ethyl 2-(phenylamino)cyclopent-1-enecarboxylate | 52909-66-7

• 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 2-(phenylamino)cyclopent-1-enecarboxylate
• 英文别名: 1-Cyclopentene-1-carboxylic acid, 2-(phenylamino)-, ethyl ester；ethyl 2-anilinocyclopentene-1-carboxylate
• CAS: 52909-66-7
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: RNDODFVKQYVWSO-UHFFFAOYSA-N

物化性质

• 沸点：
  348.8±42.0 °C(Predicted)
• 密度：
  1.173±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• 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 2-(phenylamino)cyclopent-1-enecarboxylate 生成 2,3-Dihydro-1H-cyclopentachinolin-9-ol
  参考文献：
  名称：

  Blount; Perkin; Plant, Journal of the Chemical Society, 1929, p. 1983

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氧代环戊羧酸乙酯 在 无水氯化钙 、 苯胺 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 2-(phenylamino)cyclopent-1-enecarboxylate
  参考文献：
  名称：

  Polycyclic compounds

  摘要：

  公式（I）的化合物，其制备方法，制药配方及其用途。 ##STR1##

  公开号：

  US06130228A1

文献信息

• Visible Light Promoted β-C-H Alkylation of β-Ketocarbonyls <i>via</i> a β-Enaminyl Radical Intermediate
  作者：Dehong Wang、Long Zhang、Sanzhong Luo

  DOI：10.1002/cjoc.201700785

  日期：2018.4

  carbonyl activation mode is reported on the basis of photo‐induced single‐electron‐transfer (SET) oxidation of a secondary enamine. The resultant β‐enaminyl radical intermediate was trapped by a wide range of Michael acceptors, producing β‐alkylation products of β‐ketocarbonyls in a highly efficient manner.

  在仲烯胺的光诱导单电子转移（SET）氧化的基础上报道了5πe羰基活化模式。生成的β-烯丙基自由基中间体被多种Michael受体捕获，从而以高效方式生成β-酮羰基的β-烷基化产物。
• A General and Efficient Method for the Preparation of β-Enamino Ketones and Esters Catalyzed by Indium Tribromide
  作者：Zhan-Hui Zhang、Liang Yin、Yong-Mei Wang

  DOI：10.1002/adsc.200505268

  日期：2006.1

  A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide. The reaction proceeds smoothly at room temperature in a short reaction time under solvent-free conditions.

  在催化量的三溴化铟存在下，通过使β-二羰基化合物与胺反应，可以高产率地合成出多种β-烯胺酮和酯。在无溶剂条件下，反应在室温下以短的反应时间平稳地进行。
• Zn(ClO₄)₂·6H₂O as a Powerful Catalyst for the Conversion of β-Ketoesters into β-Enamino Esters
  作者：Giuseppe Bartoli、Letizia Sambri、Marcella Bosco、Manuela Locatelli、Enrico Marcantoni、Paolo Melchiorre

  DOI：10.1055/s-2003-44974

  日期：——

  Zn(ClO 4 ) 2 .6H 2 O proved to be a very powerful catalyst for the condensation of primary and secondary amines with β-ketoesters to give N-substituted β-enaminoesters.

  Zn(ClO 4 ) 2 .6H 2 O 被证明是伯胺和仲胺与 β-酮酯缩合生成 N-取代 β-烯氨基酯的非常有效的催化剂。
• Regio- and stereoselective double alkylation of β-enamino esters with organolithium reagents followed by one-pot reduction: convenient method for the synthesis of tertiary γ-amino alcohols
  作者：Cristina Cimarelli、Gianni Palmieri、Emanuela Volpini

  DOI：10.1016/j.tet.2006.07.044

  日期：2006.10

  stereoselective procedure for the preparation of tertiary γ-amino alcohols starting from β-enamino esters is presented. In this procedure, the double alkylation of β-enamino esters with organolithium reagents is followed by one-pot reduction with sodium borohydride in methanol/acetic acid. A hypothesis of mechanism is given, explaining the observed diastereoselectivity through molecular modeling. The configuration

  提出了一种简单，高产且立体选择性的方法，该方法可从β-烯胺酯开始制备叔γ-氨基醇。在该方法中，用有机锂试剂对β-烯胺酯进行双烷基化，然后用硼氢化钠在甲醇/乙酸中一锅还原。给出了机理的假设，通过分子建模解释了观察到的非对映选择性。产物的构型通过1 H NMR光谱结合构象分析确定。
• 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。