Hauser-Kraus annulation as a key step, the first total synthesis of tetarimycin A has been accomplished in a highly convergent and operationally simple manner. Preliminary SAR not only validated that tetarimycin A exhibited potent activity against MRSA and VRE at a low MIC value but also identified that the hydroxyl group at C-10 was essential for antibacterial activities.

  DOI：

  10.1021/acs.orglett.5b02039

文献信息

• Total Synthesis of Tetarimycin A, (±)-Naphthacemycin A₉, and (±)-Fasamycin A: Structure–Activity Relationship Studies against Drug-Resistant Bacteria
  作者：Jing-Kai Huang、Tsai-Ling Yang Lauderdale、Chun-Cheng Lin、Kak-Shan Shia

  DOI：10.1021/acs.joc.8b00802

  日期：2018.6.15

  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.