3,5-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-ol
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: OIXORIFAOVBRHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-ol 在 potassium permanganate 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 水 、 三溴化硼 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 50.0h， 生成 4,7,9-trimethoxy-1-(4-methoxyphenyl)-6H-anthra[1,9-bc]furan-6-one
  参考文献：
  名称：

  Total synthesis of penta-Me amurensin H and diptoindonesin G featuring a Rh-catalyzed carboacylation/aromatization cascade enabled by C C activation

  摘要：

  Oligostilbenoids represented a family of natural products, which contained one or several multifused benzofuran substructures and displayed promising biological activities towards cancer as well as immunological therapeutic targets. A convergent-divergent strategy featuring Rh-catalyzed carboacylation/aromatization cascade reaction based on C-C activation of benzocyclbutenones had been conceived. penta-Methyl amurensin H and diptoindolnesin G were successfully synthesized without any protecting groups, constituting a new entry towards oligostilbenoids' natural product synthesis. The synthesis completed within 10 steps for both natural products, suggesting conciseness and efficacy of the C-C activation in complex natural product synthesis. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2019.02.040
• 作为产物：
  描述：

  四氢呋喃 、 1-溴-3,5-二甲氧基苯 在 正丁基锂 、 2,2,6,6-四甲基哌啶 作用下， 以 正己烷 为溶剂， 反应 16.0h， 以82%的产率得到3,5-dimethoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-ol
  参考文献：
  名称：

  Total synthesis of penta-Me amurensin H and diptoindonesin G featuring a Rh-catalyzed carboacylation/aromatization cascade enabled by C C activation

  摘要：

  Oligostilbenoids represented a family of natural products, which contained one or several multifused benzofuran substructures and displayed promising biological activities towards cancer as well as immunological therapeutic targets. A convergent-divergent strategy featuring Rh-catalyzed carboacylation/aromatization cascade reaction based on C-C activation of benzocyclbutenones had been conceived. penta-Methyl amurensin H and diptoindolnesin G were successfully synthesized without any protecting groups, constituting a new entry towards oligostilbenoids' natural product synthesis. The synthesis completed within 10 steps for both natural products, suggesting conciseness and efficacy of the C-C activation in complex natural product synthesis. (C) 2019 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2019.02.040

文献信息

• Synthesis of Oxygenated ortho-Methylbenzaldehydes via Aryne [2+2] Cycloaddition and Benzocyclobutenol Ring Opening
  作者：Mark M. Maturi、Ken Ohmori、Keisuke Suzuki

  DOI：10.2533/chimia.2018.870

  日期：——

  oxygenated ortho-methylbenzaldehyde derivatives, starting from commercially available bromoarenes, is described. The synthesis features the simultaneous and highly regioselective installation of both the methyl and the formyl group onto the benzene core via benzyne [2+2] cycloadditions with acetaldehyde lithium enolate to give the corresponding benzocyclobutenols in high yields. Bond-selective ring opening

  本文描述了从市售溴代芳烃开始制备氧化邻甲基苯甲醛衍生物的两步程序。该合成的特点是通过与乙醛烯醇锂的苯炔[2+2]环加成反应，将甲基和甲酰基同时且高度区域选择性地安装到苯核上，以高产率得到相应的苯并环丁烯醇。苯并环丁烯醇在碱性条件下在甲醇中进行键选择性开环，得到标题化合物。