isoplagiochin C tetramethyl ether | 208399-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: isoplagiochin C tetramethyl ether
• 英文别名: (20Z)-5,13,16,24-tetramethoxypentacyclo[20.2.2.110,14.115,19.02,7]octacosa-1(24),2(7),3,5,10(28),11,13,15,17,19(27),20,22,25-tridecaene
• CAS: 208399-80-8
• 化学式: C₃₂H₃₀O₄
• 分子量: 478.588
• InChiKey: WWTMARWRDDCMNE-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isoplagiochin C tetramethyl ether 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以91%的产率得到Isoplagiochin D Tetramethyl Ether
  参考文献：
  名称：

  Syntheses of Cyclic Bisbibenzyl Systems

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<877::aid-ejoc877>3.0.co;2-s
• 作为产物：
  描述：

  2'-[2-(5'-[1,3]Dioxan-2-yl-6,2'-dimethoxy-biphenyl-3-yl)-ethyl]-2,4'-dimethoxy-biphenyl-4-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 、 sodium methylate 、 三溴化磷 、 氯化铵 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 isoplagiochin C tetramethyl ether
  参考文献：
  名称：

  Syntheses of Cyclic Bisbibenzyl Systems

  摘要：

  DOI：

  10.1002/(sici)1099-0690(199805)1998:5<877::aid-ejoc877>3.0.co;2-s

文献信息

• Ring strain and total syntheses of modified macrocycles of the isoplagiochin type
  作者：Andreas Speicher、Timo Backes、Kerstin Hesidens、Jürgen Kolz

  DOI：10.3762/bjoc.5.71

  日期：——

  Macrocycles of the bisbibenzyl-type are natural products that are found exclusively in bryophytes (liverworts). The molecular framework of the subtype “isoplagiochin” is of substantial structural interest because of the chirality of the entire molecule, which arises from two biaryl axes in combination with two helical two-carbon units in a cyclic arrangement. From a structural as well as a synthetic point of view we report on the total synthesis of compounds which possess more rigid two-carbon biaryl bridges like stilbene (E or Z) or even tolane moieties which were introduced starting with a Sonogashira protocol. The McMurry method proved to be a powerful tool for the cyclization to these considerably ring-strained macrocycles.

  双苯基苯并型大环化合物是一类仅在苔藓植物（地钱藓）中发现的天然产物。亚型“异悬叶素”的分子框架具有重要的结构意义，因为整个分子的手性是由两个联合的联苯轴和两个螺旋的双碳单元在循环排列中产生的。从结构和合成的角度来看，我们报道了具有更刚性的双碳联苯桥的化合物的全合成，如苯乙烯（E或Z）或甚至是通过Sonogashira协议引入的甲苯基团。 McMurry方法被证明是将这些具有相当环张力的大环化合物环化的强大工具。
• Syntheses of macrocyclic bisbibenzyls on solid support
  作者：Andreas Speicher、Timo Backes、Stefan Grosse

  DOI：10.1016/j.tet.2005.09.048

  日期：2005.12

  We describe a route for the polymer supported total synthesis of the cyclic bisbibenzyls of the isoplagiochin type found in liverworts. TentaGel (R) resins were used as solid support for a sequence involving Suzuki, Wittig and hydrogenation protocols. The polymer linked intermediates could be characterized by HR-MAS NMR. This route is to be extended to the synthesis of small libraries of differently halogenated derivatives. (c) 2005 Elsevier Ltd. All rights reserved.