ethyl 3-(4-bromophenylamino)but-2-enoate | 158261-85-9

• 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 3-(4-bromophenylamino)but-2-enoate
• 英文别名: ethyl (Z)-3-(4-bromoanilino)but-2-enoate
• CAS: 158261-85-9
• 化学式: C₁₂H₁₄BrNO₂
• 分子量: 284.153
• InChiKey: DYXBVRCUZPTNDT-HJWRWDBZSA-N

物化性质

• 熔点：
  53-55 °C
• 沸点：
  352.0±42.0 °C(predicted)
• 密度：
  1.389±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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 3-(4-bromophenylamino)but-2-enoate 在 sodium 、 异丙醇 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到3-Anilino-1-butanol
  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 、 4-溴苯胺 在 ytterbium(III) triflate 作用下， 反应 6.0h， 以92%的产率得到ethyl 3-(4-bromophenylamino)but-2-enoate
  参考文献：
  名称：

  无溶剂条件下Yb(OTf)3催化β-烯氨基酯的高效合成方法

  摘要：

  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。

  DOI：

  10.1071/ch06239

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。
• 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。
• Phosphotungstic Acid Catalysed Synthesis of β-Enamino Compounds under Solvent-Free Conditions
  作者：Geng-Chen Li

  DOI：10.3184/030823407x273488

  日期：2007.12

  developed for the synthesis of β-enaminones and β-enamino esters by reacting 1,3-dicarbonyl compounds with amines in the presence of catalytic amounts of phosphotungstic acid (H3PW12O40, 1 mol%). The reaction proceeds smoothly at room temperature under solvent-free conditions and gives the corresponding β-enamino compounds in high to excellent yields.

  在催化量的磷钨酸 (H3PW12O40, 1 mol%) 存在下，通过使 1,3-二羰基化合物与胺反应，开发了一种方便的环保程序，用于合成 β-烯胺酮和 β-烯胺酯。该反应在室温下无溶剂条件下顺利进行，并以高产率获得相应的 β-烯氨基化合物。
• ZrCl4-Catalyzed Efficient Synthesis of Enaminones and Enamino Esters under Solvent-free Conditions
  作者：Jin Lin、Li-Feng Zhang

  DOI：10.1007/s00706-006-0565-2

  日期：2007.1

  A facile synthesis of beta-enaminones and enamino esters by condensation of beta-dicarbonyl compounds with differently substituted amines in the presence of ZrCl4 under solvent-free conditions is reported.