2-溴-1,5,8-三甲氧基-3-甲基萘 | 189066-68-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-溴-1,5,8-三甲氧基-3-甲基萘
• 英文名称: 2-bromo-1,5,8-trimethoxy-3-methylnaphthalene
• CAS: 189066-68-0
• 化学式: C₁₄H₁₅BrO₃
• 分子量: 311.175
• InChiKey: KOBSPYIURVJVIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  419.2±40.0 °C(Predicted)
• 密度：
  1.364±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-溴-1,5,8-三甲氧基-3-甲基萘 在 四(三苯基膦)钯 正丁基锂 、 ammonium cerium(IV) nitrate 、 硼酸三甲酯 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 15.83h， 生成 diospyrin dimethyl ether
  参考文献：
  名称：

  Synthesis of Diospyrin, a Potential Agent Against Leishmaniasis and Related Parasitic Protozoan Diseases

  摘要：

  The first synthesis of diospyrin [2,6'-bis(5-hydroxy-7-methyl-1,4-naphthoquinone), Ij was achieved by employing Suzuki coupling between 5 and 14 as the key reaction to connect the two 7-methyljuglone units.

  DOI：

  10.1002/1099-0690(200004)2000:7<1313::aid-ejoc1313>3.0.co;2-i
• 作为产物：
  描述：

  4-(乙酰基氧基)-5,8-二甲氧基-2-萘羧酸乙酯 在 lithium aluminium tetrahydride 、 pyridinium hydrobromide perbromide 、 palladium 10% on activated carbon 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 92.0h， 生成 2-溴-1,5,8-三甲氧基-3-甲基萘
  参考文献：
  名称：

  Total Synthesis of the Antitumor–Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer

  摘要：

  The 2,6'-bijuglone natural product diospyrin and its unnatural 3,6'-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methyljuglone) and include a key Suzuki-Miyaura cross-coupling. Diospyrin, idospyrin, and several synthetic precursors exhibit potent and selective cytotoxicity to the murine myeloma NS-1 cell line over neonatal foreskin cells.

  DOI：

  10.1021/acs.jnatprod.0c00800

文献信息

• Synthesis and Absolute Configuration of Axially Chiral Binaphthoquinones
  作者：Robert W. Baker、Song Liu、Melvyn V. Sargent

  DOI：10.1071/c97088

  日期：——

  The synthesis of (+)-(S)-1′,4-dihydroxy-2,3′-dimethyl-1,2′-binaphthalene-5,5′,8,8′-tetrone (62) and (+)-(S)-4,5′,8′-trihydroxy-2,3′-dimethyl-1,2′-binaphthalene-1′,4′,5,8-tetrone (55), compounds which are atrop-isomeric with the naturally occurring binaphthoquinones (–)-isodiospyrin and (–)-8′-hydroxyisodiospyrin, respectively, is described. The binaphthyl linkages in these compounds were stereoselectively constructed by using oxazoline chemistry. The stereochemical assignments were based on X-ray crystal structure determination and circular dichroic spectroscopy.

  合成 (+)-(S)-1′,4-二羟基-2,3′-二甲基-1,2′-萘-5,5′,8,8′-四酮(62)的合成 (62)和 (+)-(S)-4,5′,8′-三羟基-2,3′-二甲基-1,2′-萘-1′,4′,5,8-四酮(55)。 (55），这些化合物与天然存在的 (-)-isodiospyrin 和 (-)-8′-hydroxyisodiospyrin 的异构体。这些 中的二萘基连接是通过噁唑啉化学方法立体选择性地构建的。 使用噁唑啉化学方法立体选择性地构建了这些化合物中的二萘基连接。立体化学分配基于 X 射线 晶体结构测定和圆二色光谱测定。
• Synthesis of Diospyrin, a Potential Agent Against Leishmaniasis and Related Parasitic Protozoan Diseases
  作者：Masao Yoshida、Kenji Mori

  DOI：10.1002/1099-0690(200004)2000:7<1313::aid-ejoc1313>3.0.co;2-i

  日期：2000.4

  The first synthesis of diospyrin [2,6'-bis(5-hydroxy-7-methyl-1,4-naphthoquinone), Ij was achieved by employing Suzuki coupling between 5 and 14 as the key reaction to connect the two 7-methyljuglone units.
• Total Synthesis of the Antitumor–Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer
  作者：Glenn A. Pullella、Daniel Vuong、Ernest Lacey、Matthew J. Piggott

  DOI：10.1021/acs.jnatprod.0c00800

  日期：2020.12.24

  The 2,6'-bijuglone natural product diospyrin and its unnatural 3,6'-isomer idospyrin have been synthesized in seven steps each from N,N-diethylsenecioamide in overall yields of 12% and 13%, respectively. The syntheses diverge from ramentaceone (7-methyljuglone) and include a key Suzuki-Miyaura cross-coupling. Diospyrin, idospyrin, and several synthetic precursors exhibit potent and selective cytotoxicity to the murine myeloma NS-1 cell line over neonatal foreskin cells.