(S)-ethyl 2-benzamido-2-phenylacetate | 7554-21-4

• 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: (S)-ethyl 2-benzamido-2-phenylacetate
• 英文别名: (S)-Benzoylamino-phenyl-acetic acid ethyl ester；ethyl (2S)-2-benzamido-2-phenylacetate
• CAS: 7554-21-4
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: GYEKVSOESPZWDI-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙基(2S)-氨基(苯基)乙酸酯 、 苯甲醇 在 碘苯二乙酸 、 N-羟基丁二酰亚胺 作用下， 以 乙腈 为溶剂， 反应 0.42h， 以88%的产率得到(S)-ethyl 2-benzamido-2-phenylacetate
  参考文献：
  名称：

  N-羟基琥珀酰亚胺/苯碘二乙酸酯介导的苯甲醇与氨基酸酯的氧化酰胺化

  摘要：

  摘要提出了一个简单的协议，涉及苯甲醇与氨基酸酯的无金属氧化酰胺化。与传统的金属介导的二氢挤出不同，酰胺化以自由基途径进行。该方法在无金属条件、不昂贵的商业起始底物方面是有利的。起始材料中的各种取代基也是可以容忍的，位阻氨基酸侧链可以提供良好的酰胺产物产率。图形概要

  DOI：

  10.1080/00397911.2017.1281960

文献信息

• Self-association-free dimeric cinchona alkaloid organocatalysts: unprecedented catalytic activity, enantioselectivity and catalyst recyclability in dynamic kinetic resolution of racemic azlactones
  作者：Ji Woong Lee、Tae Hi Ryu、Joong Suk Oh、Han Yong Bae、Hyeong Bin Jang、Choong Eui Song

  DOI：10.1039/b917882a

  日期：——

  Self-association-free, bifunctional, squaramide-based dimeric cinchona alkaloid organocatalysts show unprecedented catalytic activity, enantioselectivity and catalyst recyclability in the dynamic kinetic resolution (DKR) reaction of a broad range of racemic azlactones.

  无自缔合，双官能，基于方胺的二聚体金鸡纳生物碱有机催化剂在广泛的外消旋a内酯的动态动力学拆分（DKR）反应中显示出空前的催化活性，对映选择性和催化剂可回收性。
• Brønsted Acid Catalyzed Dynamic Kinetic Resolution of Azlactones for the Synthesis of Aryl Glycine Derivatives
  作者：Liu-Zhu Gong、Chao Wang、Hong-Wen Luo

  DOI：10.1055/s-0030-1259711

  日期：2011.4

  The dynamic kinetic resolution of C4-aryl azlactones with alcohols was investigated by employing Brønsted acid catalysis. The reaction provided an efficient complementary approach to access chiral aryl glycine derivatives with excellent yields (up to 99%) and enantioselectivities (up to 96% ee).

  通过采用布朗斯特酸催化，研究了C4-芳基阿兹拉克通与醇的动态动力学分离。该反应提供了一种有效的互补方法，以高产率（高达99%）和优异的对映选择性（高达96% ee）获得手性芳基甘氨酸衍生物。
• Synthesis of Amides and Peptides by Employing [4-(Acetylamino) phenyl]imidodisulfuryl Difluoride (AISF) as a Coupling Reagent
  作者：Swetha Bharamawadeyar、Eti Chetankumar、Chinthaginjala Srinivasulu、Vommina V. Sureshbabu

  DOI：10.1055/s-0043-1763675

  日期：2024.5

  A new synthetic approach for the preparation of amides and peptides containing amino acids as well as aryl acids and amines by employing [4-(acetylamino)phenyl]imidodisulfuryl difluoride (AISF) as a carboxylic acid activator under mild conditions is delineated. The use of AISF as an acid activator allows the reaction to be performed efficiently. This operationally simple amidation is amenable to a
• Oxidative amidation of benzyl alcohols with amino acid esters mediated by <i>N</i>-hydroxysuccinimide/phenyliodine diacetate
  作者：Mandipogula Mahesh、Veladi Panduranga、Girish Prabhu、Roopesh Kumar L、P. Venkata Ramana、Vommina V. Sureshbabu

  DOI：10.1080/00397911.2017.1281960

  日期：2017.4.3

  amidation of benzyl alcohols with amino acid esters has been presented. The amidation proceeds in a radical pathway unlike in conventional metal-mediated extrusion of dihydrogen. The method is advantageous in terms of metal-free conditions, nonexpensive commercial starting substrates. Also various substituents in the starting materials are tolerated and sterically hindered amino acid side chains could

  摘要提出了一个简单的协议，涉及苯甲醇与氨基酸酯的无金属氧化酰胺化。与传统的金属介导的二氢挤出不同，酰胺化以自由基途径进行。该方法在无金属条件、不昂贵的商业起始底物方面是有利的。起始材料中的各种取代基也是可以容忍的，位阻氨基酸侧链可以提供良好的酰胺产物产率。图形概要