2-(2-methoxybenzoyl)-amino-2-methylpropionic acid | 208121-81-7

• 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: 2-(2-methoxybenzoyl)-amino-2-methylpropionic acid
• 英文别名: 2-(2-methoxybenzamido)-2-methylpropanoic acid；2-(2-methoxybenzoylamino)isobutyric acid；2-[(2-Methoxybenzoyl)amino]-2-methylpropanoic acid
• CAS: 208121-81-7
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: KXEHDQVPEOIOJU-UHFFFAOYSA-N

物化性质

• 沸点：
  445.3±30.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-methoxybenzoyl)-amino-2-methylpropionic acid 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以60.85%的产率得到N-(2-羟基苯甲酰基)-2-甲基丙氨酸
  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：

  甲氧基苯甲酰氯 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 48.0h， 生成 2-(2-methoxybenzoyl)-amino-2-methylpropionic acid
  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

文献信息

• Palladium-Catalyzed Ortho-Alkoxylation of <i>N</i>-Benzoyl α-Amino Acid Derivatives at Room Temperature
  作者：Shuangjie Li、Wei Zhu、Feng Gao、Chunpu Li、Jiang Wang、Hong Liu

  DOI：10.1021/acs.joc.6b02257

  日期：2017.1.6

  An efficient palladium-catalyzed ortho-alkoxylation of N-benzoyl α-amino acid derivatives at room temperature has been explored. This novel transformation, using amino acids as directing groups, Pd(OAc)2 as catalyst, alcohols as the alkoxylation reagents, and PhI(OAc)2 as the oxidant, showed wide generality, good functional tolerance, and high monoselectivity and regioselectivity.

  已经探索了在室温下钯的有效催化N-苯甲酰基α-氨基酸衍生物的邻烷氧基化。这种新颖的转化，以氨基酸为导向基团，以Pd（OAc）2为催化剂，以醇为烷氧基化试剂，以PhI（OAc）2为氧化剂，显示出广泛的通用性，良好的功能耐受性以及高单选择性和区域选择性。
• 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.