1,2,3,4-tetrahydro-5,7-dimethoxy-1,1-dimethylnaphthalene | 156868-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1,2,3,4-tetrahydro-5,7-dimethoxy-1,1-dimethylnaphthalene
• 英文别名: 6,8-dimethoxy-4,4-dimethyl-2,3-dihydro-1H-naphthalene
• CAS: 156868-47-2
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: XQXJCTLWOOCPBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-5,7-dimethoxy-1,1-dimethylnaphthalene 在 叔丁基过氧化氢 、 copper(l) iodide 、 palladium 10% on activated carbon 、 三溴化硼 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 44.0h， 生成 tetarimycin A
  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：

  4-(2,4-dimethoxy-phenyl)-4-oxo-butyric acid methyl ester 在 palladium on activated charcoal 盐酸 、 水 、 氢气 作用下， 以 甲醇 、 乙醚 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 28.0h， 生成 1,2,3,4-tetrahydro-5,7-dimethoxy-1,1-dimethylnaphthalene
  参考文献：
  名称：

  四氢萘的合成。第二部分

  摘要：

  描述了利用环脱水方法的合成，以制备在芳香环的每个位置上被官能团取代并且在非芳香环的1-位上被多个烷基取代的新型四氢萘。

  DOI：

  10.1016/s0040-4020(01)87011-3

文献信息

• Studies on Antibiotics Active against Resistant Bacteria. Total Synthesis of MRSA-Active Tetarimycin A and Its Analogues
  作者：Jing-Kai Huang、Tsai-Ling Yang Lauderdale、Kak-Shan Shia

  DOI：10.1021/acs.orglett.5b02039

  日期：2015.9.4

  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.
• Synthesis and Herbicidal Activity of Substituted Tetrahydronaphthalenes (Part II)
  作者：John J. Parlow、Martin D. Mahoney

  DOI：10.1002/(sici)1096-9063(199603)46:3<227::aid-ps358>3.0.co;2-v

  日期：1996.3

  This paper reports the synthesis and the biological activity of novel tetrahydronaphthalenes with substitution of functional groups at each position of the aromatic ring and substitution of various alkyl groups at the 1-position of the non-aromatic ring. These compounds exhibited pre-emergent herbicidal activity which was determined by the orientation and type of functional groups on the aromatic ring with the 1,1-dimethyl substitution on the non-aromatic ring. The activity tended to be highest for nitro or methyl at the 5- and 7-positions with an amino or ester group at the 6-position and a dimethyl substitution at the 1-position.
• Syntheses of tetrahydronaphthalenes. Part II
  作者：John J. Parlow

  DOI：10.1016/s0040-4020(01)87011-3

  日期：1994.3

  Syntheses utilizing the cyclodehydration method to prepare novel tetrahydronaphthalenes substituted with functional groups at each position of the aromatic ring and various alkyl groups at the 1-position of the non-aromatic ring are described.

  描述了利用环脱水方法的合成，以制备在芳香环的每个位置上被官能团取代并且在非芳香环的1-位上被多个烷基取代的新型四氢萘。
• 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.