(E)-4,4',8,8'-tetramethoxy-6,6'-dimethyl-1H,1'H-[2,2'-binaphthalenylidene]-1,1'-dione | 75445-89-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-4,4',8,8'-tetramethoxy-6,6'-dimethyl-1H,1'H-[2,2'-binaphthalenylidene]-1,1'-dione
• 英文别名: (2E)-2-(4,8-dimethoxy-6-methyl-1-oxonaphthalen-2-ylidene)-4,8-dimethoxy-6-methylnaphthalen-1-one
• CAS: 75445-89-5
• 化学式: C₂₆H₂₄O₆
• 分子量: 432.473
• InChiKey: VMZNAYZFRQCQHT-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-4,4',8,8'-tetramethoxy-6,6'-dimethyl-1H,1'H-[2,2'-binaphthalenylidene]-1,1'-dione 在 硝酸 作用下， 以 氯仿 为溶剂， 反应 0.53h， 生成 7,12-Dihydro-5-hydroxy-1,8-dimethoxy-3,10-dimethyldinaphtho<2,3-b;2',1'-d>furan-7,12-dion
  参考文献：
  名称：

  Laatsch, Hartmut, Liebigs Annalen der Chemie, 1980, # 8, p. 1321 - 1347

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯-3-甲基苯酚 在 10% palladium on active carbon 盐酸 、 sodium hydroxide 、 三氯化铝 、 sodium dithionite 、 水 、 氢气 、 sodium acetate 、 三乙胺 、 sodium chloride 、 silver(l) oxide 、 锌 作用下， 以 吡啶 、 甲醇 、 乙醚 、 氯仿 、 水 为溶剂， 反应 19.25h， 生成 (E)-4,4',8,8'-tetramethoxy-6,6'-dimethyl-1H,1'H-[2,2'-binaphthalenylidene]-1,1'-dione
  参考文献：
  名称：

  Laatsch, Hartmut, Liebigs Annalen der Chemie, 1980, # 8, p. 1321 - 1347

  摘要：

  DOI：

文献信息

• Hypoiodite-catalysed oxidative homocoupling of arenols and tandem oxidation/cross-coupling of hydroquinones with arenes
  作者：Muhammet Uyanik、Dai Nagata、Kazuaki Ishihara

  DOI：10.1039/d1cc05171g

  日期：——

  We report the hypoiodite-catalyzed oxidative C–C homocoupling of arenols to biarenols or biquinones using aqueous hydrogen peroxide as an oxidant. In addition, by combining hypoiodite catalysis and lipophilic Lewis acid-assisted Brønsted acid catalysis under aqueous conditions, we achieved a tandem oxidation/cross-coupling reaction of hydroquinones with electron-rich arenes. These results highlight

  我们报告了使用过氧化氢水溶液作为氧化剂的次碘酸盐催化氧化 C-C 同偶联的壬醇与双烯醇或双醌。此外，通过在水性条件下结合次碘酸盐催化和亲脂性路易斯酸辅助布朗斯台德酸催化，我们实现了对苯二酚与富电子芳烃的串联氧化/交叉偶联反应。这些结果突出了次碘酸盐/酸共催化在氧化偶联反应中的应用范围。
• 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.
• 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.
• Laatsch, Hartmut, Liebigs Annalen der Chemie, 1980, # 8, p. 1321 - 1347
  作者：Laatsch, Hartmut

  DOI：——

  日期：——