plagiochin D | 112923-44-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: plagiochin D
• 英文别名: Ppohvzsuyivhkl-uhfffaoysa-；19-methoxy-2-oxapentacyclo[22.2.2.13,7.010,15.016,21]nonacosa-1(26),3,5,7(29),10(15),11,13,16(21),17,19,24,27-dodecaene-4,12-diol
• CAS: 112923-44-1
• 化学式: C₂₉H₂₆O₄
• 分子量: 438.523
• InChiKey: PPOHVZSUYIVHKL-UHFFFAOYSA-N

物化性质

• 沸点：
  645.1±55.0 °C(Predicted)
• 密度：
  1.212±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-5-甲氧基苯甲醛 在 platinum(IV) oxide 、 四(三苯基膦)钯 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 四溴化碳 、 氢溴酸 、 氢气 、 六甲基二锡 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 生成 plagiochin D
  参考文献：
  名称：

  Total synthesis of Plagiochin D, a macrocyclic bis(bibenzyl) from liverworts by intramolecular Still-Kelly reaction

  摘要：

  Plagiochin D (4), a unique macrocyclic bis(bibenzyl) having both a biphenyl ether and a biaryl units isolated from the liverwort Plagiochila acanthophylla, was synthesized. The key 16-membered ring closure of a dibromoperrottetin A derivative 13 was realized by Pd(0) catalyzed intramolecular Still-Kelly reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)80031-2

文献信息

• Total Synthesis of Plagiochin D by an Intramolecular SNAr Reaction
  作者：Julio Cesar Cortes Morales、Alejandro Guillen Torres、Eduardo González-Zamora

  DOI：10.1002/ejoc.201001412

  日期：2011.6

  The total synthesis of plagiochin D, a macrocyclic bis(bibenzyl) compound isolated from the liverwort plagiochila acanthophylla, has been accomplished. Closure of the key 16-membered ring, which contained biphenyl ether and biaryl units, was achieved in good yield by an intramolecular SNAr reaction. The Suzuki and Wittig protocols proved to be powerful tools for the construction of a linear precursor

  plagiochin D 是一种大环双（联苄基）化合物，它是从地草 plagiochila acanthophylla 中分离出来的，已完成全合成。通过分子内 SNAr 反应以良好的收率实现了包含联苯醚和联芳基单元的关键 16 元环的闭合。Suzuki 和 Wittig 方案被证明是构建线性前体的有力工具，该前体对环环化至关重要。
• Total Syntheses of Plagiochins A and D, Macrocyclic Bis(bibenzyls), by Pd(0) Catalyzed Intramolecular Stille-Kelly Reaction1
  作者：Yoshiyasu Fukuyama、Hideyuki Yaso、Takashi Mori、Hironobu Takahashi、Hiroyuki Minami、Mitsuaki Kodama

  DOI：10.3987/com-00-s(i)26

  日期：——

  Total syntheses of plagiochins A (1) and D (4), the former of which exhibits a significant neurotrophic activity, have been accomplished. The key 16-membered ring closure in 4 has been achieved directly from the dibromoperrottetin derivative (7) by Pd(0) catalyzed intramolecular Stille-Kelly reaction, whereas 1 has been synthesized from the dibromide (28) via the trimethylstannyl compounds (29) and (30) by Pd(0) catalyzed intramolecular Stille reaction.
• Total synthesis of plagiochins C and D, macrocyclic bis(bibenzyl) constituents of plagiochila acantophylla
  作者：György M. Keserü、Gabriella Mezey-Vándor、Mihály Nógrádi、Borbála Vermes、Mária Kajtár-Peredy

  DOI：10.1016/s0040-4020(01)88193-x

  日期：——

  Plagiochins C (3) and D (4) were synthesized by convergent schemes. Rings C and B were joined by Ullman ether synthesis, the aryl-aryl bond between rings A and D was formed by Pd(0)-catalysed coupling of an arylboronic acid (ring D) and a bromobenzoic ester (ring A). Ring C and D were linked by the Wittig reaction, while final ring closure was effected by tetraphenylethene assisted Wurtz reaction.