(+/-)-N-acetyl-α-phenyl-β-(3,4-dimethoxy)phenethylamine | 76306-60-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (+/-)-N-acetyl-α-phenyl-β-(3,4-dimethoxy)phenethylamine
• 英文别名: N-<2-(3,4-dimethoxyphenyl)-1-phenylethyl>acetamide；N-(3',4'-dimethoxy-bibenzyl-α-yl)-acetamide；N-(3',4'-Dimethoxy-bibenzyl-α-yl)-acetamid；α'-Acetamino-3.4-dimethoxy-bibenzyl；N-[2-(3,4-dimethoxyphenyl)-1-phenylethyl]acetamide
• CAS: 76306-60-0
• 化学式: C₁₈H₂₁NO₃
• 分子量: 299.37
• InChiKey: MLJVECCOBHWDTE-UHFFFAOYSA-N

物化性质

• 沸点：
  480.7±45.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (+/-)-N-acetyl-α-phenyl-β-(3,4-dimethoxy)phenethylamine 在 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 8,9-Dimethoxy-10b-methyl-5-phenyl-6,10b-dihydro-5H-oxazolo[2,3-a]isoquinoline-2,3-dione
  参考文献：
  名称：

  A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines

  摘要：

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

  DOI：

  10.1021/jo00021a014
• 作为产物：
  描述：

  2-(3,4-dimethoxyphenyl)-1-phenylethanone 在 盐酸 、 sodium hydroxide 作用下， 生成 (+/-)-N-acetyl-α-phenyl-β-(3,4-dimethoxy)phenethylamine
  参考文献：
  名称：

  A modified Bischler-Napieralski procedure for the synthesis of 3-aryl-3,4-dihydroisoquinolines

  摘要：

  A modification of the Bischler-Napieralski reaction for the cyclization of (1,2-diphenylethyl)amides to the 3-aryl-3,4-dihydroisoquinolines is presented. Elimination of the amide group as the nitrile via the retro-Ritter reaction is avoided by its conversion to an N-acyliminium intermediate with oxalyl chloride-FeCl3. Removal of the oxalyl group in refluxing MeOH-sulfuric acid provides the 3,4-dihydroisoquinolines in moderate to high yields. The method is also highly effective with (2-phenylethyl)amides.

  DOI：

  10.1021/jo00021a014

文献信息

• (±)α-Phenyl-β-(3,4-dimethoxy)- and (±)α-Phenyl-β-(3,4-dihydroxy)phenethylamines: Potential Probes for Nicotinic Acetylcholine Receptor-Ion Channel Molecule from Torpedo Electric Organ
  作者：Ragab M. Shafik、Raafat Soliman、Soad A. El-Hawash、Samia A. El-Dardiry、Shebl Sherby

  DOI：10.1002/jps.2600761017

  日期：1987.10

  N-alkyl derivatives of (+/-)alpha-phenyl-beta-(3,4-dimethoxy)- and (+/-)alpha-phenyl-beta-(3,4-dihydroxy)-phenethylamines was achieved. These compounds were shown to bear certain structural features of acetylcholine (ACh), as well as phencyclidine (PCP). The latter was reported to act as a specific probe for the nicotinic ACh receptor-ion channel molecule from Torpedo electric organ. Biochemical binding

  （+/-）α-苯基-β-（3,4-二甲氧基）-和（+/-）α-苯基-β-（3,4-二羟基）的一些N-甲基，N-烷基衍生物的合成）-苯乙胺。这些化合物显示具有乙酰胆碱（ACh）和苯环利定（PCP）的某些结构特征。据报道后者可作为鱼雷电器官中烟碱型ACh受体离子通道分子的特异性探针。生化结合研究表明，对于烟碱型ACh受体，3,4-二甲氧基衍生物可作为[3H] ACh结合相互作用的阻滞剂，而3,4-二羟基类似物可刺激这种结合。另一方面，所有测试的苯乙胺均表现出对[3H] PCP结合相互作用的有效阻断作用。
• Lettre; Fernholz, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1943, vol. 278, p. 175,197
  作者：Lettre、Fernholz

  DOI：——

  日期：——
• Narasimhan, N. S.; Wadia, M. S.; Shete, N. R., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 7, p. 556 - 560
  作者：Narasimhan, N. S.、Wadia, M. S.、Shete, N. R.

  DOI：——

  日期：——
• NARASIMHAN N. S.; WADIA M. S.; SHETE N. R., INDIAN J. CHEM., 1980, B 19, NO 7, 556-560
  作者：NARASIMHAN N. S.、 WADIA M. S.、 SHETE N. R.

  DOI：——

  日期：——