ethyl (2Z)-3-[(2-phenylethyl)amino]but-2-enoate | 217453-93-5

• 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: ethyl (2Z)-3-[(2-phenylethyl)amino]but-2-enoate
• 英文别名: ethyl (Z)-3-(2-phenylethylamino)but-2-enoate
• CAS: 217453-93-5
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: VVQDCZPXHJVNGV-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (2Z)-3-[(2-phenylethyl)amino]but-2-enoate 在 三氟甲磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.5h， 生成 11b-Methyl-4-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinoline-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  Architecturally diverse heterocycle formation by N-acyliminium ion initiated cyclization

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(03)01190-0
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2-苯乙胺 在 ammonium cerium(IV) nitrate 作用下， 反应 0.25h， 以94%的产率得到ethyl (2Z)-3-[(2-phenylethyl)amino]but-2-enoate
  参考文献：
  名称：

  一种用硝酸铈铵 (CAN) 烯胺化 1,3-二羰基化合物的有效方法

  摘要：

  已经描述了一种通过使用硝酸铈铵 (CAN) 作为催化剂来烯化 1,3-二羰基化合物的有效方法。在无溶剂条件下，在很短的反应时间内以优异的收率合成了多种 β-氨基-α,β-不饱和酮和酯。

  DOI：

  10.1002/jccs.200700127

文献信息

• An efficient chemo- and stereoselective synthesis of enaminones and enaminoesters using (bromodimethyl)sulfonium bromide under solvent-free conditions
  作者：Biswanath Das、Boddu Shashi Kanth、Anjoy Majhi、Kongara Ravinder Reddy

  DOI：10.1002/hc.20477

  日期：2008.9

  (Bromodimethyl)sulfonium bromide has efficiently been employed for chemo- and stereoselective conversions of β-dicarbonyl compounds into β-enaminones and β-enaminoesters by a treatment with amines at room temperature under solvent-free conditions. © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:630–633, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20477

  （溴二甲基）溴化锍已有效地用于通过在室温下在无溶剂条件下用胺处理将 β-二羰基化合物化学和立体选择性转化为 β-烯胺酮和 β-烯胺酯。© 2008 Wiley Periodicals, Inc. 杂原子化学 19:630–633, 2008; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20477
• Hadden, Mark; Nieuwenhuyzen, Mark; Potts, Deirdre, Journal of the Chemical Society. Perkin transactions I, 1998, # 20, p. 3437 - 3441
  作者：Hadden, Mark、Nieuwenhuyzen, Mark、Potts, Deirdre、Stevenson, Paul J.

  DOI：——

  日期：——
• β-Enaminoesters as Novel Corrosion Inhibitors for Carbon Steel in Acidic Medium
  作者：Mariana Carlos、Arthur Valbon、Marcelo Neves、Margareth Santos、Aurea Echevarria

  DOI：10.21577/0103-5053.20180133

  日期：——

  In this work, two beta-enaminoesters, EN1 and EN2, were synthesized, characterized and their anticorrosion effects on American Iron and Steel Institute (AISI) 1020 carbon steel in 0.5 mol L-1 HCl were investigated using gravimetric and electrochemical methods. The results revealed that both compounds inhibit corrosion. Good correlations were observed between results obtained for gravimetric and electrochemical methods. EN1 exhibited highest efficiency of 98% after 24 h of immersion in HCl solution. The adsorption of compounds on steel surface followed the modified Langmuir adsorption isotherm. Surface morphology of carbon steel was examined using scanning electron microscopy showing that the metal surface was protected by EN1 as inhibitor of corrosion.
• An Efficient Method for the Enamination of 1,3-Dicarbonyl Compounds with Ceric Ammonium Nitrate (CAN)
  作者：Li-Ping Mo、Shu-Fen Liu、Wan-Zhi Li

  DOI：10.1002/jccs.200700127

  日期：2007.8

  An efficient method for the enamination of 1,3-dicarbonyl compounds by employing ceric ammonium nitrate (CAN) as the catalyst has been described. A variety of β-amino-α,β-unsaturated ketones and esters have been synthesized in excellent yield within a short reaction time under solvent-free conditions.

  已经描述了一种通过使用硝酸铈铵 (CAN) 作为催化剂来烯化 1,3-二羰基化合物的有效方法。在无溶剂条件下，在很短的反应时间内以优异的收率合成了多种 β-氨基-α,β-不饱和酮和酯。
• 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.