3-bromo-5-hydroxy-2-methoxybenzaldehyde | 147067-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-bromo-5-hydroxy-2-methoxybenzaldehyde
• CAS: 147067-68-3
• 化学式: C₈H₇BrO₃
• 分子量: 231.046
• InChiKey: YTTGGHQKQUEKGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-5-hydroxy-2-methoxybenzaldehyde 在 吗啉 、 咪唑 、 N,N-二甲基丙烯基脲 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 四丁基氟化铵 、 碘 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 1,2-二溴乙烷 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 二乙二醇二甲醚 、 异丙醇 、 乙腈 为溶剂， 反应 64.75h， 生成 benzoic acid 3-(5-(benzyloxy)-3-{5-(benzoyloxy)-3-[5-(benzyloxy)-3-(bromomethyl)-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 sodium methylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 19.25h， 生成 3-bromo-5-hydroxy-2-methoxybenzaldehyde
  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

• AROMATIC OLIGOMERIC COMPOUNDS USEFUL AS MIMICS OF BIOACTIVE MACROMOLECULES
  申请人：RHONE-POULENC RORER INTERNATIONAL (HOLDINGS) INC.

  公开号：EP0585371A1

  公开（公告）日：1994-03-09
• EP0585371A4
  申请人：——

  公开号：EP0585371A4

  公开（公告）日：1994-07-13
• COMPOSITE MATERIALS COMPRISING MECHANICAL LIGANDS
  申请人：Nanocore Aps

  公开号：EP3737711A1

  公开（公告）日：2020-11-18
• [EN] AROMATIC OLIGOMERIC COMPOUNDS USEFUL AS MIMICS OF BIOACTIVE MACROMOLECULES
  申请人：RHONE-POULENC RORER INTERNATIONAL (HOLDINGS) INC.

  公开号：WO1992020350A1

  公开（公告）日：1992-11-26

  (EN) This invention relates to aromatic oligomeric compounds useful in the treatment of cardiovascular, bone metabolic, hypolipidaemic, neuronal, gastrointestinal and elastase-mediated connective tissue degradation disorders and disorders which may be treated by agents effective in binding DNA, or abnormal smooth muscle cell proliferation, to processes for preparation of such oligomeric compounds, to pharmaceutical compositions including such oligomeric compounds, and their use in the treatment of such disorders.(FR) L'invention concerne des composés oligomères aromatiques utiles dans le traitement de troubles cardio-vasculaires, métaboliques osseux, hypolipidémiques, neuronaux, gastrointestinaux et de dégradation des tissus connectifs induite par élastase ainsi que des troubles qui peuvent être traités par des agents efficaces dans la liaison d'ADN, ou une prolifération anormale des cellules des muscles lisses, l'invention concernant également des procédés de préparation de ces composés oligomères, des compositions pharmaceutiques contenant ces composés oligomères ainsi que leur utilisation dans le traitement de tels troubles.
• 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.