methyl 2-(N-benzylacetamido)-2-phenylacetate | 96011-42-6

• 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: methyl 2-(N-benzylacetamido)-2-phenylacetate
• 英文别名: Methyl 2-[acetyl(benzyl)amino]-2-phenylacetate
• CAS: 96011-42-6
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: OIKHVQSEOKWKST-UHFFFAOYSA-N

物化性质

• 沸点：
  188-190 °C(Press: 6 Torr)
• 密度：
  1.154±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(N-benzylacetamido)-2-phenylacetate 在 吡啶 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (2Z)-4-benzyl-5-phenyl-2-(2,2,2-trifluoroethylidene)-6-(trifluoromethyl)-1,4-oxazin-3-one
  参考文献：
  名称：

  Novel Formation and Crystal Structure of 2-(2,2,2-Trifluoroethylidene)-6-trifluoro-methyl-2,3-dihydro-4H-1,4-oxazin-3-ones from N-Acetyl-N-alkyl-a-amino Acids

  摘要：

  The title compounds (2a-g) were formed from N-acetyl-N-alkyl-alpha-amino acids (la-g) on treatment with trifluoroacetic anhydride in the presence of pyridine. The structure of the product (2a) was determined by single crystal X-Ray analysis.

  DOI：

  10.3987/com-97-7936
• 作为产物：
  描述：

  N-苄烯丁胺 在 锰 、 三氟化硼乙醚 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 20.5h， 生成 methyl 2-(N-benzylacetamido)-2-phenylacetate
  参考文献：
  名称：

  Synthesis of Arylglycines from CO₂through α-Amino Organomanganese Species

  摘要：

  In the presence of three readily available chemicals, Mn powder, BF3 center dot OEt2, and LiCl, N-acyl-N,O-acetals were successfully converted into the corresponding alpha-amino acids (arylglycine derivatives) under 1 atm of a CO2 atmosphere in high yields. The LiCl additive is necessary in order to increase the solubility and the nucleophilicity of an organomanganese intermediate. The products thus obtained were transformed into free alpha-amino acids in two steps.

  DOI：

  10.1021/ol500701n

文献信息

• Blue light-promoted N–H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates: Synthesis of unnatural α-aryl amino acid derivatives
  作者：Celso Y. Okada、Caio Y. dos Santos、Igor D. Jurberg

  DOI：10.1016/j.tet.2020.131316

  日期：2020.12

  A photochemical protocol using blue light allows the N–H insertion of amides, isatins, sulfonamides and imides into aryldiazoacetates to afford the corresponding α-amino esters. This method is experimentally simple, inexpensive and tolerates numerous functional groups, thus allowing the straightforward preparation of a variety of α-aryl amino acid derivatives in good yields.

  使用蓝光的光化学方法可以使酰胺，靛红，磺酰胺和酰亚胺的N–H插入芳基重氮乙酸酯中，得到相应的α-氨基酯。该方法在实验上是简单的，廉价的并且耐受许多官能团，因此允许以良好的产率直接制备多种α-芳基氨基酸衍生物。
• DAVTYAN, S. M.;PAPAYAN, G. L.;AKOPYAN, V. P., ARM. XIM. ZH., 1984, 37, N 11, 725-728
  作者：DAVTYAN, S. M.、PAPAYAN, G. L.、AKOPYAN, V. P.

  DOI：——

  日期：——
• Novel Formation and Crystal Structure of 2-(2,2,2-Trifluoroethylidene)-6-trifluoro-methyl-2,3-dihydro-4H-1,4-oxazin-3-ones from N-Acetyl-N-alkyl-a-amino Acids
  作者：Masami Kawase、Setsuo Saito、Hiroyuki Kikuchi、Hiroshi Miyamae

  DOI：10.3987/com-97-7936

  日期：——

  The title compounds (2a-g) were formed from N-acetyl-N-alkyl-alpha-amino acids (la-g) on treatment with trifluoroacetic anhydride in the presence of pyridine. The structure of the product (2a) was determined by single crystal X-Ray analysis.
• Synthesis of Arylglycines from CO₂through α-Amino Organomanganese Species
  作者：Tsuyoshi Mita、Jianyang Chen、Yoshihiro Sato

  DOI：10.1021/ol500701n

  日期：2014.4.18

  In the presence of three readily available chemicals, Mn powder, BF3 center dot OEt2, and LiCl, N-acyl-N,O-acetals were successfully converted into the corresponding alpha-amino acids (arylglycine derivatives) under 1 atm of a CO2 atmosphere in high yields. The LiCl additive is necessary in order to increase the solubility and the nucleophilicity of an organomanganese intermediate. The products thus obtained were transformed into free alpha-amino acids in two steps.