2,3,4,4a-tetrahydro-6,8-dimethoxy-1,1,4a-trimethyl-1H-fluorene | 1148136-43-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2,3,4,4a-tetrahydro-6,8-dimethoxy-1,1,4a-trimethyl-1H-fluorene
• 英文别名: 6,8-dimethoxy-1,1,4a-trimethyl-2,3,4,4a-tetrahydro-1H-fluorene；6,8-dimethoxy-1,1,4a-trimethyl-3,4-dihydro-2H-fluorene
• CAS: 1148136-43-9
• 化学式: C₁₈H₂₄O₂
• 分子量: 272.387
• InChiKey: NKYTUSCSPXKNEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4,4a-tetrahydro-6,8-dimethoxy-1,1,4a-trimethyl-1H-fluorene 在 正丁基锂 、 四甲基乙二胺 、 丙酮 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 14.0h， 以12%的产率得到2,3,4,4a-tetrahydro-6,8-dimethoxy-1,1,4a-trimethyl-1H-fluoren-7-ol
  参考文献：
  名称：

  Synthesis of 5-epi-Taiwaniaquinone G

  摘要：

  A concise synthetic approach to the unnatural 5-epi-taiwaniaquinone G has been developed via a Lewis acid catalyzed tandem acylation-Nazarov cyclization reaction to construct the tricyclic skeleton, followed by installation of the isopropyl group through a strategy involving coumarin formation and its subsequent hydrolysis.

  DOI：

  10.1021/jo500931e
• 作为产物：
  描述：

  2,6,6-三甲基环己烯-1-羧酸 在 lithium aluminium tetrahydride 、 三氟乙酸酐 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 12.0h， 生成 2,3,4,4a-tetrahydro-6,8-dimethoxy-1,1,4a-trimethyl-1H-fluorene
  参考文献：
  名称：

  Synthesis of 5-epi-Taiwaniaquinone G

  摘要：

  A concise synthetic approach to the unnatural 5-epi-taiwaniaquinone G has been developed via a Lewis acid catalyzed tandem acylation-Nazarov cyclization reaction to construct the tricyclic skeleton, followed by installation of the isopropyl group through a strategy involving coumarin formation and its subsequent hydrolysis.

  DOI：

  10.1021/jo500931e

文献信息

• A Very Efficient Route toward the 4a-Methyltetrahydrofluorene Skeleton: Short Synthesis of (±)-Dichroanone and (±)-Taiwaniaquinone H
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Eduardo Cabrera、Esteban Alvarez、Ramón Alvarez-Manzaneda、Ricardo Meneses、Hakima Es-Samti、Antonio Fernández

  DOI：10.1021/jo900153y

  日期：2009.5.1

  A very expedient and efficient new route toward taiwaniaquinoids, bearing the 4a-methyltetrahydrofluorene skeleton, is reported. Key steps are the intramolecular Friedel−Crafts alkylation of an aryldiene and the degradative oxidation of a methylenedioxy group; the latter process could also be utilized for building the 2-hydroxy-1,4-benzoquinone unit, which is frequently found in natural products. Utilizing

  据报道，一条带有4a-甲基四氢芴骨架的，非常有效和有效的新途径通往台湾喹啉类化合物。关键步骤是芳基二烯的分子内Friedel-Crafts烷基化和亚甲基二氧基的降解氧化。后一种方法也可用于构建天然产物中常见的2-羟基-1,4-苯醌单元。利用这种新方法，已经从商业α-（11a）合成了（±）-二氢呋喃酮（7）（三步，总收率77％）和（±）-taiwaniaquinone H（6）（四步，总收率70％）。）或β-cyclocitral（11b）。
• Synthesis of 5-<i>epi</i>-Taiwaniaquinone G
  作者：Jinqian Wang、Jing Wang、Changwei Li、Yonggang Meng、Jie Wu、Chuanjun Song、Junbiao Chang

  DOI：10.1021/jo500931e

  日期：2014.7.3

  A concise synthetic approach to the unnatural 5-epi-taiwaniaquinone G has been developed via a Lewis acid catalyzed tandem acylation-Nazarov cyclization reaction to construct the tricyclic skeleton, followed by installation of the isopropyl group through a strategy involving coumarin formation and its subsequent hydrolysis.