5-(benzyloxy)-2-methoxy-3-{2-[(2-methoxyethoxy)methoxy]-5-(benzoyloxy)benzyl}benzoic acid | 192698-53-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 5-(benzyloxy)-2-methoxy-3-{2-[(2-methoxyethoxy)methoxy]-5-(benzoyloxy)benzyl}benzoic acid
• CAS: 192698-53-6
• 化学式: C₃₃H₃₂O₉
• 分子量: 572.612
• InChiKey: NWTKSFJTDUVXDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.78
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  109.75
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  L-亮氨酸甲酯盐酸盐 、 5-(benzyloxy)-2-methoxy-3-{2-[(2-methoxyethoxy)methoxy]-5-(benzoyloxy)benzyl}benzoic acid 在 N-甲基吗啉 、 氯甲酸异丙酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以96%的产率得到[4-(2-methoxyethoxymethoxy)-3-[[2-methoxy-3-[[(2S)-1-methoxy-4-methyl-1-oxopentan-2-yl]carbamoyl]-5-phenylmethoxyphenyl]methyl]phenyl] benzoate
  参考文献：
  名称：

  Synthesis of Functionalized Aromatic Oligomers from a Versatile Diphenylmethane Template

  摘要：

  An efficient synthesis of the functionalized diphenylmethane system 1 is described. Selective unmasking of the latent phenol groups on 1 allowed the introduction of various appendages onto the diphenylmethane scaffold via simple alkylation, Mitsunobu etherification, and transition-metal-mediated C-C bond formation. Conversion of 1 to iodide 18 and benzylic zinc reagent 28 followed by palladium(0)-mediated coupling of these derivatives provided homologue 29. Repetitive application of this homologation protocol was used to prepare oligomers of chain length up to 16. Several examples of functional group manipulations on these higher order oligomers are presented. Diphenylmethane 1 was also employed as a key building block in the synthesis of the elastase inhibitor 67. The potential application of extended aromatic oligomers to the field of drug discovery is discussed.

  DOI：

  10.1021/jo970596h
• 作为产物：
  描述：

  benzoic acid 3-bromo-5-formyl-4-hydroxyphenyl ester 在 咪唑 、 sodium chlorite 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 、 四(三苯基膦)钯 、 2-甲基-2-丁烯 、 草酰氯 、 四丁基氟化铵 、 sodium methylate 、 potassium carbonate 、 溶剂黄146 、 1,2-二溴乙烷 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二乙二醇二甲醚 、 二甲基亚砜 、 乙腈 、 叔丁醇 为溶剂， 反应 46.75h， 生成 5-(benzyloxy)-2-methoxy-3-{2-[(2-methoxyethoxy)methoxy]-5-(benzoyloxy)benzyl}benzoic acid
  参考文献：
  名称：

  Synthesis of Functionalized Aromatic Oligomers from a Versatile Diphenylmethane Template

  摘要：

  An efficient synthesis of the functionalized diphenylmethane system 1 is described. Selective unmasking of the latent phenol groups on 1 allowed the introduction of various appendages onto the diphenylmethane scaffold via simple alkylation, Mitsunobu etherification, and transition-metal-mediated C-C bond formation. Conversion of 1 to iodide 18 and benzylic zinc reagent 28 followed by palladium(0)-mediated coupling of these derivatives provided homologue 29. Repetitive application of this homologation protocol was used to prepare oligomers of chain length up to 16. Several examples of functional group manipulations on these higher order oligomers are presented. Diphenylmethane 1 was also employed as a key building block in the synthesis of the elastase inhibitor 67. The potential application of extended aromatic oligomers to the field of drug discovery is discussed.

  DOI：

  10.1021/jo970596h