N-苯甲酰基-N,2-二甲基丙氨酸 | 409108-28-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苯甲酰基-N,2-二甲基丙氨酸
• 英文名称: N-benzoyl-N-methyl-α-amino-2-methylpropionic acid
• 英文别名: N-benzoyl-α-amino-2-methylpropionic acid；α-(benzoyl-methyl-amino)-isobutyric acid；α-(Benzoyl-methyl-amino)-isobuttersaeure；2-[Benzoyl(methyl)amino]-2-methylpropanoic acid
• CAS: 409108-28-7
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: GIDOYAZOBQQMAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  malachite 、 N-苯甲酰基-N,2-二甲基丙氨酸 、 水 以 水 、 异丙醇 为溶剂， 以56.82%的产率得到[Cu(μ(2)-O2CC(CH3)2NHCOC6H5)2]*0.5H2O
  参考文献：
  名称：

  Structural and mechanistic studies of the copper(II)-assisted ortho-hydroxylation of benzoates by trimethylamine N-oxide

  摘要：

  N-benzoyl-2-methylalanine (H2L1) is ortho-hydroxylated stereoselectively by trimethylamine N-oxide (TMAO) in the presence of copper(II). The experimental structure of [Cu(L-1)(TMAO)(2)] suggests that the oxygen transfer agent TMAO transfers the oxygen atom to copper(II), and (L-1)(2-), coordinated to copper(II) by a carboxylate oxygen and the amide nitrogen donor, is well pre-organized for an oxygen transfer from copper to the ortho carbon atom of the benzene ring. Product analyses as a function of reaction time of the copper(II)-mediated ortho-hydroxylation reaction with H2L1 and various derivatives support the suggestion of a reactive copper-oxo or copper-hydroxo intermediate, stabilized by a five-membered chelate with hard carboxylate and N-amide donors. The analysis also suggests that there is a pre-equilibrium with a Cu:L = 1:1 ratio, and this might involve Cu/L2-/TMAO or dicopper complexes. Depending on the ligand H2L, complexation with the salicylate product may inhibit the ortho-hydroxylation reaction. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(01)01291-8
• 作为产物：
  描述：

  2-(甲基氨基)-2-甲基丙腈 在 硫酸 、 水 、 potassium carbonate 作用下， 生成 N-苯甲酰基-N,2-二甲基丙氨酸
  参考文献：
  名称：

  Gabriel, Chemische Berichte, 1914, vol. 47, p. 2924

  摘要：

  DOI：

文献信息

• Gabriel, Chemische Berichte, 1913, vol. 46, p. 1355
  作者：Gabriel

  DOI：——

  日期：——
• Gabriel, Chemische Berichte, 1914, vol. 47, p. 2924
  作者：Gabriel

  DOI：——

  日期：——
• Structural and mechanistic studies of the copper(II)-assisted ortho-hydroxylation of benzoates by trimethylamine N-oxide
  作者：Wim Buijs、Peter Comba、Danny Corneli、Hans Pritzkow

  DOI：10.1016/s0022-328x(01)01291-8

  日期：2002.1

  N-benzoyl-2-methylalanine (H2L1) is ortho-hydroxylated stereoselectively by trimethylamine N-oxide (TMAO) in the presence of copper(II). The experimental structure of [Cu(L-1)(TMAO)(2)] suggests that the oxygen transfer agent TMAO transfers the oxygen atom to copper(II), and (L-1)(2-), coordinated to copper(II) by a carboxylate oxygen and the amide nitrogen donor, is well pre-organized for an oxygen transfer from copper to the ortho carbon atom of the benzene ring. Product analyses as a function of reaction time of the copper(II)-mediated ortho-hydroxylation reaction with H2L1 and various derivatives support the suggestion of a reactive copper-oxo or copper-hydroxo intermediate, stabilized by a five-membered chelate with hard carboxylate and N-amide donors. The analysis also suggests that there is a pre-equilibrium with a Cu:L = 1:1 ratio, and this might involve Cu/L2-/TMAO or dicopper complexes. Depending on the ligand H2L, complexation with the salicylate product may inhibit the ortho-hydroxylation reaction. (C) 2002 Elsevier Science B.V. All rights reserved.