N-(1,2-双(3,4-二甲氧基苯基)乙基)甲酰胺 | 76306-70-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: N-(1,2-双(3,4-二甲氧基苯基)乙基)甲酰胺
• 英文名称: N-<1,2-bis(3,4-dimethoxyphenyl)ethyl>formamide
• 英文别名: N-1,2-bis(3,4-dimethoxyphenyl)ethylformamide；N-(3,4,3',4'-tetramethoxy-bibenzyl-α-yl)-formamide；N-(3,4,3',4'-Tetramethoxy-bibenzyl-α-yl)-formamid；N-Formyl-1,2-bis-<3,4-dimethoxy-phenyl>-aethylamin；1,2-Bis-(3,4-dimethoxy-phenyl)-1-formyl-aminoethan；1,2-Bis(3,4-dimethoxyphenyl)ethylformamide；N-[1,2-bis(3,4-dimethoxyphenyl)ethyl]formamide
• CAS: 76306-70-2
• 化学式: C₁₉H₂₃NO₅
• 分子量: 345.395
• InChiKey: LNFPBETXSXYHCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(1,2-双(3,4-二甲氧基苯基)乙基)甲酰胺 在 盐酸 、 potassium carbonate 作用下， 生成 1,2-bis(3,4-dimethoxyphenyl)-N-(2,2-diethoxyethyl)ethylamine
  参考文献：
  名称：

  Waldmann; Chwala, Justus Liebigs Annalen der Chemie, 1957, vol. 609, p. 125,141

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-bis(3,4-dimethoxyphenyl)ethanone 生成 N-(1,2-双(3,4-二甲氧基苯基)乙基)甲酰胺
  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

• Isoquinoline formation via iminium ions cyclization: A direct approach to c-2′ functionalized 3-aryltetrahydroisoquinolines
  作者：Nuria Sotomayor、Esther Domínguez、Esther Lete

  DOI：10.1016/0040-4020(95)00770-9

  日期：1995.10

  3-Aryltetrahydroisoquinoline derivatives can be efficiently prepared by titanium tetrachloride promoted cyclization of N-methoxymethyl-N-1,2-diarylethylamines via iminium ions. In the case of primary amines, the 1-aryl group prevents the alkylation of a second iminium ion, avoiding dimerization. The mild reaction conditions are compatible with the presence of acid sensitive groups; thus, the 2′-functionalized

  3-芳基四氢异喹啉衍生物可通过四氯化钛通过亚胺离子促进N-甲氧基甲基-N -1,2-二芳基乙胺的环化反应而有效地制备。在伯胺的情况下，1-芳基防止第二亚胺离子的烷基化，避免二聚。温和的反应条件与酸敏感基团的存在相适应。因此，可以高产率地制备2'-官能化的3-芳基四氢异喹啉6a而无需甲硅烷基化。因此，这是质子酸催化的Pictet-Spengler方法的一个很好的选择，当将其应用于2'-官能化胺时，甲硅烷基化的3-芳基四氢异喹啉4的收率低3a。
• Towards the rehabilitation of the Leuckart reductive amination reaction using microwave technology
  作者：André Loupy、Daphné Monteux、Alain Petit、Jesús Ma Aizpurua、Esther Domínguez、Claudio Palomo

  DOI：10.1016/0040-4039(96)01865-5

  日期：1996.11

  amination of carbonyl compounds was dramatically enhanced with respect to conventional heating by a specific microwave effect when the reaction was performed, under solvent-free conditions, in a monomode microwave reactor. Excellent isolated yields (up to 97%) were attained within short reaction times (typically, 30 minutes)

  当在无溶剂条件下在单模微波反应器中进行反应时，通过特定的微波效应，相对于常规加热，羰基化合物的Leuckart还原胺化得到了显着增强。在较短的反应时间内（通常为30分钟）即可获得出色的分离产率（高达97％）
• Structure and stereochemistry of cyclodimers obtained by acid treatment of trans-stilbenes and of N-1,2-diarylethylamides
  作者：José M. Aguirre、Elba N. Alesso、Graciela Y. Moltrasio Iglesias

  DOI：10.1039/a900282k

  日期：——

  The reaction of trans-stilbenes and N-1,2-diarylethylamides with ethyl polyphosphate affords indanes and tetralins with three stereogenic centres. The structural and configurational assignment of the cyclodimers is based mainly on the NMR and MS data. A possible transition state for the reaction is discussed.

  反式二苯乙烯和 N-1,2-二乙基酰胺与多磷酸乙酯反应生成具有三个立体中心的茚和四氢萘。环二聚体的结构和构型分配主要基于核磁共振和质谱数据。讨论了该反应可能的过渡态。
• Villa, Maria Jesus; Dominguez, Esther; Lete, Esther, Heterocycles, 1986, vol. 24, # 7, p. 1943 - 1954
  作者：Villa, Maria Jesus、Dominguez, Esther、Lete, Esther

  DOI：——

  日期：——
• Application of the Intramolecular α-Amidoalkylation Reaction for the Synthesis of 3- and 1,3-Alkyl(aryl) 2-Formyltetrahydroisoquinolines
  作者：Atanas P. Venkov、Ilian I. Ivanov

  DOI：10.1080/00397919308011269

  日期：1993.6

  3- and 1,3-Alkyl(aryl) 2-Formyltetrahydroisoquinolines 6 are obtained by the application of the intramolecular is-proportional-to -amidoalkylation reaction from 1-Alkyl(Aryl)-2-Arylethylformamides 2 and aldehydes in acidic medium.