2,6-difluoroveratraldehyde | 152434-99-6

• 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: 2,6-difluoroveratraldehyde
• 英文别名: 2,6-Difluoro-3,4-dimethoxybenzaldehyde
• CAS: 152434-99-6
• 化学式: C₉H₈F₂O₃
• 分子量: 202.158
• InChiKey: UDOBXTADCGSCLS-UHFFFAOYSA-N

物化性质

• 沸点：
  260.8±35.0 °C(Predicted)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  2,6-difluoroveratraldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 8.0h， 生成 2-(2,6-Difluoro-3,4-dimethoxyphenyl)ethylamine
  参考文献：
  名称：

  Nie, Jun-Ying; Shi, Dan; Daly, John W., Medicinal Chemistry Research, 1996, vol. 6, # 5, p. 318 - 332

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二氟-2-甲氧基苯甲醛 在 咪唑 、 盐酸 、 氢氧化钾 、 仲丁基锂 、 potassium carbonate 、 间氯过氧苯甲酸 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 2.5h， 生成 2,6-difluoroveratraldehyde
  参考文献：
  名称：

  Syntheses of 2,5- and 2,6-difluoronorepinephrine, 2,5-difluoroepinephrine, and 2,6-difluorophenylephrine: effect of disubstitution with fluorine on adrenergic activity

  摘要：

  Synthetic routes to difluorinated analogs of the adrenergic agonists, norepinephrine (NE), epinephrine (E), and phenylephrine (PE) have been developed. The syntheses were based on elaboration of the ethanolamine side chains from the appropriately polyfunctionalized benzaldehydes, The benzaldehydes were prepared from precursor difluorinated benzenes by sequential regioselective lithiations and reaction with electrophiles to introduce hydroxyl and carboxaldehyde functionalities. Binding and functional assay data demonstrate that the 2,6-difluorinated analogs are relatively inactive at both alpha- and beta-adrenergic receptors. These results are consistent with earlier observations that 2-fluoro substitution of adrenergic agonists decreases alpha-adrenergic activity whereas 6-fluoro substitution decreases beta-adrenergic activity.

  DOI：

  10.1021/jm00076a024

文献信息

• [EN] PENICILLIN-BINDING PROTEIN INHIBITORS<br/>[FR] INHIBITEURS DE PROTÉINE DE LIAISON À LA PÉNICILLINE
  申请人：VENATORX PHARMACEUTICALS INC

  公开号：WO2021108023A1

  公开（公告）日：2021-06-03

  Described herein are certain boron-containing compounds, compositions, preparations and their use as modulators of the transpeptidase function of bacterial penicillin-binding proteins and as antibacterial agents. In some embodiments, the compounds described herein inhibit penicillin-binding proteins. In certain embodiments, the compounds described herein are useful in the treatment of bacterial infections.

  本文描述了某些含硼化合物、组合物、制剂及其作为细菌青霉素结合蛋白的跨肽酶功能调节剂和抗菌剂的用途。在某些实施例中，本文描述的化合物抑制青霉素结合蛋白。在某些实施例中，本文描述的化合物在治疗细菌感染方面是有用的。
• Synthesis of 2,6-difluorodopamine and 3-(2,6-difluoro-3,4-dihydroxyphenyl)alanine
  作者：Jung-ying Nie、Kenneth L. Kirk

  DOI：10.1016/0022-1139(95)90109-u

  日期：1995.10

  2,6-Difluorodopamine and 3-(2,6-difluoro-3,4-dihydroxyphenyl)alanine were prepared by side-chain elaboration of 2,6-difluoroveratraldehyde, followed by removal of protecting groups.
• Convenient syntheses of 2-, 5- and 6-fluoro- and 2,6-difluoro-l-DOPA
  作者：Wei-Ping Deng、Kelli A. Wong、KennethL. Kirk

  DOI：10.1016/s0957-4166(02)00321-x

  日期：2002.6

  Alkylation under phase transfer conditions of the chiral glycine synthon 2 (prepared from the commercially available Oppolzer chiral sultam) with fluorinated analogues of 3,4-dimethoxybenzyl chloride proceeded with high diastereoselectivity. Hydrolysis of the Schiff base, removal of the chiral auxiliary and HBr demethylation produced 2-, 5-, 6-fluoro- and 2,6-difluoro-L-DOPA in e.e. of >99%. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of fluoro- and polyfluoro-veratraldehydes by electrophilic fluorination
  作者：Jun-ying Nie、Kenneth L. Kirk

  DOI：10.1016/0022-1139(95)90108-t

  日期：1995.10

  Lithiation of oxazolines derived from fluorinated veratric acid, followed by electrophilic fluorination and subsequent reductive oxazoline cleavage, provides a convenient route to di- and tri-fluoroveratraldehydes. Similarly, 4-fluoroveratrol was converted by lithiation and fluorination to 3,4-difluoroveratrol, which can be used to prepare 5,6-difluoroveratraldehyde.
• Syntheses of 2,5- and 2,6-difluoronorepinephrine, 2,5-difluoroepinephrine, and 2,6-difluorophenylephrine: effect of disubstitution with fluorine on adrenergic activity
  作者：George T. Chen、Michael King、Fabian Gusovsky、Cyrus R. Creveling、John W. Daly、Bang Hua Chen、Jun Ying Nie、Kenneth L. Kirk

  DOI：10.1021/jm00076a024

  日期：1993.11

  Synthetic routes to difluorinated analogs of the adrenergic agonists, norepinephrine (NE), epinephrine (E), and phenylephrine (PE) have been developed. The syntheses were based on elaboration of the ethanolamine side chains from the appropriately polyfunctionalized benzaldehydes, The benzaldehydes were prepared from precursor difluorinated benzenes by sequential regioselective lithiations and reaction with electrophiles to introduce hydroxyl and carboxaldehyde functionalities. Binding and functional assay data demonstrate that the 2,6-difluorinated analogs are relatively inactive at both alpha- and beta-adrenergic receptors. These results are consistent with earlier observations that 2-fluoro substitution of adrenergic agonists decreases alpha-adrenergic activity whereas 6-fluoro substitution decreases beta-adrenergic activity.