diethyl 2-(phenyl(phenylamino)methyl)malonate | 58929-06-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 2-(phenyl(phenylamino)methyl)malonate
• 英文别名: Diethyl [anilino(phenyl)methyl]malonate；diethyl 2-[anilino(phenyl)methyl]propanedioate
• CAS: 58929-06-9
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: VCLKMTAYMZUWSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(phenyl(phenylamino)methyl)malonate 生成 N-苄叉苯胺 、 丙二酸二乙酯
  参考文献：
  名称：

  Wayne; Cohen, Journal of the Chemical Society, 1925, vol. 127, p. 458

  摘要：

  DOI：
• 作为产物：
  描述：

  丙二酸二乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 哌啶 作用下， 生成 diethyl 2-(phenyl(phenylamino)methyl)malonate
  参考文献：
  名称：

  α-Aminoalkanesulfonic Acids^1,2

  摘要：

  DOI：

  10.1021/jo01094a029

文献信息

• Bromodimethylsulfonium Bromide Catalyzed Three-Component Mannich-Type Reactions
  作者：Abu T. Khan、Tasneem Parvin、Lokman H. Choudhury

  DOI：10.1002/ejoc.200700643

  日期：2008.2

  Bromodimethylsulfonium bromide catalyzes Mannich-type reactions of a variety of aldimines, generated in situ from aldehydes and anilines, with enolizable ketones or diethyl malonate in three-component reactions to afford the corresponding β-amino carbonyl compounds. The salient features of this protocol are: shorter reaction times, simplicity of the procedure, good to excellent yields, avoidance of

  溴化二甲基锍溴化物催化由醛和苯胺原位生成的各种醛亚胺的曼尼希型反应，与可烯醇化的酮或丙二酸二乙酯在三组分反应中得到相应的 β-氨基羰基化合物。该方案的显着特点是：反应时间更短、程序简单、产率好到极好、避免了水处理和柱色谱分离，以及高立体选择性。（© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim , 德国, 2008)
• An efficient synthesis of β-amino esters via Zn(OTf)2-catalyzed Mannich-type reaction
  作者：Wang-Ge Shou、Yun-Yun Yang、Yan-Guang Wang

  DOI：10.1016/j.tetlet.2005.12.136

  日期：2006.3

  A Zn(OTf)2-catalyzed Mannich-type reaction of the electron-deficient aromatic amines with the electron-deficient aromatic aldehydes and diethyl malonic ester was described. This three-component reaction afforded the corresponding β-amino esters in good yields.

  描述了Zn（OTf）2催化的缺电子芳族胺与缺电子芳族醛和二乙基丙二酸酯的曼尼希型反应。该三组分反应以良好的产率提供了相应的β-氨基酯。
• Synthesis of β-amino carbonyl compounds via a Zn(OTf)2-catalyzed cascade reaction of anilines with aromatic aldehydes and carbonyl compounds
  作者：Yun-Yun Yang、Wang-Ge Shou、Yan-Guang Wang

  DOI：10.1016/j.tet.2006.08.063

  日期：2006.10

  Zn(OTf)2-catalyzed cascade reaction of anilines with aromatic aldehydes and carbonyl compounds was described. This one-pot three-component reaction afforded the corresponding β-amino carbonyl compounds, β-amino esters, and β-amino ketones in good to excellent yields. The reaction was also applied for the liquid-phase synthesis of β-amino carbonyl compound library using PEG as a support.

  描述了Zn（OTf）2催化的苯胺与芳族醛和羰基化合物的级联反应。该一锅三组分反应以良好至优异的产率提供了相应的β-氨基羰基化合物，β-氨基酯和β-氨基酮。该反应还用于以PEG为载体的β-氨基羰基化合物库的液相合成。
• One-Pot Synthesis of β-Amino Esters by Recyclable Magnetic Organocatalyst-Catalysed Mannich-Type Reaction
  作者：Yibo Huang、Dan Guan、Liang Wang

  DOI：10.3184/174751914x13968767247911

  日期：2014.5

  L-cysteine supported on an iron oxide magnetic nanoparticle was prepared by a facile and simple method. The catalyst was effectively applied to the one-pot synthesis of β-amino esters in moderate to good yield. Moreover, the magnetic organocatalyst could be readily recovered and reused up to five times without significant loss of its catalytic activity.

  采用简单易行的方法制备了以氧化铁磁性纳米粒子为载体的 L-半胱氨酸。该催化剂被有效地应用于β-氨基酯的一锅合成，产率为中等至良好。此外，该磁性有机催化剂可随时回收并重复使用达五次，且其催化活性不会明显降低。
• One-Pot Synthesis of Mannich Bases Under Solvent-Free Conditions
  作者：Onur Demirkol、Dilek Akbaşlar、Sultan Giray、B. Barış Anıl

  DOI：10.1080/00397911.2013.853191

  日期：2014.5.3

  Abstract A mild and practically convenient one-pot procedure for the Mannich reaction via condensation of amines, aldehydes and malonates, β-ketoesters, or β-dicarbonyl compounds has been carried out without using any organic solvent, metallic catalyst, or Lewis acids or bases at room temperature. The present protocol offers several advantages, such as goods yields, simple procedure with easy workup

  摘要 在不使用任何有机溶剂、金属催化剂或路易斯酸或碱的情况下，通过胺、醛和丙二酸酯、β-酮酯或β-二羰基化合物的缩合，进行了一种温和且实用的曼尼希反应一锅法。在室温下。本协议提供了几个优点, 如货物产量、简单的程序、易于处理、不存在任何挥发性、危险的有机溶剂和金属催化剂。图形概要