3-((2-(Dimethylamino)ethyl)benzylamino)propionic acid | 127141-10-0

• 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: 3-((2-(Dimethylamino)ethyl)benzylamino)propionic acid
• 英文别名: N-benzyl-N-[2-(dimethylamino)ethyl]-beta-alanine；3-[benzyl-[2-(dimethylamino)ethyl]amino]propanoic acid
• CAS: 127141-10-0
• 化学式: C₁₄H₂₂N₂O₂
• 分子量: 250.341
• InChiKey: ZKYJDUHALUUJGF-UHFFFAOYSA-N

物化性质

• 沸点：
  364.1±27.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-((2-(Dimethylamino)ethyl)benzylamino)propionic acid 生成 N'-苯甲基-N,N-二甲基乙二胺 、 丙烯酸
  参考文献：
  名称：

  基于可逆共轭加成1的Cu（II）催化的未活化酯的水解

  摘要：

  当使用可移动的邻位二胺配体来增加所需的铜螯合物的稳定性时，Cu（II）催化在丙烯酸甲酯的水解中提供了16,000倍的加速。

  DOI：

  10.1016/s0040-4039(01)93395-7
• 作为产物：
  描述：

  N'-苯甲基-N,N-二甲基乙二胺 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 3-((2-(Dimethylamino)ethyl)benzylamino)propionic acid
  参考文献：
  名称：

  Metal Ion-Catalyzed Hydrolysis of Acrylate Esters and Amides by Way of Their Conjugate Addition Adducts

  摘要：

  .A formal catalytic cycle for the metal ion-catalyzed hydrolyses of acrylamide and acrylate esters is described. While various transition metal ions show little acceleration of hydrolysis reactions in free water, bringing them into proximity with esters and amides can yield increased hydrolysis rates. Such proximity effects can be brought about by covalent addition of donor atoms near the functional group. However, the simple conjugate adducts of butylmethylamine to methyl acrylate and to acrylamide did not demonstrate metal ion-catalyzed hydrolysis. Conjugate addition of a chelating amine, N-benzyl-N',N'-dimethylethylenediamine, yields adducts demonstrating significant (up to 1.5 x 10(4)-fold) hydrolysis catalysis by Cu(II) at pH 7.5 and room temperature. A model compound to test for improvement of this effect by conformational locking demonstrated no rate increase. A model compound designed to test for enhanced acceleration by two adjacent metal ions similarly showed no rate advantage as compared to the parent conjugate adduct. The conjugate reversion reaction of 3-((2-(dimethylamino)ethyl)benzylamino)propionic acid demonstrated a bell-shaped pH-rate profile with maximum rate at pH 3.

  DOI：

  10.1021/jo00127a032

文献信息

• Copper(II)-catalysed hydrolysis of an unactivated amide. Application of the groves' rule to the hydrolysis of acrylamide
  作者：Brook F. Duerr、Anthony W. Czarnik

  DOI：10.1039/c39900001707

  日期：——

  Conjugate addition of N-benzyl-N′,N′-dimethylethylenediamine to acrylamide affords a chelating amide in which the amide carbonyl can coordinate to the bound metal only via a six-membered chelate; this compound demonstrates copper(II)-catalysed amide hydrolysis, in which each metal acts on at least five equivalents of substrate.

  共轭加成的Ñ苄基N'，N'二甲基乙二胺丙烯酰胺得到的螯合酰胺，其中所述酰胺羰只能坐标到绑定金属通过一个6 -元螯合物; 该化合物证明了铜（II）催化的酰胺水解，其中每种金属作用于至少五当量的底物。
• DUERR, BROOK F.;CZARNIK, ANTHONY W., J. CHEM. SOC. CHEM. COMMUN.,(1990) N3, C. 1707-1709
  作者：DUERR, BROOK F.、CZARNIK, ANTHONY W.

  DOI：——

  日期：——
• Metal Ion-Catalyzed Hydrolysis of Acrylate Esters and Amides by Way of Their Conjugate Addition Adducts
  作者：Mark A. Mortellaro、Thomas J. Bleisch、Brook F. Duerr、Min Sok Kang、Haiyong Huang、Anthony W. Czarnik

  DOI：10.1021/jo00127a032

  日期：1995.11

  .A formal catalytic cycle for the metal ion-catalyzed hydrolyses of acrylamide and acrylate esters is described. While various transition metal ions show little acceleration of hydrolysis reactions in free water, bringing them into proximity with esters and amides can yield increased hydrolysis rates. Such proximity effects can be brought about by covalent addition of donor atoms near the functional group. However, the simple conjugate adducts of butylmethylamine to methyl acrylate and to acrylamide did not demonstrate metal ion-catalyzed hydrolysis. Conjugate addition of a chelating amine, N-benzyl-N',N'-dimethylethylenediamine, yields adducts demonstrating significant (up to 1.5 x 10(4)-fold) hydrolysis catalysis by Cu(II) at pH 7.5 and room temperature. A model compound to test for improvement of this effect by conformational locking demonstrated no rate increase. A model compound designed to test for enhanced acceleration by two adjacent metal ions similarly showed no rate advantage as compared to the parent conjugate adduct. The conjugate reversion reaction of 3-((2-(dimethylamino)ethyl)benzylamino)propionic acid demonstrated a bell-shaped pH-rate profile with maximum rate at pH 3.
• Cu(II) catalyzed hydrolysis of an unactivated ester based on reversible conjugate addition11Presented at the 197th American Chemical Society National Meeting, Dallas, TX, April 1989.
  作者：Brook F. Duerr、Anthony W. Czarnik

  DOI：10.1016/s0040-4039(01)93395-7

  日期：——

  Cu(II) catalysis provides a 16,000-fold acceleration in the hydrolysis of methyl acrylate when a removable vicinal diamine ligand is used to increase the stability of the required copper chelate.

  当使用可移动的邻位二胺配体来增加所需的铜螯合物的稳定性时，Cu（II）催化在丙烯酸甲酯的水解中提供了16,000倍的加速。