1-methoxy-2-methyl-3-(phenylmethoxy)benzene | 124317-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-methoxy-2-methyl-3-(phenylmethoxy)benzene
• 英文别名: 1-Methoxy-2-methyl-3-phenylmethoxybenzene
• CAS: 124317-22-2
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: WKMPQFBTKWCMPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-methoxy-2-methyl-3-(phenylmethoxy)benzene 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-(3-Methoxy-2-methyl-phenoxy)-propionic acid ethyl ester
  参考文献：
  名称：

  Potential antisecretory antidiarrheals. 2. .alpha.2-Adrenergic 2-[(aryloxy)alkyl]imidazolines

  摘要：

  Lofexidine, an alpha 2-agonist, has central hypotensive activity and peripheral intestinal antisecretory activity. Analogues were synthesized with increased polarity in an attempt to prevent penetration of the blood-brain barrier. The compounds were evaluated in the cholera toxin treated ligated jejunum of the rat and in the Ussing chamber with a rabbit ileum preparation. Active compounds were determined to be alpha 2-adrenergic agonists by yohimbine reversals of their Ussing chamber activities. The 2,6-dimethyl derivative of lofexidine, 4a, was as active as lofexidine in vivo, but derivatives with 2,6-substituents larger than ethyl were inactive. (Aryloxy)alkyl derivatives which have an imidazoline and a methyl or larger group as part of the alkyl exhibited the best antisecretory activity. Compounds with substituents in the para position of the phenyl ring were generally inactive. 3-Amino-2,6-dimethyl derivative 21 was twice as active as 4a. A 2-methyl substituent is required in the 3-amino series to retain good activity. 2-Methyl derivative 12a had activity comparable to that of 4a, while 6-methyl derivative 12f was inactive. Substituents on the 3-amino group did not affect the activity, but substituting a hydroxyl for the amino group produced an inactive compound. Replacing the phenyl moiety with a 4-indole resulted in retention of activity, but other heterocycles were inactive. Compound 12a was resolved and d isomer 32 was five times more potent than l isomer 33. The more active compounds in the rat cholera toxin assay (RCTA), when evaluated in the dog, exhibited antisecretory activity but also exhibited central nervous system (CNS) effects, sedation and ataxia, at 10 mg/kg, and in spontaneously hypertensive rats at 50 mg/kg. A measure of polarity, log P, was calculated for the (aryloxy)alkyl groups. Regression analysis showed no correlation of antisecretory ED50 to the calculated log P. The active compounds did not show a separation of the central CNS effects from the peripheral antisecretory activity by increasing the polarity.

  DOI：

  10.1021/jm00164a024
• 作为产物：
  描述：

  2,6-二羟基甲苯 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 1-methoxy-2-methyl-3-(phenylmethoxy)benzene
  参考文献：
  名称：

  Potential antisecretory antidiarrheals. 2. .alpha.2-Adrenergic 2-[(aryloxy)alkyl]imidazolines

  摘要：

  Lofexidine, an alpha 2-agonist, has central hypotensive activity and peripheral intestinal antisecretory activity. Analogues were synthesized with increased polarity in an attempt to prevent penetration of the blood-brain barrier. The compounds were evaluated in the cholera toxin treated ligated jejunum of the rat and in the Ussing chamber with a rabbit ileum preparation. Active compounds were determined to be alpha 2-adrenergic agonists by yohimbine reversals of their Ussing chamber activities. The 2,6-dimethyl derivative of lofexidine, 4a, was as active as lofexidine in vivo, but derivatives with 2,6-substituents larger than ethyl were inactive. (Aryloxy)alkyl derivatives which have an imidazoline and a methyl or larger group as part of the alkyl exhibited the best antisecretory activity. Compounds with substituents in the para position of the phenyl ring were generally inactive. 3-Amino-2,6-dimethyl derivative 21 was twice as active as 4a. A 2-methyl substituent is required in the 3-amino series to retain good activity. 2-Methyl derivative 12a had activity comparable to that of 4a, while 6-methyl derivative 12f was inactive. Substituents on the 3-amino group did not affect the activity, but substituting a hydroxyl for the amino group produced an inactive compound. Replacing the phenyl moiety with a 4-indole resulted in retention of activity, but other heterocycles were inactive. Compound 12a was resolved and d isomer 32 was five times more potent than l isomer 33. The more active compounds in the rat cholera toxin assay (RCTA), when evaluated in the dog, exhibited antisecretory activity but also exhibited central nervous system (CNS) effects, sedation and ataxia, at 10 mg/kg, and in spontaneously hypertensive rats at 50 mg/kg. A measure of polarity, log P, was calculated for the (aryloxy)alkyl groups. Regression analysis showed no correlation of antisecretory ED50 to the calculated log P. The active compounds did not show a separation of the central CNS effects from the peripheral antisecretory activity by increasing the polarity.

  DOI：

  10.1021/jm00164a024

文献信息

• Pyrimidine Derivatives As HSP90 Inhibitors
  申请人：Chessari Gianni

  公开号：US20090215777A1

  公开（公告）日：2009-08-27

  The invention provides a compound for use as an inhibitor of Hsp90, the compound having the formula (I): or salts, tautomers, solvates or N-oxides thereof; wherein: A is N or a group CR 3 ; R 1 is a monocyclic or bicyclic carbocyclic or heterocyclic ring of 5 to 10 ring members of which up to two ring members may be heteroatoms selected from N, O and S and the remainder are carbon atoms, the carbocyclic or heterocyclic ring being optionally substituted by one or more substituent groups independently selected from R 10 ; and R 2 , R 3 and R 10 are as defined in the claims.

  该发明提供了一种化合物，用作Hsp90的抑制剂，该化合物具有以下式（I）：或其盐、互变异构体、溶剂合物或N-氧化物；其中：A为N或CR基团；R1为由5至10个环成员组成的单环或双环碳环或杂环，其中最多两个环成员可以是从N、O和S中选择的杂原子，其余为碳原子，碳环或杂环可以选择地被一个或多个取代基独立地选择自R10的取代基取代；而R2、R3和R10如权利要求中所定义。
• Regioselective lithiation of aryl benzyl ethers
  作者：Jan Chodakowski、Tomasz Kliś、Janusz Serwatowski

  DOI：10.1016/j.tetlet.2005.02.006

  日期：2005.3

  The lithiation of a series of aryl benzyl ethers containing -F and -OMe groups has been studied. It was found that the presence of one or two fluorine atoms in the meta position relative to the oxygen atom prevents the lithiation at the benzyl carbon atom. 3-(3',5'-Dimethoxybenzyloxy)fluorobenzene was lithiated and next reacted with DMF to give 2-(3',5'-dimethoxybenzyloxy)6-fluorobenzaldehyde. A three-step procedure was applied to remove three hydrogen atoms from l,3-difluoro-5-(3',5'-dimethoxybenzyloxy)benzene and replace them with methyl groups by reactions of the lithiated compounds with MeI. (C) 2005 Elsevier Ltd. All rights reserved.
• A direct alkylation of resorcinols
  作者：Eleana Lopušanskaja、Anne Paju、Ivar Järving、Margus Lopp

  DOI：10.1080/00397911.2023.2214645

  日期：2023.8.3
• RESORCINOLIC DERIVATIVE FOR RUBBER COMPOUNDS
  申请人：INDSPEC CHEMICAL CORPORATION

  公开号：EP1358262A2

  公开（公告）日：2003-11-05
• EP1358262A4
  申请人：——

  公开号：EP1358262A4

  公开（公告）日：2005-01-12