2-丁基硫烷基-1,4-二甲氧基苯 | 24920-40-9

• 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-丁基硫烷基-1,4-二甲氧基苯
• 英文名称: 1,4-dimethoxy-2-n-butylthiobenzene
• 英文别名: 2-(Butylthio)-1,4-dimethoxybenzol；butyl(2,5-dimethoxyphenyl)sulfane；2-(Butylsulfanyl)-1,4-dimethoxybenzene；2-butylsulfanyl-1,4-dimethoxybenzene
• CAS: 24920-40-9
• 化学式: C₁₂H₁₈O₂S
• 分子量: 226.34
• InChiKey: SYVBNBNOXZNPKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-丁基硫烷基-1,4-二甲氧基苯 在 ammonium acetate 、 三氯氧磷 作用下， 反应 0.25h， 生成 1-(2,5-dimethoxy-4-n-butylthiophenyl)-2-nitro-1-propene
  参考文献：
  名称：

  Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling

  摘要：

  A series of phenethylamine derivatives with various ring substituents and with or without N-methyl and/or C-alpha methyl or ethyl groups was synthesized and assayed for their ability reversibly to inhibit monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds. showed potent and selective MAO-A inhibitory activity (IC50 in the submicromolar range) but none showed appreciable activity toward MAO-B. A three-dimensional quantitative structure-activity relationship study for MAO-A inhibition was performed on the series using comparative molecular field analysis (CoMFA). The resulting model gave a cross-validated q(2) of 0.72 and showed that in this series of compounds steric properties of the substituents were more important than electrostatic effects. Molecular modeling based on the recently published crystal structure of inhibitor-bound MAO-A provided detailed evidence for specific interactions of the ligands with the enzyme, supported by previous references and consistent with results from the CoMFA. On the basis of these results, structural determinants for selectivity of substituted amphetamines for MAO-A are discussed.

  DOI：

  10.1021/jm0493109
• 作为产物：
  描述：

  2,5-二甲氧基苯磺酰氯 在 盐酸 、 氢氧化钾 、 锌 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 2-丁基硫烷基-1,4-二甲氧基苯
  参考文献：
  名称：

  Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling

  摘要：

  A series of phenethylamine derivatives with various ring substituents and with or without N-methyl and/or C-alpha methyl or ethyl groups was synthesized and assayed for their ability reversibly to inhibit monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds. showed potent and selective MAO-A inhibitory activity (IC50 in the submicromolar range) but none showed appreciable activity toward MAO-B. A three-dimensional quantitative structure-activity relationship study for MAO-A inhibition was performed on the series using comparative molecular field analysis (CoMFA). The resulting model gave a cross-validated q(2) of 0.72 and showed that in this series of compounds steric properties of the substituents were more important than electrostatic effects. Molecular modeling based on the recently published crystal structure of inhibitor-bound MAO-A provided detailed evidence for specific interactions of the ligands with the enzyme, supported by previous references and consistent with results from the CoMFA. On the basis of these results, structural determinants for selectivity of substituted amphetamines for MAO-A are discussed.

  DOI：

  10.1021/jm0493109

文献信息

• Synthese von neuen (Phenylalkyl)aminen zur Untersuchung von Struktur–Aktivitätsbeziehungen. Mitteilung 2
  作者：Daniel Trachsel

  DOI：10.1002/hlca.200390210

  日期：2003.7

  Synthesis of Novel (Phenylalkyl)amines for the Investigation of Structure–Activity Relationships. Part 21). 4-Thio-Substituted [2-(2,5-Dimethoxyphenyl)ethyl]amines (=2,5-Dimethoxybenzeneethanamines)

  新型（苯基烷基）胺的合成，用于研究结构与活性之间的关系。第2部分1）。4-硫代取代的[2-（2,5-二甲氧基苯基）乙基]胺（= 2,5-二甲氧基苯乙胺）
• Construction of C−S and C−Se Bonds from Unstrained Ketone Precursors under Photoredox Catalysis
  作者：Hao Wu、Shuguang Chen、Chunni Liu、Quansheng Zhao、Zhen Wang、Qiren Jin、Shijie Sun、Jing Guo、Xinwei He、Patrick J Walsh、Yongjia Shang

  DOI：10.1002/anie.202314790

  日期：2024.2.19

  precursors has been developed to construct sulfides, disulfides, selenides, sulfoxides and sulfones. Combining this deacylative process with SN2 or coupling reactions provides novel and convenient modular approaches toward unsymmetrical or symmetrical disulfides.

  已经开发出一种使用无张力甲基酮作为自由基前体的温和光催化脱酰策略来构建硫化物、二硫化物、硒化物、亚砜和砜。将此脱酰过程与 S N 2 或偶联反应相结合，为不对称或对称二硫化物提供了新颖且方便的模块化方法。
• Kuliev,A.M. et al., Journal of Organic Chemistry USSR (English Translation), 1969, vol. 5, p. 1760 - 1762
  作者：Kuliev,A.M. et al.

  DOI：——

  日期：——
• Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling
  作者：Alejandra Gallardo-Godoy、Angélica Fierro、Thomas H. McLean、Mariano Castillo、Bruce K. Cassels、Miguel Reyes-Parada、David E. Nichols

  DOI：10.1021/jm0493109

  日期：2005.4.1

  A series of phenethylamine derivatives with various ring substituents and with or without N-methyl and/or C-alpha methyl or ethyl groups was synthesized and assayed for their ability reversibly to inhibit monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds. showed potent and selective MAO-A inhibitory activity (IC50 in the submicromolar range) but none showed appreciable activity toward MAO-B. A three-dimensional quantitative structure-activity relationship study for MAO-A inhibition was performed on the series using comparative molecular field analysis (CoMFA). The resulting model gave a cross-validated q(2) of 0.72 and showed that in this series of compounds steric properties of the substituents were more important than electrostatic effects. Molecular modeling based on the recently published crystal structure of inhibitor-bound MAO-A provided detailed evidence for specific interactions of the ligands with the enzyme, supported by previous references and consistent with results from the CoMFA. On the basis of these results, structural determinants for selectivity of substituted amphetamines for MAO-A are discussed.