2-(2,5-二甲氧基苯基)丁烷 | 13620-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(2,5-二甲氧基苯基)丁烷
• 英文名称: 2-(2,5-dimethoxyphenyl)butane
• 英文别名: 1,4-Dimethoxy-2-sec.-butyl-benzol；2-sec-butyl-1,4-dimethoxy-benzene；2-sec-Butyl-1,4-dimethoxy-benzol；2-Butan-2-yl-1,4-dimethoxybenzene
• CAS: 13620-78-5
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: CRPDVUBVRNFSCZ-UHFFFAOYSA-N

物化性质

• 沸点：
  114-115 °C(Press: 4 Torr)
• 密度：
  0.952±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  4
• 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：

  2-(2,5-二甲氧基苯基)丁烷 在 ammonium acetate 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-<2,5-dimethoxy-4-(2-butyl)phenyl>-2-nitropropene
  参考文献：
  名称：

  Substituent branching in phenethylamine-type hallucinogens: a comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane

  摘要：

  Two novel hallucinogen analogues related to 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM, STP) were synthesized and evaluated in the two-lever drug discrimination paradigm by using 0.08 mg/kg of LSD as the training drug stimulus. The two compounds differ from each other only with respect to the point of branching in the 4-alkyl group. However, pharmacological evaluation revealed a clear difference in difference in potency and degree of LSD generalization for the two isomers. Branching adjacent to the ring, as in the 4-(2-butyl) analogue, may provide steric interference to the formation of the drug-receptor complex, while branching one methylene unit removed from the ring, as in the 4-(2-methylpropyl) analogue, poses less of a steric problem for the drug-receptor interaction. This is consistent with the idea that formation of a charge-transfer complex between the hallucinogen molecule and the receptor may be one of the features of this drug-receptor interaction.

  DOI：

  10.1021/jm00372a015
• 作为产物：
  描述：

  2,5-二甲氧基苯乙酮 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 magnesium 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 2.0h， 生成 2-(2,5-二甲氧基苯基)丁烷
  参考文献：
  名称：

  Substituent branching in phenethylamine-type hallucinogens: a comparison of 1-[2,5-dimethoxy-4-(2-butyl)phenyl]-2-aminopropane and 1-[2,5-dimethoxy-4-(2-methylpropyl)phenyl]-2-aminopropane

  摘要：

  Two novel hallucinogen analogues related to 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM, STP) were synthesized and evaluated in the two-lever drug discrimination paradigm by using 0.08 mg/kg of LSD as the training drug stimulus. The two compounds differ from each other only with respect to the point of branching in the 4-alkyl group. However, pharmacological evaluation revealed a clear difference in difference in potency and degree of LSD generalization for the two isomers. Branching adjacent to the ring, as in the 4-(2-butyl) analogue, may provide steric interference to the formation of the drug-receptor complex, while branching one methylene unit removed from the ring, as in the 4-(2-methylpropyl) analogue, poses less of a steric problem for the drug-receptor interaction. This is consistent with the idea that formation of a charge-transfer complex between the hallucinogen molecule and the receptor may be one of the features of this drug-receptor interaction.

  DOI：

  10.1021/jm00372a015

文献信息

• Substituent effects in the oxidation of 2-alkyl-1,4-dialkoxybenzenes with ceric ammonium nitrate
  作者：Brian E. Love、Alexander L. Simmons

  DOI：10.1016/j.tetlet.2016.11.042

  日期：2016.12

  Increased steric size of alkyl groups and the presence of coordinating atoms on alkoxy groups have both been found to contribute to decreasing yields of diquinones upon reaction of 2-alkyl-1,4-dialkoxybenzenes with CAN. The overall hydrophilicity of the substrates does not appear to be a significant factor in determining the diquinone yield for these reactions.

  已经发现，当2-烷基-1，4-二烷氧基苯与CAN反应时，增加的烷基空间尺寸和在烷氧基上存在配位原子均有助于降低二醌的收率。底物的整体亲水性似乎不是决定这些反应的二醌产率的重要因素。
• Modulators of ATP-Binding Cassette Transporters
  申请人：Hadida Ruah Sara S.

  公开号：US20120322798A1

  公开（公告）日：2012-12-20

  Compounds of the present invention, and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTC”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

  本发明的化合物及其药学上可接受的组成物，可用作ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节因子（“CFTC”）。本发明还涉及使用本发明的化合物治疗ABC转运蛋白介导的疾病的方法。
• 502. Alkylation of the aromatic nucleus. Part III. The reaction of phenols with the n-butyl ester of methanesulphonic acid
  作者：M. S. Grant、W. J. Hickinbottom

  DOI：10.1039/jr9590002513

  日期：——
• 2,10-Disubstituted dibenzo(b,d)pyrans and benzo(c)quinolines and pharmaceutical compositions thereof
  申请人：PFIZER INC.

  公开号：EP0009386B1

  公开（公告）日：1982-11-17
• US7956052B2
  申请人：——

  公开号：US7956052B2

  公开（公告）日：2011-06-07