Methyl 2-(((2-(dimethylamino)ethyl)benzylamino)methyl-3-((2-dimethylamino)ethyl)benzylamino)propionate | 170704-79-7

• 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: Methyl 2-(((2-(dimethylamino)ethyl)benzylamino)methyl-3-((2-dimethylamino)ethyl)benzylamino)propionate
• 英文别名: Methyl 3-[benzyl-[2-(dimethylamino)ethyl]amino]-2-[[benzyl-[2-(dimethylamino)ethyl]amino]methyl]propanoate
• CAS: 170704-79-7
• 化学式: C₂₇H₄₂N₄O₂
• 分子量: 454.656
• InChiKey: MKQQKAHGJUJBTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  39.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 2-(((2-(dimethylamino)ethyl)benzylamino)methyl-3-((2-dimethylamino)ethyl)benzylamino)propionate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 36.0h， 生成 2-(((2-(Dimethylamino)ethyl)benzylamino)methyl-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
• 作为产物：
  描述：

  2-(溴甲基)丙烯酸甲酯 、 N'-苯甲基-N,N-二甲基乙二胺 以 甲醇 为溶剂， 反应 144.0h， 以54%的产率得到Methyl 2-(((2-(dimethylamino)ethyl)benzylamino)methyl-3-((2-dimethylamino)ethyl)benzylamino)propionate
  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

• 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.