methyl 2-pentanamido-2-phenylacetate

• 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-pentanamido-2-phenylacetate
• 英文别名: Methyl 2-(pentanoylamino)-2-phenylacetate
• 化学式: C₁₄H₁₉NO₃
• mdl: MFCD17442137
• 分子量: 249.31
• InChiKey: AIKFBZKTCZGHSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-pentanamido-2-phenylacetate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 N-pentanoyl phenylglycine
  参考文献：
  名称：

  Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

  摘要：

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.

  DOI：

  10.1021/jacs.5b10524
• 作为产物：
  描述：

  methyl 2-((diphenylmethylene)amino)-2-phenylacetate 在 盐酸 、 三乙胺 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 methyl 2-pentanamido-2-phenylacetate
  参考文献：
  名称：

  Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

  摘要：

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.

  DOI：

  10.1021/jacs.5b10524

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。
• Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and <i>N</i>,<i>O</i>-Acetal Derivatives
  作者：Tianli Wang、Zhaoyuan Yu、Ding Long Hoon、Claire Yan Phee、Yu Lan、Yixin Lu

  DOI：10.1021/jacs.5b10524

  日期：2016.1.13

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.