Acetic acid 1'-acetoxy-8,8'-dimethoxy-6,6'-dimethyl-4,4'-bis-trifluoromethanesulfonyloxy-[2,2']binaphthalenyl-1-yl ester | 160466-00-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Acetic acid 1'-acetoxy-8,8'-dimethoxy-6,6'-dimethyl-4,4'-bis-trifluoromethanesulfonyloxy-[2,2']binaphthalenyl-1-yl ester
• 英文别名: [2-[1-Acetyloxy-8-methoxy-6-methyl-4-(trifluoromethylsulfonyloxy)naphthalen-2-yl]-8-methoxy-6-methyl-4-(trifluoromethylsulfonyloxy)naphthalen-1-yl] acetate
• CAS: 160466-00-2
• 化学式: C₃₀H₂₄F₆O₁₂S₂
• 分子量: 754.636
• InChiKey: CWWONUJFYZUSKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  175
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  Acetic acid 1'-acetoxy-8,8'-dimethoxy-6,6'-dimethyl-4,4'-bis-trifluoromethanesulfonyloxy-[2,2']binaphthalenyl-1-yl ester 在 palladium on activated charcoal 盐酸 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 barium dihydroxide 、 氢气 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4,4'-Bis-(2,4-dihydroxy-phenyl)-8,8'-dimethoxy-6,6'-dimethyl-[2,2']binaphthalenyl-1,1'-diol
  参考文献：
  名称：

  Structural analogues of the michellamine anti-HIV agents. Importance of the tetrahydroisoquinoline rings for biological activity

  摘要：

  A series of michellamine structural analogues was prepared in which the tetrahydroisoquinoline rings were substituted with a variety of simple aromatic ring systems. Additionally, the methyl groups on the central bis-naphthalene cores were replaced with hydrogen and methoxy. All the analogues were devoid of anti-HIV activity, suggesting that the heterocyclic portion of the tetrahydroisoquinoline ring is crucial for biological activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10057-9
• 作为产物：
  描述：

  4,8-二甲氧基-6-甲基萘-1-醇 在 4-二甲氨基吡啶 、 硝酸 、 sodium acetate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 silver(l) oxide 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 0.03h， 生成 Acetic acid 1'-acetoxy-8,8'-dimethoxy-6,6'-dimethyl-4,4'-bis-trifluoromethanesulfonyloxy-[2,2']binaphthalenyl-1-yl ester
  参考文献：
  名称：

  Structural analogues of the michellamine anti-HIV agents. Importance of the tetrahydroisoquinoline rings for biological activity

  摘要：

  A series of michellamine structural analogues was prepared in which the tetrahydroisoquinoline rings were substituted with a variety of simple aromatic ring systems. Additionally, the methyl groups on the central bis-naphthalene cores were replaced with hydrogen and methoxy. All the analogues were devoid of anti-HIV activity, suggesting that the heterocyclic portion of the tetrahydroisoquinoline ring is crucial for biological activity. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10057-9

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。
• Octadehydromichellamine, a structural analog of the anti-HIV michellamines without centrochirality
  作者：Gerhard Bringmann、Matthias Wenzel、T.Ross Kelly、Michael R. Boyd、Robert J. Gulakowski、Ronald Kaminsky

  DOI：10.1016/s0040-4020(98)01195-8

  日期：1999.2

  octadehydromichellamine (4), as the fully dehydrogenated structural analog of the naturally occurring michellamines (1), is described. This derivative is the first michellamine-type quateraryl without centrochirality and thus constitutes a distinctly simplified structural michellamine analog. Key step of the total synthesis is the twofold coupling of a bis-O-triflate activated central binaphthalene building

  描述了作为天然存在的蜜三胺（1）的完全脱氢的结构类似物的十八氢蜜三胺（4）的合成。该衍生物是第一个没有中心酸的米切尔敏型四杂芳基，因此构成了结构明显简化的米切尔敏类似物。总合成的关键步骤是双-O-三氟甲磺酸盐活化的中心双萘结构单元9与2eq。的双重偶联。异喹啉硼酸8的“α ”生成明显的立体化学纯形式的季戊基芳基11，其脱保护基团递送目标分子4。十八氢次氯胺酮（4）显示出良好的抗HIV活性，并且与天然michellamines相比，对恶性疟原虫的抗疟活性增强。
• 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.