isoplagiochin C | 872607-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: isoplagiochin C
• 英文别名: (20Z)-pentacyclo[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-5,13,16,24-tetrol
• CAS: 872607-47-1
• 化学式: C₂₈H₂₂O₄
• 分子量: 422.48
• InChiKey: AANIEYOTXCALEB-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isoplagiochin C 在 chloroperoxidase from Caldariomyces fumago 、 potassium chloride 、 双氧水 作用下， 生成 Bazzanin Q
  参考文献：
  名称：

  首次在苔藓植物中检测到氯过氧化物酶

  摘要：

  isoplagiochin 类型的氯化环状双苄基是第一个经过验证的来自苔藓植物的卤代代谢物。它们可以通过异普拉乔钦 C 与来自 Caldariomyces fumago 的氯过氧化物酶进行体外氯化获得。此外，第一次在苔藓植物中检测到这种类型的酶，即使用单氯二甲酮测定法在三叶草 Bazzania trilobata 中检测到。

  DOI：

  10.1016/s0031-9422(02)00624-6
• 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 、 三溴化硼 、 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 58.0h， 生成 isoplagiochin C
  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

• Isoplagiochins C and D, New Type of Macrocyclic Bis(bibenzyls), Having Two Biphenyl Linkages from the Liverwort<i>Plagiochila fruticosa</i>
  作者：Toshihiro Hashimoto、Shigeru Kanayama、Yukiko Kan、Motoo Tori、Yoshinori Asakawa

  DOI：10.1246/cl.1996.741

  日期：1996.9

  Two new type of macrocyclic bis(bibenzyls) named isoplagiochins C (1) and D (2) have been isolated from the liverwort Plagiochila fruticosa, and their structures established by a combination of two dimension NMR spectra and chemical degradation.

  从地钱（Plagiochila fruticosa）中分离出两种新型大环双（联苄基）化合物，分别命名为异地钱素C（1）和地钱素D（2），并通过二维核磁共振光谱和化学降解确定了其结构。
• 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.
• Optically active bisbibenzyls from Bazzania trilobata: isolation and stereochemical analysis by chromatographic, chiroptical, and computational methods
  作者：Jochen M. Scher、Josef Zapp、Hans Becker、Nicole Kather、Jürgen Kolz、Andreas Speicher、Michael Dreyer、Katja Maksimenka、Gerhard Bringmann

  DOI：10.1016/j.tet.2004.08.037

  日期：2004.10

  Bazzanin S, a new chlorinated bisbibenzyl of the isoplagiochin D type, as well as isoplagiochin D itself were isolated from the liverwort Bazzania trilobata. The structure of bazzanin S was elucidated based on extensive NMR spectral evidence and by mass spectrometry. Both macrocyclic compounds, bazzanin S and isoplagiochin D, as well as previously reported bazzanins exhibit optical activity, but are not enantiopure in nature. The enantiomeric ratios of a broad array of different cyclic bisbibenzyls, isoplagiochin D, bazzanins A-C and F-J, and bazzanin S, were determined by HPLC on a chiral phase. Exemplarily for the halogen-free parent compound isoplagiochin D, elucidation of the absolute configuration was achieved by quantum chemical CD calculations. (C) 2004 Elsevier Ltd. All rights reserved.
• Syntheses of Cyclic Bisbibenzyl Systems
  作者：Theophil Eicher、Sabine Fey、Werner Puhl、Edwin Büchel、Andreas Speicher

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

  日期：1998.5
• First detection of a chloroperoxidase in bryophytes
  作者：Andreas Speicher、Ronny Heisel、Jürgen Kolz

  DOI：10.1016/s0031-9422(02)00624-6

  日期：2003.3

  Chlorinated cyclic bisbibenzyls of the isoplagiochin type are the first verified halometabolites from bryophytes. They could be obtained by in vitro chlorination of isoplagiochin C with chloroperoxidase from Caldariomyces fumago. Furthermore, an enzyme of this type was detected for the first time in bryophytes namely in the liverwort Bazzania trilobata using the monochlorodimedon assay.

  isoplagiochin 类型的氯化环状双苄基是第一个经过验证的来自苔藓植物的卤代代谢物。它们可以通过异普拉乔钦 C 与来自 Caldariomyces fumago 的氯过氧化物酶进行体外氯化获得。此外，第一次在苔藓植物中检测到这种类型的酶，即使用单氯二甲酮测定法在三叶草 Bazzania trilobata 中检测到。