2-(5-甲氧基-1-苯并呋喃-3-基)-N,N-二甲基乙胺 | 140853-58-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 2-(5-甲氧基-1-苯并呋喃-3-基)-N,N-二甲基乙胺
• 中文别名: 吡啶,5-(二甲基甲硅烷基)-2-(乙硫基)-(9CI)
• 英文名称: N,N-dimethyl-2-(5-methoxybenzofuran-3-yl)ethanamine
• 英文别名: [2-(5-methoxybenzofuran-3-yl)ethyl]dimethylamine；2-(5-methoxy-1-benzofuran-3-yl)-N,N-dimethylethanamine
• CAS: 140853-58-3
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: WBPQJTBOQCCTFX-UHFFFAOYSA-N

物化性质

• 沸点：
  312.9±32.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  25.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(5-methoxybenzofuran-3-yl)ethanol 在 吡啶 作用下， 以 乙腈 为溶剂， 生成 2-(5-甲氧基-1-苯并呋喃-3-基)-N,N-二甲基乙胺
  参考文献：
  名称：

  Benzofuran bioisosteres of hallucinogenic tryptamines

  摘要：

  The benzofuran analogues of the hallucinogens 5-methoxy-NN-dimethyltryptamine and 5-methoxy-alpha-methyl-tryptamine were synthesized and evaluated for affinity at the serotonin 5-HT2 and 5-HT1A receptors in rat brain homogenate, labeled with [I-125]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane ([I-125]DOI) and [H-3]-8-hydroxy-2-(N,N-di-n-propylamino)tetralin ([H-3]-8-OH-DPAT), respectively. At the 5-HT2 receptor, the benzofurans had slightly decreased affinities, approximately one-third and one-sixth those of the indoles, for the primary amines and the tertiary amines, respectively. The benzofurans also had lower affinity at the 5-HTA1A receptor, but decreased only about 20-30% from that of the indole isosteres. Thus, the 5-HT1A receptor is less discriminating with respect to preference for an indole versus a benzofuran, although all of the compounds did have higher affinities for the 5-HT2 receptor than for the 5-HT1A receptor. It is suggested that benzofurans may be useful in the design of serotonin receptor ligands.

  DOI：

  10.1021/jm00089a017

文献信息

• Brønsted Acid Mediated Cascade Reaction To Access 3-(2-Bromoethyl)benzofurans
  作者：Stefania Porcu、Stefania Demuro、Alberto Luridiana、Andrea Cocco、Angelo Frongia、David J. Aitken、Florence Charnay-Pouget、Regis Guillot、Giorgia Sarais、Francesco Secci

  DOI：10.1021/acs.orglett.8b03429

  日期：2018.12.7

  A unified protocol for the construction of 3-(2-bromoethyl)benzofurans and 2-(benzofuran-3-yl)ethylamines from bis[(trimethylsilyl)oxy]cyclobutene has been developed. This mild and facile strategy was applied for the synthesis of a series of 5-HT serotonin receptor agonists, underlining its potential for the syntheses of bioactive compounds and natural products.

  从双[（三甲基甲硅烷基）氧基]环丁烯构建3-（2-溴乙基）苯并呋喃和2-（苯并呋喃-3-基）乙胺的统一协议已经开发出来。这种温和而简便的策略适用于一系列5-HT血清素受体激动剂的合成，突显了其在合成生物活性化合物和天然产物方面的潜力。
• Benzofuran bioisosteres of hallucinogenic tryptamines
  作者：Zbigniew Tomaszewski、Michael P. Johnson、Xuemei Huang、David E. Nichols

  DOI：10.1021/jm00089a017

  日期：1992.5

  The benzofuran analogues of the hallucinogens 5-methoxy-NN-dimethyltryptamine and 5-methoxy-alpha-methyl-tryptamine were synthesized and evaluated for affinity at the serotonin 5-HT2 and 5-HT1A receptors in rat brain homogenate, labeled with [I-125]-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane ([I-125]DOI) and [H-3]-8-hydroxy-2-(N,N-di-n-propylamino)tetralin ([H-3]-8-OH-DPAT), respectively. At the 5-HT2 receptor, the benzofurans had slightly decreased affinities, approximately one-third and one-sixth those of the indoles, for the primary amines and the tertiary amines, respectively. The benzofurans also had lower affinity at the 5-HTA1A receptor, but decreased only about 20-30% from that of the indole isosteres. Thus, the 5-HT1A receptor is less discriminating with respect to preference for an indole versus a benzofuran, although all of the compounds did have higher affinities for the 5-HT2 receptor than for the 5-HT1A receptor. It is suggested that benzofurans may be useful in the design of serotonin receptor ligands.