5-Methoxy-7-methyl-5-trimethylsilanyloxy-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone | 202390-66-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Methoxy-7-methyl-5-trimethylsilanyloxy-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
• 英文别名: 8-methoxy-6-methyl-8-trimethylsilyloxy-5,8a-dihydro-4aH-naphthalene-1,4-dione
• CAS: 202390-66-7
• 化学式: C₁₅H₂₂O₄Si
• 分子量: 294.423
• InChiKey: GXKQQXCAGUJMHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Methoxy-7-methyl-5-trimethylsilanyloxy-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 7-甲基-5-羟基萘醌
  参考文献：
  名称：

  A Convergent Total Synthesis of the Michellamines

  摘要：

  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.

  DOI：

  10.1021/jo971495m
• 作为产物：
  描述：

  1-methoxy-3-methyl-1-trimethylsilyloxy-1,3-butadiene 、 对苯醌 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 5-Methoxy-7-methyl-5-trimethylsilanyloxy-4a,5,8,8a-tetrahydro-[1,4]naphthoquinone
  参考文献：
  名称：

  A Convergent Total Synthesis of the Michellamines

  摘要：

  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.

  DOI：

  10.1021/jo971495m

文献信息

• 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.