Methyl 5-[(benzyloxy)methyl]-5-[(4-methoxyphenoxy)methyl]tetrahydro-2-furancarboxylate | 367263-50-1

• 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 5-[(benzyloxy)methyl]-5-[(4-methoxyphenoxy)methyl]tetrahydro-2-furancarboxylate
• CAS: 367263-50-1
• 化学式: C₂₃H₂₈O₆
• 分子量: 400.472
• InChiKey: GWRDVTIKYKLSQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Methyl 5-[(benzyloxy)methyl]-5-[(4-methoxyphenoxy)methyl]tetrahydro-2-furancarboxylate 在 palladium on activated charcoal 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 3.5h， 生成 (rel-2S,5R)-Methyl 5-(hydroxymethyl)-5-[(tetradecanoyloxy)methyl]tetrahydro-2-furancarboxylate
  参考文献：
  名称：

  5-Acyloxy-5-hydroxymethyltetrahydro-2-furancarboxylate as a novel template for protein kinase C (PKC) binding

  摘要：

  A series of alkyl tetrahydrofuran-2-carboxylates (1-4) bearing a new set of three pharmacophoric groups were tested as protein kinase C (PKC) ligands. The compounds were synthesized from commercially available glycidyl 4-methoxyphenyl ether. The correlation between their binding affinities for PKC-alpha and a conformational fit to phorbol ester indicates they mimic a pharmacophore model comprising the C-20-OH, C-3-C=O and C-9-OH rather than that including the C-13-C=O moiety. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01077-1
• 作为产物：
  描述：

  5-[(Benzyloxy)methyl]-5-[(4-metoxyphenoxy)methyl]tetrahydro-2-furanol 在 盐酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 17.08h， 生成 Methyl 5-[(benzyloxy)methyl]-5-[(4-methoxyphenoxy)methyl]tetrahydro-2-furancarboxylate
  参考文献：
  名称：

  5-Acyloxy-5-hydroxymethyltetrahydro-2-furancarboxylate as a novel template for protein kinase C (PKC) binding

  摘要：

  A series of alkyl tetrahydrofuran-2-carboxylates (1-4) bearing a new set of three pharmacophoric groups were tested as protein kinase C (PKC) ligands. The compounds were synthesized from commercially available glycidyl 4-methoxyphenyl ether. The correlation between their binding affinities for PKC-alpha and a conformational fit to phorbol ester indicates they mimic a pharmacophore model comprising the C-20-OH, C-3-C=O and C-9-OH rather than that including the C-13-C=O moiety. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01077-1