2,13,20-Tribenzyloxy-15,6,17,18-tetrahydro-3-methoxy-7,10-etheno-12,16-metheno-16H-dibenzoxacyclooctadecin | 139962-91-7

• 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: 2,13,20-Tribenzyloxy-15,6,17,18-tetrahydro-3-methoxy-7,10-etheno-12,16-metheno-16H-dibenzoxacyclooctadecin
• 英文别名: 19-Methoxy-4,12,18-tris(phenylmethoxy)-2-oxapentacyclo[22.2.2.13,7.010,15.016,21]nonacosa-1(26),3,5,7(29),10(15),11,13,16,18,20,24,27-dodecaene
• CAS: 139962-91-7
• 化学式: C₅₀H₄₄O₅
• 分子量: 724.896
• InChiKey: WCQSXUTXDFMPIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  55
• 可旋转键数：
  10
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,13,20-Tribenzyloxy-15,6,17,18-tetrahydro-3-methoxy-7,10-etheno-12,16-metheno-16H-dibenzoxacyclooctadecin 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 Plagiochin C
  参考文献：
  名称：

  Total synthesis of plagiochins C and D, macrocyclic bis(bibenzyl) constituents of plagiochila acantophylla

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)88193-x
• 作为产物：
  描述：

  methyl 4-(benzyloxy)-2-bromo-5-methoxybenzoate 在 palladium on activated charcoal lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 氢气 、 sodium methylate 、 sodium 、 三溴化磷 、 碳酸氢钠 、 potassium carbonate 、 1,1,2,2-四苯乙烯 、 potassium iodide 作用下， 以 甲醇 、 乙醚 、 乙醇 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 反应 11.83h， 生成 2,13,20-Tribenzyloxy-15,6,17,18-tetrahydro-3-methoxy-7,10-etheno-12,16-metheno-16H-dibenzoxacyclooctadecin
  参考文献：
  名称：

  Total synthesis of plagiochins C and D, macrocyclic bis(bibenzyl) constituents of plagiochila acantophylla

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)88193-x

文献信息

• 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.