(Z)-ethyl 3-(p-tolylamino)but-2-enoate | 158261-84-8

• 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)-ethyl 3-(p-tolylamino)but-2-enoate
• 英文别名: Ethyl (2z)-3-(4-toluidino)-2-butenoate；ethyl (Z)-3-(4-methylanilino)but-2-enoate
• CAS: 158261-84-8
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: RQPDERZDULBYRE-LUAWRHEFSA-N

物化性质

• 沸点：
  324.9±42.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  (Z)-ethyl 3-(p-tolylamino)but-2-enoate 在 三乙酰氧基硼氢化钠 作用下， 以 溶剂黄146 为溶剂， 反应 2.0h， 以65%的产率得到3-[N-(4-甲基苯基)氨基]丁酸乙酯
  参考文献：
  名称：

  Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters

  摘要：

  Convenient procedures for the chemo- and diastereoselective reduction of beta-enamino esters 1 are described. Both cis- and trans-gamma-amino alcohols 2 or beta-amino esters 3 can be prepared by reduction of beta-enamino esters 1, readily available starting materials, with the use of inexpensive reagents Nali-PrOH or NaHbB(OAc)(3)/AcOH, respectively, and the appropriate reduction conditions. The mechanisms and diastereoselectivities for the reductions are discussed. The relative configurations and conformations of the diastereoisomeric gamma-amino alcohols 2 and beta-amino esters 3 obtained are established by H-1 and C-13 NMR study and unequivocally set by their cyclic derivatives tetrahydro-1,3-oxazines 4.

  DOI：

  10.1021/jo00097a039
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 乙烷,三氯氟- 在 indium(III) bromide 作用下， 反应 0.67h， 以95%的产率得到(Z)-ethyl 3-(p-tolylamino)but-2-enoate
  参考文献：
  名称：

  三溴化铟催化制备β-烯氨基酮和酯的通用有效方法

  摘要：

  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。

  DOI：

  10.1002/adsc.200505268

文献信息

• Efficient Synthetic Method for β-Enamino Esters Catalyzed by Yb(OTf)3 under Solvent-Free Conditions
  作者：Ravi Varala、Sreelatha Nuvula、Srinivas R. Adapa

  DOI：10.1071/ch06239

  日期：——

  esters have been synthesized in moderate to excellent yields by reacting 1,3-dicarbonyl compounds with amines in the presence of catalytic amounts of Yb(OTf)3 (2 mol%). The reaction proceeds smoothly at ambient temperature under solvent-free conditions. The catalyst can be recovered and reused.

  在催化量的 Yb(OTf)3 (2 mol%) 存在下，通过 1,3-二羰基化合物与胺反应，以中等至极好的产率合成了多种 β-烯氨基酯。该反应在环境温度下在无溶剂条件下顺利进行。催化剂可以回收再利用。
• A novel enamination of β-dicarbonyl compounds catalyzed by Bi(TFA)₃ immobilized on molten TBAB
  作者：Mohammad M Khodaei、Ahmad R Khosropour、Mehdi Kookhazadeh

  DOI：10.1139/v05-021

  日期：2005.3.1

  Enamination of a wide variety of primary amines was successfully carried out in the presence of catalytic amounts of bismuth(III) trifluoroacetate immobilized on molten tetrabutylammonium bromide as "green" media under mild conditions. This new system of the catalyst is recyclable and reusable. Generally, the results of the reaction in tetrabutylammonium bromide is better than the previously obtained

  在催化量的三氟乙酸铋 (III) 固定在作为“绿色”介质的熔融四丁基溴化铵上，在温和条件下成功地进行了多种伯胺的烯化。这种新的催化剂系统是可回收和可重复使用的。一般来说，在四丁基溴化铵中的反应结果由于其产率和反应时间而优于先前在水中获得的结果。关键词：胺、铋化合物、β-二羰基化合物、烯化、离子液体。
• Enamination of β-Dicarbonyl Compounds with Amines
  作者：M. M. Khodaei、A. R. Khosropour、C. Cardel

  DOI：10.1002/jccs.200800032

  日期：2008.2

  Enamination of a wide variety of primary amines was successfully described with excellent chemo-selectivity in the presence of catalytic amounts of β-cyclodextrin in water under mild conditions. Aliphatic amines also reacted efficiently to produce the corresponding enaminones.

  在温和条件下，在水中存在催化量的 β-环糊精的情况下，成功地描述了多种伯胺的烯胺化，具有优异的化学选择性。脂肪胺也有效地反应产生相应的烯胺酮。
• 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。
• Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate
  作者：Cheng-Liang Feng、Ning-Ning Chu、Shu-Guang Zhang、Jin Cai、Jun-Qing Chen、Hua-You Hu、Min Ji

  DOI：10.2478/s11696-014-0544-8

  日期：2014.1.1

  A novel application of highly stable Fe(OTf)3 as an efficient catalyst for the synthesis of a variety of β-enamino ketones and esters under solvent-free conditions is described. Notably, this protocol of a “green synthesis”, which produced β-enamino ketones and esters by the reaction of a variety of β-dicarbonyl compounds and primary amines, exhibits attractive properties including high yields, short

  描述了一种高度稳定的Fe（OTf）3作为无催化剂条件下合成各种β-烯胺酮和酯的有效催化剂的新型应用。值得注意的是，这种“绿色合成”方案是通过多种β-二羰基化合物与伯胺的反应生成β-烯酮和酯，具有诱人的性能，包括高收率，较短的反应时间，较低的催化剂负载量和化学和区域选择性。另外，催化剂易于从反应系统中回收，并易于重新使用而活性损失最小。