3-bromo-5-methoxy-7-methyl-1,4-naphthoquinone | 160465-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-bromo-5-methoxy-7-methyl-1,4-naphthoquinone
• 英文别名: 2-Bromo-8-methoxy-6-methyl-1,4-naphthoquinone；2-bromo-8-methoxy-6-methylnaphthalene-1,4-dione
• CAS: 160465-98-5
• 化学式: C₁₂H₉BrO₃
• 分子量: 281.106
• InChiKey: HFDAFGDBMLSVEX-UHFFFAOYSA-N

物化性质

• 熔点：
  175-177 °C
• 沸点：
  438.1±45.0 °C(Predicted)
• 密度：
  1.604±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-5-methoxy-7-methyl-1,4-naphthoquinone 在 四(三苯基膦)钯 、 铜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 Mamegakinon-dimethylether
  参考文献：
  名称：

  密胺的聚合全合成

  摘要：

  描述了先通过内（非立体异构）轴，然后是两个外（立体异构）轴以高度收敛的方式连续构建而完成的米奇拉明A（1a）和B（1b）的总合成。由于其显着的抗HIV活性，米其敏胺引起了人们的极大兴趣。

  DOI：

  10.1016/s0040-4039(00)78358-4
• 作为产物：
  描述：

  2-溴-8-羟基-6-甲基萘-1,4-二酮 、 碘甲烷 在 silver(l) oxide 作用下， 反应 1.0h， 以97%的产率得到3-bromo-5-methoxy-7-methyl-1,4-naphthoquinone
  参考文献：
  名称：

  密胺的聚合全合成

  摘要：

  描述了先通过内（非立体异构）轴，然后是两个外（立体异构）轴以高度收敛的方式连续构建而完成的米奇拉明A（1a）和B（1b）的总合成。由于其显着的抗HIV活性，米其敏胺引起了人们的极大兴趣。

  DOI：

  10.1016/s0040-4039(00)78358-4

文献信息

• Convergent total synthesis of the michellamines
  作者：T.Ross Kelly、Alberto Garcia、Fengrui Lang、John J. Walsh、K.Vijaya Bhaskar、Michael R. Boyd、Roland Götz、Paul A. Keller、Rainer Walter、Gerhard Bringmann

  DOI：10.1016/s0040-4039(00)78358-4

  日期：1994.10

  The total synthesis of both michellamine A (1a) and B (1b), by consecutive construction first of the inner (non-stereogenic) axis and subsequently the two outer (stereogenic) axes in a highly convergent manner, is described. The michellamines are of considerable interest due to their pronounced anti-HIV activity.

  描述了先通过内（非立体异构）轴，然后是两个外（立体异构）轴以高度收敛的方式连续构建而完成的米奇拉明A（1a）和B（1b）的总合成。由于其显着的抗HIV活性，米其敏胺引起了人们的极大兴趣。
• 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.
• A Convergent Total Synthesis of the Michellamines
  作者：Gerhard Bringmann、Roland Götz、Paul A. Keller、Rainer Walter、Michael R. Boyd、Fengrui Lang、Alberto Garcia、John J. Walsh、Imanol Tellitu、K. Vijaya Bhaskar、T. Ross Kelly

  DOI：10.1021/jo971495m

  日期：1998.2.1

  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.