(5-Benzyloxy-3-bromo-2-methoxy-benzyloxy)-tert-butyl-diphenyl-silane | 147067-71-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5-Benzyloxy-3-bromo-2-methoxy-benzyloxy)-tert-butyl-diphenyl-silane
• 英文别名: (3-Bromo-2-methoxy-5-phenylmethoxyphenyl)methoxy-tert-butyl-diphenylsilane
• CAS: 147067-71-8
• 化学式: C₃₁H₃₃BrO₃Si
• 分子量: 561.591
• InChiKey: VVZKPHIXBIOYCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-Benzyloxy-3-bromo-2-methoxy-benzyloxy)-tert-butyl-diphenyl-silane 在 吗啉 、 N,N-二甲基丙烯基脲 、 四(三苯基膦)钯 、 四丁基氟化铵 、 碘 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 60.25h， 生成 benzoic acid 3-(5-(benzyloxy)-3-{5-(benzoyloxy)-3-[5-(benzyloxy)-3-(hydroxymethyl)-2-methoxybenzyl]-2-methoxybenzyl}-2-methoxybenzyl)-4-[(2-methoxyethoxy)methoxy]phenyl ester
  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 tetrahydroborate 、 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二乙二醇二甲醚 、 乙腈 为溶剂， 反应 23.75h， 生成 (5-Benzyloxy-3-bromo-2-methoxy-benzyloxy)-tert-butyl-diphenyl-silane
  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

文献信息

• Synthesis of Functionalized Aromatic Oligomers from a Versatile Diphenylmethane Template
  作者：J. G. Bruno、M. N. Chang、Y. M. Choi-Sledeski、D. M. Green、D. G. McGarry、J. R. Regan、F. A. Volz

  DOI：10.1021/jo970596h

  日期：1997.7.1

  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.