methyl 3-(4-formylphenoxy)-4-benzyloxybenzoate | 220429-85-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3-(4-formylphenoxy)-4-benzyloxybenzoate
• 英文别名: Methyl 3-(4-formylphenoxy)-4-phenylmethoxybenzoate
• CAS: 220429-85-6
• 化学式: C₂₂H₁₈O₅
• 分子量: 362.382
• InChiKey: KIPMSHRZHOQKBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-formylphenoxy)-4-benzyloxybenzoate 在 platinum(IV) oxide lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 四溴化碳 、 氢气 、 六甲基二锡 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 40.0h， 生成 19-Methoxy-4,12-bis(methoxymethoxy)-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
  参考文献：
  名称：

  Total Syntheses of Plagiochins A and D, Macrocyclic Bis(bibenzyls), by Pd(0) Catalyzed Intramolecular Stille-Kelly Reaction1

  摘要：

  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.

  DOI：

  10.3987/com-00-s(i)26
• 作为产物：
  描述：

  4-(苄氧基)-3-羟基苯甲酸甲酯 、 对溴苯甲醛 在 potassium carbonate 、 copper(II) oxide 作用下， 以 吡啶 为溶剂， 反应 48.0h， 以81%的产率得到methyl 3-(4-formylphenoxy)-4-benzyloxybenzoate
  参考文献：
  名称：

  Total Syntheses of Plagiochins A and D, Macrocyclic Bis(bibenzyls), by Pd(0) Catalyzed Intramolecular Stille-Kelly Reaction1

  摘要：

  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.

  DOI：

  10.3987/com-00-s(i)26

文献信息

• Total synthesis of Plagiochin D, a macrocyclic bis(bibenzyl) from liverworts by intramolecular Still-Kelly reaction
  作者：Yoshiyasu Fukuyama、Hideyuki Yaso、Kazuhiko Nakamura、Mitsuaki Kodama

  DOI：10.1016/s0040-4039(98)80031-2

  日期：1999.1

  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.
• 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.