(Z)-3-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-but-2-enoic acid ethyl ester | 604763-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-3-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-but-2-enoic acid ethyl ester
• 英文别名: ethyl (Z)-3-[2-(3,4-dimethoxyphenyl)ethylamino]but-2-enoate
• CAS: 604763-51-1
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: FSMABDYVJUINMN-BENRWUELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-3-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-but-2-enoic acid ethyl ester 在 磷酸 作用下， 反应 3.0h， 以71%的产率得到(6,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-acetic acid ethyl ester
  参考文献：
  名称：

  1,1-Disubstituted Tetrahydroisoquinolines from Enaminones via Pictet–Spengler Reaction

  摘要：

  Enaminones, prepared by condensation of homoveratrylamine with 1,3-dicarbonyl compounds, undergo intramolecular cyclization in acidic media to afford 1,1-disubstituted tetrahydroisoquinolines in good yields. Further modification of the title compounds is demonstrated.

  DOI：

  10.1081/scc-120022477
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 3,4-二甲氧基苯乙胺 在 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 生成 (Z)-3-[2-(3,4-Dimethoxy-phenyl)-ethylamino]-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  1,1-Disubstituted Tetrahydroisoquinolines from Enaminones via Pictet–Spengler Reaction

  摘要：

  Enaminones, prepared by condensation of homoveratrylamine with 1,3-dicarbonyl compounds, undergo intramolecular cyclization in acidic media to afford 1,1-disubstituted tetrahydroisoquinolines in good yields. Further modification of the title compounds is demonstrated.

  DOI：

  10.1081/scc-120022477

文献信息

• Synthesis of Unsymmetrical β-Enamino Ketones
  作者：Atanas P. Venkov、Plamen A. Angelov

  DOI：10.1055/s-2003-41067

  日期：——

  A convenient procedure for modification of β-enaminones by α-C-acylation and subsequent acidic cleavage is described. The unsymmetrical β-enamino ketones obtained in this way could be hydrolyzed to provide an entry towards various unsymmetrical 1,3-diketones.

  本文介绍了一种通过δ-C-酰化和随后的酸性裂解来修饰δ-烯氨基酮的简便程序。通过这种方法得到的非对称δ-烯氨基酮可以通过水解得到各种非对称的 1,3-二酮。
• Architecturally diverse heterocycle formation by N-acyliminium ion initiated cyclization
  作者：Matthew M Abelman、Jeffrey K Curtis、Donald R James

  DOI：10.1016/s0040-4039(03)01190-0

  日期：2003.8

  Enaminoesters containing a tethered indole or aryl moiety on the amine react with substituted maleic anhydrides or acryloyl chlorides to provide pyrrolinone or dihydropyridone products, respectively. The indole-tethered dihydropyridones can be induced to undergo a one-pot cyclization whereas, the indole-tethered pyrrolinone intermediates are readily cyclized with HCl. The aryl-tethered pyrrolinones or dihydropyridones can be isolated and subsequently induced to cyclize with triflic acid. This methodology culminates in the synthesis of erythrane-like and other natural products that are readily amenable to combinatorial library production. (C) 2003 Elsevier Ltd. All rights reserved.