diethyl N-butyliminodiacetate | 100247-94-7

• 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 N-butyliminodiacetate
• 英文别名: Butylimino-diessigsaeure-diaethylester；Ethyl 2-[butyl-(2-ethoxy-2-oxoethyl)amino]acetate
• CAS: 100247-94-7
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: DMEGDTPMVBOJLT-UHFFFAOYSA-N

物化性质

• 沸点：
  100-105 °C(Press: 1.1 Torr)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  diethyl N-butyliminodiacetate 在 三乙醇胺 、 sodium ethanolate 、 potassium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 2-butyl-5,10-dihydro-2H-benzo[6,7][1,4]dioxocino[2,3-c]pyrrole
  参考文献：
  名称：

  新型3,4-亚烷基二氧吡咯（ADOP）衍生物的合成与计算带隙工程及其电致变色性能研究

  摘要：

  This research highlights the degree of conformity between our electrochemical and theoretical studies conducted on the newly designed electropolymerizable monomers (BuDOP, BenDOP and BenzoDOP) possessing 3,4-alkylenedioxypyrrole (ADOP) backbone (BuDOP). We tried to select logical enhancing of the structures in a stepwise in order to discuss the effects of benzene (BenDOP) and benzodioxane (BenzoDOP) like aromatic subunits to the electrochromic properties of the target monomers. Following to the completion of the synthetic steps, appropriate structural analyses of monomers were performed (FT-IR, GC-MS, H-1-NMR, C-13-NMR). Subsequently, their corresponding polymers were prepared by electrochemical oxidation and characterized. Afterwards, our consecutive efforts have been contributed to theoretical studies in order to obtain information about their structural properties. To this aim, geometry optimizations were carried out using hybrid density functional theory (DFT/B3LYP/LANL2DZ) and HOMO, LUMO energy levels, HOMO-LUMO energy gaps (Delta E), electron affinity (EA) as well as ionization potential (IP) values were calculated. Theoretical data were then used for identifying the structure-electronic properties relationship and we aimed to determine the electrochromic properties of the studied monomers. Our results from the B3LYP/LANL2DZ calculations indicated that P(BenDOP) has the lowest HOMO-LUMO gap and we predicted that theoretical data were in good agreement with the experimental studies. (C) 2016 The Electrochemical Society. All rights reserved.

  DOI：

  10.1149/2.0131610jes
• 作为产物：
  描述：

  溴乙酸乙酯 、 正丁胺 以 苯 为溶剂， 生成 diethyl N-butyliminodiacetate
  参考文献：
  名称：

  N-Substituted Glycinate and Alaninate Esters

  摘要：

  DOI：

  10.1021/jo01075a014

文献信息

• Iridium Porphyrin Catalyzed N–H Insertion Reactions: Scope and Mechanism
  作者：Bernie J. Anding、L. Keith Woo

  DOI：10.1021/om400098v

  日期：2013.5.13

  Ir(TTP)CH3 catalyzed N–H insertion reactions between ethyl diazoacetate (EDA) or methyl phenyldiazoacetate (MPDA) and a variety of aryl, aliphatic, primary, and secondary amines to generate substituted glycine esters with modest to high yields. Aniline substrates generally gave yields above 80%, with up to 105 catalyst turnovers, and without slow addition of the diazo reagent. Good yields were also achieved

  Ir（TTP）CH 3催化重氮乙酸乙酯（EDA）或苯基重氮乙酸甲酯（MPDA）与各种芳基，脂肪族，伯和仲胺之间的N–H插入反应，以中等至高收率生成取代的甘氨酸酯。苯胺底物的收率通常超过80％，催化剂的转化率高达10 5，并且没有缓慢添加重氮试剂。尽管在某些情况下需要更高的催化剂负载量和胺的缓慢添加，但脂肪族胺也能获得良好的收率。伯胺与EDA反应生成单，双-插入产品，其中任一个的可在高产率下的化学计量比和反应温度的适当选择有选择地来制备。值得注意的是，混合三取代胺RN（CH通过在伯胺中插入1当量的EDA和1当量的MPDA生成2 CO 2 Et）（CHPhCO 2 Me）。使用底物竞争研究，捕获实验和多种光谱技术检查了N–H插入机制。使用具有EDA或MPDA的成对胺进行的底物竞争研究显示HammeTT相关性分别具有ρ= 0.15和ρ + = -0.56的斜率以及k H / k D的动力学同位素比=