Acetic acid 4,1',4'-triacetoxy-8,8'-dimethoxy-6,6'-dimethyl-[2,2']binaphthalenyl-1-yl ester | 160465-99-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Acetic acid 4,1',4'-triacetoxy-8,8'-dimethoxy-6,6'-dimethyl-[2,2']binaphthalenyl-1-yl ester
• 英文别名: [4-Acetyloxy-3-(1,4-diacetyloxy-8-methoxy-6-methylnaphthalen-2-yl)-5-methoxy-7-methylnaphthalen-1-yl] acetate
• CAS: 160465-99-6
• 化学式: C₃₂H₃₀O₁₀
• 分子量: 574.584
• InChiKey: SFJQATPJGJFJHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid 4,1',4'-triacetoxy-8,8'-dimethoxy-6,6'-dimethyl-[2,2']binaphthalenyl-1-yl ester 在 2,6-二甲基吡啶 、 barium dihydroxide 、 四(三苯基膦)钯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 、 水 为溶剂， 反应 3.92h， 生成 Acetic acid 1'-acetoxy-4,4'-bis-(2,4-bis-benzyloxy-6-methyl-phenyl)-8,8'-dimethoxy-6,6'-dimethyl-[2,2']binaphthalenyl-1-yl ester
  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：

  4,8-二甲氧基-6-甲基萘-1-醇 在 4-二甲氨基吡啶 、 硝酸 、 sodium acetate 、 三乙胺 、 silver(l) oxide 、 锌 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 44.03h， 生成 Acetic acid 4,1',4'-triacetoxy-8,8'-dimethoxy-6,6'-dimethyl-[2,2']binaphthalenyl-1-yl ester
  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

• 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。
• Structural analogues of the michellamine anti-HIV agents. Importance of the tetrahydroisoquinoline rings for biological activity
  作者：Heping Zhang、David E Zembower、Zhidong Chen

  DOI：10.1016/s0960-894x(97)10057-9

  日期：1997.10

  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.