methyl (R)-2-benzoylamino-2-phenylacetate

• 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: methyl (R)-2-benzoylamino-2-phenylacetate
• 英文别名: N-benzoyl-D-phenylglycine methyl ester；(R)-methyl 2-benzamido-2-phenylacetate；methyl (R)-2-benzamido-2-phenylacetate；(R)-benzamino-phenyl-acetic acid methyl ester；(R)-Benzamino-phenyl-essigsaeure-methylester；methyl (2R)-2-benzamido-2-phenylacetate
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: JSHHMLNQZWBNEE-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  在 cerium(III) chloride 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以87%的产率得到methyl (R)-2-benzoylamino-2-phenylacetate
  参考文献：
  名称：

  CeCl3·7H2O-NaI从氨基甲酸酯和酰胺中高效选择性裂解叔丁氧基羰基

  摘要：

  在环境温度和中性条件下，在乙腈中使用 CeCl 3 .7H 2 O-NaI 以高产率实现了叔丁氧基羰基的高度选择性裂解。该方法温和且与存在于基材中的多种官能团相容，例如THP、TBDMS、TBDPS、三苯甲基醚、单-BOC或Cbz保护的胺、乙酰胺、磺酰胺和苯甲酰胺等。

  DOI：

  10.1055/s-2002-20467

文献信息

• A Novel Method for Synthesizing N-Alkoxycarbonyl Aryl α-Imino Esters and Their Applications in Enantioselective Transformations
  作者：Yu Qian、Changcheng Jing、Changwei Zhai、Wen-hao Hu

  DOI：10.1002/adsc.201100615

  日期：2012.2

  A new strategy for the synthesis of N-alkoxycarbonyl aryl α-imino esters in the presence of dirhodium tetraacetate [Rh2(OAc)4] is reported to produce the desired compounds in high yield (up to 96%) under mild reaction conditions. The application of the synthetic method is demonstrated in enantioselective reduction and Friedel–Crafts reaction of indoles to afford the corresponding chiral arylglycines

  据报道，在四乙酸二ho酯[Rh 2（OAc）4 ]存在下合成N-烷氧基羰基芳基α-亚氨基酯的新策略可以在温和的反应条件下以高收率（最高达96％）产生所需的化合物。合成方法的应用在吲哚的对映选择性还原和Friedel-Crafts反应中得到了证明，分别以高收率和优异的ee提供了相应的手性芳基甘氨酸和吲哚衍生物。
• β-Isocupreidine-Catalyzed Asymmetric Baylis−Hillman Reaction of Imines
  作者：Sakie Kawahara、Ayako Nakano、Tomoyuki Esumi、Yoshiharu Iwabuchi、Susumi Hatakeyama

  DOI：10.1021/ol035102j

  日期：2003.8.1

  [reaction: see text] beta-Isocupreidine (beta-ICD)-catalyzed asymmetric Baylis-Hillman reactions of aromatic imines with 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) give (S)-enriched N-protected-alpha-methylene-beta-amino acid esters. In contrast to the corresponding aldehydes, imines show the opposite enantioselectivity. A mechanistic proposal governed by hydrogen bonding is presented.

  [反应：请参见文本]β-异cup啶（β-ICD）催化的芳香亚胺与1,1,1,3,3,3-六氟异丙基丙烯酸酯（HFIPA）的不对称Baylis-Hillman反应生成了富含（S）的N-保护的α-亚甲基-β-氨基酸酯。与相应的醛相反，亚胺显示相反的对映选择性。提出了由氢键控制的机械方案。
• Reihlen; Knoepfle, Justus Liebigs Annalen der Chemie, 1936, vol. 523, p. 199,203
  作者：Reihlen、Knoepfle

  DOI：——

  日期：——
• Chiral 1,2,4-triazoles: stereoselective acylation and chlorination
  作者：Alan R. Katritzky、Dmytro Fedoseyenko、Myong S. Kim、Peter J. Steel

  DOI：10.1016/j.tetasy.2009.12.007

  日期：2010.1

  Acyl groups are transferred from diverse N- and O-acyl derivatives of chiral 3.5-bis-(1-hydroxyethyl)-[ 1,2,4]-triazole to amino acid esters enantioselectively, with 7% to 68% ee. depending on the temperature conditions and nature of the reagents Thionyl chloride replaced the hydroxyl groups of (S)-1-[4-amino5-((S)- 1-hydroxy-ethyl)-[1,2,4]-triazol-3-yl]-ethanol 3 stereospecifically with inversion, as confirmed by X-ray analysis, which also revealed unusual crystal structures with asymmetric units comprising three molecules of 4-amino-3,5-bis(R-1-chloroethyl)-1,2,4-triazole 5 and four of 3,5-bis((R)-1-chloroethyl)-1H-1,2,4-triazole 6. (c) 2010 Elsevier Ltd All rights reserved
• Enzymic asymmetric synthesis of .alpha.-amino acids. Enantioselective cleavage of 4-substituted oxazolin-5-ones and thiazolin-5-ones
  作者：Joyce Z. Crich、Rosario Brieva、Peer Marquart、Rui Lin Gu、Steffen Flemming、Charles J. Sih

  DOI：10.1021/jo00064a010

  日期：1993.6

  A general enzymatic asymmetric synthesis of L-alpha-amino acids has been developed. This method entails the use of the Pseudomonas cepacia lipase (P-30) to catalyze the enantioselective methanolysis of a variety of 4-substituted 2-phenyloxazolin-5-one derivatives in a nonpolar organic solvent to furnish optically-active N-benzoyl-L-alpha-amino acid methyl esters (ee = 66-98%), which in turn is subjected to a protease-catalyzed kinetic resolution yielding enantiomerically-pure N-benzoyl-L-alpha-amino acids. This synergistic coupling of two enzymes allows the ready preparation of L-alpha-amino acids of high enantiopurity in yields greater than 50%, an inherent advantage over conventional resolution procedures. Two proteases were found to catalyze the enantioselective hydrolysis of a variety of 4-substituted 2-phenylthiazolin-5-one derivatives to give N-(thiobenzoyl)-L-alpha-amino acids of high optical purity.