dimethyl (2E)-2-(diethylamino)but-2-enedioate | 996-85-0

• 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: dimethyl (2E)-2-(diethylamino)but-2-enedioate
• 英文别名: Dimethyl diethylaminomaleate；dimethyl (E)-2-(diethylamino)but-2-enedioate
• CAS: 996-85-0
• 化学式: C₁₀H₁₇NO₄
• 分子量: 215.249
• InChiKey: ODMUPYSKTVVGAR-BQYQJAHWSA-N

物化性质

• 沸点：
  70 °C(Press: 5 Torr)
• 密度：
  1.069±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl (2E)-2-(diethylamino)but-2-enedioate 、 4-叔丁基苯胺 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以85%的产率得到dimethyl 2-(p-tert-butylanilino)maleate
  参考文献：
  名称：

  Metal complexes of tetra(6-tert-butyl-2,3-quinolino)porphyrazine: I. Synthesis

  摘要：

  Complexes of tetra(6-tei-t-butyl-2,3-quinolino)porphyrazine with Cu, Co, Zn, and Ni soluble in hydrophobic liquids were synthesized for the first time by template tetramerization of derivatives of 6-tertbutylquinoline-2,3-dicarboxylic acid formed from the corresponding acid in the course of carbamide synthesis in presence of the bivalent metal ions.

  DOI：

  10.1134/s1070363208080252
• 作为产物：
  描述：

  cis-1,2-Bis-(methoxycarbonyl)vinyl-triethyl-ammonium 以 二氯甲烷 为溶剂， 生成 dimethyl (2E)-2-(diethylamino)but-2-enedioate
  参考文献：
  名称：

  Mono- and disubstituted vinyltrialkylammonium compounds. Synthesis and stereochemistry

  摘要：

  DOI：

  10.1021/jo00956a025

文献信息

• Efficient oxidative N -dealkylative addition of trialkylamines to dimethyl acetylenedicarboxylate using BrCCl 3 as the terminal oxidant
  作者：Fangnan Liu、Zhiguo Zhang、Zongbi Bao、Huabin Xing、Yiwen Yang、Qilong Ren

  DOI：10.1016/j.tetlet.2017.05.073

  日期：2017.7

  Herein we present a continuous improvement of visible-light mediated N-dealkylative addition of tertiary amines to dimethyl acetylenedicarboxylates (DMAD) using alkyl halogenides as external oxidants together with base additives. This method is highlighted by excellent tolerance with various tertiary amines and good to excellent yields in short reaction time under mild conditions.

  本文中，我们介绍了使用烷基卤化物作为外部氧化剂和基础添加剂，将可见光介导的叔胺N-去烷基化叔胺连续添加到乙炔二羧酸二甲酯（DMAD）中的方法。该方法的突出特点是对各种叔胺具有出色的耐受性，并且在温和的条件下，在较短的反应时间内即可获得良好的优异收率。
• Iodine Mediated Addition of Trialkylamines to Dimethyl Acetylenedicarboxylate
  作者：Quanping Wu、Hui-Fang Liu、Yue Zhang、Shiyu Shen、Song Xue

  DOI：10.2174/15701786113109990027

  日期：2013.9.1

  Addition reaction of tertiary amines to dimethyl acetylenedicarboxylate mediated by molecular iodine is described. The trialkylamines afford dealkylative adducts in moderate to good yields. Amines containing an aryl group react sluggishly in low yields with a loss of alkyl group.

  描述了由分子碘介导的叔胺与乙酰二羧酸二甲酯的加成反应。三烷基胺以中等至良好的产率提供脱烷基加合物。含有芳基的胺反应缓慢，收率低，烷基损失。
• Visible-Light-Mediated Dealkylative Coupling of Trialkylamines with Dialkyl Acetylenedicarboxylates
  作者：Zhiguo Zhang、Fangnan Liu、Zongbi Bao、Baogen Su、Huabin Xing、Qiwei Yang、Yiwen Yang、Qilong Ren

  DOI：10.1055/s-0036-1588704

  日期：——

  A dealkylative addition of trialkylamines to dialkyl acetylenedicarboxylates with eosin Y as a metal-free catalyst and molecular oxygen as the terminal oxidant was developed. This visible-light-mediated organocatalytic protocol is compatible with a wide variety of trialkylamines, giving the corresponding adducts in moderate to good yields.

  开发了以伊红 Y 作为无金属催化剂和分子氧作为末端氧化剂的三烷基胺与乙炔二羧酸二烷基酯的脱烷基加成反应。这种可见光介导的有机催化方案与多种三烷基胺兼容，以中等至良好的产率提供相应的加合物。
• The reaction betweentriazolobenzopyridinium and triazolothiazolium ylides with dimethyl acetylenedicarboxylate
  作者：Belén Abarca、Rafael Ballesteros、Nadia Houari、Aldelouahid Samadi

  DOI：10.1016/s0040-4020(98)00117-3

  日期：1998.4

  The reaction of some [1,2,3]triazolo[1,5-a]quinolinium 1,2, [1,2,3]triazolo[5,1-a]isoquinolinium3,4 and [1,2,3]triazolo[5,1-b]thiazolium 5,6 ylides with dimethyl acetylenedicarboxylate is described. Compounds as dimethyl pyrrolo[1,2-a]quinoline-1,2-dicarboxylate 19, dimethyl pyrrolo[2,1-a]isoquinoline-2,3-dicarboxylate 20, 1,1-dicyano-2,3-dimethoxycarbonyl-1H-pyrido[1,2-a]quinoline24, 4,4-dicyano-2

  一些[1,2,3]三唑并[1,5- a ]喹啉1,2，[1,2,3]三唑并[5,1- a ]异喹啉3,4和[1,2,3描述了带有乙炔二羧酸二甲酯的三唑并[5,1- b ]噻唑鎓5,6烷基化物。化合物如二甲基吡咯并[1,2一]喹啉-1,2-二羧酸二19，二甲基吡咯并[2,1-一个]异喹啉-2,3-二羧酸酯20，1,1-二氰基-2,3- dimethoxycarbonyl- 1 ħ -吡啶并[1,2一]喹啉24，4,4-二氰基-2,3-二甲氧基羰基4 ħ -吡啶并[2,1-一个]异喹啉如图25所示，形成7-甲基-5,6-二甲氧基-羰基吡咯并[2,1- a ]噻唑14b。
• Diels–Alder reactions of an elusive 1,3-butadiene bearing 2-carboxy and 4-alkoxy substituents
  作者：Szu-Han Chen、Che-Hsuan Chang、Jim-Min Fang

  DOI：10.1016/j.tetlet.2016.08.030

  日期：2016.9

  A reactive diene, ethyl 2-methylene-4-(pent-3-oxy)but-2-enoate, bearing electron-withdrawing carboxy and electron-donating pentoxy substituents is prepared and trapped in situ by a variety of dienophiles to form [4+2] cycloaddition products. Diels–Alder reaction of this diene with fumarate esters gives multiply substituted cyclohexenes that are useful for building the scaffold of oseltamivir.

  制备带有吸电子羧基和供电子戊氧基取代基的反应性二烯2-亚甲基-4-（戊-3-氧基）丁-2-烯酸乙酯，并通过各种双亲体将其原位捕获以形成[4] +2]环加成产物。该二烯与富马酸酯的Diels-Alder反应产生了多个取代的环己烯，可用于构建奥司他韦的骨架。