1-n-butyl-2,6-dimethoxybenzene | 16929-66-1

• 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: 1-n-butyl-2,6-dimethoxybenzene
• 英文别名: 1,3-dimethoxy-2-butylbenzene；2-butyl-1,3-dimethoxybenzene；2-n-Butyl-1,3-dimethoxybenzene；2-Butyl-resorcin-dimethylaether；Benzene, 1,3-dimethoxy-2-butyl
• CAS: 16929-66-1
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: HKRXKZXKXUTCQU-UHFFFAOYSA-N

物化性质

• 沸点：
  116 °C(Press: 15 Torr)
• 密度：
  0.955±0.06 g/cm3(Predicted)
• 保留指数：
  1422

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-n-butyl-2,6-dimethoxybenzene 在 吡啶盐酸盐 作用下， 反应 8.0h， 生成 2-butylresorcinol
  参考文献：
  名称：

  Synthetic and Structure/Activity Studies on Acid-Substituted 2-Arylphenols: Discovery of 2-[2-Propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]- propoxy]phenoxy]benzoic Acid, a High-Affinity Leukotriene B4 Receptor Antagonist

  摘要：

  Structural derivatives of LY255283 have been studied as receptor antagonists of leukotriene B-4. Substitution of the 2-hydroxyacetophenone subunit of 1 (LY255283) with a 2-arylphenol group provided entry into several new series that feature various mono- and diacidic core functionality. These new analogues, the subject of a broad structure-activity investigation, displayed significantly increased in vitro and in vivo activity as receptor antagonists of LTB(4). A series of diaryl ether carboxylic acids demonstrated especially interesting activity and led to the discovery of compound 43b, 2-[2-propyl-3-[3-[2-ethyl-4-(4-fluorophenyl)-5-hydroxyphenoxy]- propoxy]phenoxy]benzoic acid (LY293111), a 2-arylphenol-substituted diaryl ether carboxylic acid which displayed potent binding to human neutrophils (IC50 = 17 +/- 14.6 nM) and guinea pig lung membranes (IC50 6.6 +/- 0.71 nM), inhibition of LTB(4)-induced expression of the CD11b/CD18 receptor on human neutrophils (IC50 - 3.3 +/- 0.81 nM), and inhibition of LTB(4)-induced contraction of guinea pig lung parenchyma (pK(B) = 8.7 +/- 0.16). In vivo, 43b demonstrated potent activity in inhibiting LTB(4)-induced airway obstruction in the guinea pig when dosed by the oral (ED(50) = 0.40 mg/kg) or intravenous (ED(50) = 0.014 mg/kg) routes. A specific LTB(4) receptor antagonist, 43b had little effect on inhibiting contractions of guinea pig lung parenchyma induced by leukotriene D-4 (LTD(4)), histamine, carbachol, or U46619. Compound 43b has been chosen as a clinical candidate and is currently in phase I studies for a variety of inflammatory diseases.

  DOI：

  10.1021/jm00022a006
• 作为产物：
  描述：

  2-((E)-But-2-enyl)-1,3-dimethoxy-benzene 生成 1-n-butyl-2,6-dimethoxybenzene
  参考文献：
  名称：

  Boltze,K.-H. et al., Justus Liebigs Annalen der Chemie, 1967, vol. 709, p. 63 - 69

  摘要：

  DOI：

文献信息

• Substituted phenyl phenol leukotriene antagonists
  申请人：Eli Lilly and Company

  公开号：US05462954A1

  公开（公告）日：1995-10-31

  Antagonists having a substituted phenyl phenol or a substituted phenolic biphenyl structure, and various derivatives thereof, are specific leukotriene antagonists. Their structures, use and synthesis are disclosed. Also, pharmaceutical formulations are disclosed for use in applications treating diseases or conditions characterized by excessive release of leukotriene B.sub.4, one of the metabolites of arachidonic acid. The primary LTB.sub.4 antagonistic structures are represented as: ##STR1##

  具有取代苯酚或取代酚联苯结构以及各种衍生物的拮抗剂是特定的白三烯拮抗剂。它们的结构、用途和合成已被披露。此外，还公开了用于治疗由花生四烯酸代谢物之一白三烯B.sub.4过度释放所特征的疾病或症状的药物配方。主要的LTB.sub.4拮抗结构表示为：##STR1##
• Leukotriene antagonists for use in the treatment or prevention of alzheimer's disease
  申请人：ELI LILLY AND COMPANY

  公开号：EP0743064A1

  公开（公告）日：1996-11-20

  This invention provides methods for the treatment or prevention of Alzheimer's disease which comprises administering to a mammal in need thereof an effective amount of a compound having activity as a leukotriene antagonist.

  这项发明提供了治疗或预防阿尔茨海默病的方法，包括向需要的哺乳动物施用具有白三烯拮抗活性的化合物的有效量。
• Metalation in hydrocarbon solvents: the mechanistic aspects of substrate-promoted ortho-metalations
  作者：D.W Slocum、Seth Dumbris、Scott Brown、Gina Jackson、Roslyn LaMastus、Elwood Mullins、Jonathan Ray、Phillip Shelton、Amy Walstrom、J Micah Wilcox、R.W Holman

  DOI：10.1016/j.tet.2003.07.010

  日期：2003.10

  The methoxy-substituted aromatic reagents 1,2- and 1,3-dimethoxybenzene (1,2-DMB and 1,3-DMB) and 1,2,4-trimethoxybenzene (1,2,4-TMB) each undergo directed ortho-metalation in high yield in n-BuLi/hydrocarbon media without the aid of a catalyst. These reactions, coined ‘substrate-promoted ortho-metalations’, proceed with the methoxy aromatic substrate functioning as both the directing metalation group

  甲氧基取代的芳族试剂1,2-和1,3-二甲氧基苯（1,2-DMB和1,3-DMB）和1,2,4-三甲氧基苯（1,2,4-TMB）均进行定向邻位无需催化剂即可在正丁基锂/烃介质中高产率地金属化。这些反应称为“底物促进的邻位金属化”，其甲氧基芳族底物既起着直接金属化基团（DMG）的作用，又起着低聚试剂的作用。底物本身用于使n -BuLi脱聚的证据来自131 H NMR。对于三种芳族化合物中的每一种，作为时间的函数形成的金属化产物的相对程度与底物的时间依赖性配位到n -BuLi的能力直接相关，如13 C NMR所测量的。涉及1,2,4-TMB的实验对NMR结果的解释与通过活化的络合物[（1,2,4-TMB）2 ·（n -BuLi）2 ]进行的金属化反应是一致的。最后，从溶解度实验得出的结论是，对于所研究的每种底物促进的金属化，都会在烃溶剂中形成沉淀，并且该沉淀主要包含邻位锂化的芳基中间体。
• Methods for identifying and treating resistant tumors
  申请人：Eli Lilly and Company

  公开号：US06235785B1

  公开（公告）日：2001-05-22

  This invention provides a method of identifying and reversing multidrug resistance in a multidrug resistance tumor comprising administering a multidrug resistance reversing amount of any of the compounds as defined herein.

  该发明提供了一种识别和逆转多药耐药的方法，包括向多药耐药肿瘤中施用本文定义的任何化合物的多药耐药逆转量。
• Method for treating resistant tumors
  申请人：Eli Lilly and Company

  公开号：US05543428A1

  公开（公告）日：1996-08-06

  This invention provides a method of reversing multidrug resistance in a multidrug resistance tumor comprising administering a multidrug resistance reversing amount of any of a series of phenoxy compounds as defined herein.

  这项发明提供了一种逆转多药耐药性的方法，包括向多药耐药性肿瘤施用本文定义的一系列苯氧化合物中的任何一种的多药耐药性逆转剂量。