(R)-N-benzoylalanine methyl ester | 7260-27-7

• 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: (R)-N-benzoylalanine methyl ester
• 英文别名: N-benzoylalanine methyl ester；N-benzoyl-D-alanine methyl ester；methyl (2R)-2-benzamidopropanoate
• CAS: 7260-27-7
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: QRDFLIILGVFYCF-MRVPVSSYSA-N

物化性质

• 熔点：
  56-58 °C
• 沸点：
  383.3±25.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (R)-N-benzoylalanine methyl ester 在 二叔丁基过氧化物 作用下， 以 叔丁醇 为溶剂， 生成 methyl 2-benzamido-2-methylpropanoate 、 Aspartic acid, N-benzoyl-3-(benzoylamino)-2,3-dimethyl-, dimethylester, (2R,3R)-rel-
  参考文献：
  名称：

  Selective reaction of glycine residues in hydrogen atom transfer from amino acid derivatives

  摘要：

  DOI：

  10.1021/ja00185a039
• 作为产物：
  描述：

  (3R,6R)-N-Benzoyl-3,6-dihydro-3-methyl-2H-1,2-oxazin-6-carbonsaeure-ethylester 在 amalgiertes Aluminium 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 (R)-N-benzoylalanine methyl ester
  参考文献：
  名称：

  Braun, Heinz; Felber, Helena; Kresze, Guenter, Liebigs Annalen der Chemie, 1993, # 3, p. 261 - 268

  摘要：

  DOI：

文献信息

• Asymmetric electrochemical oxidation of 1,2-diols, aminoalcohols, and aminoaldehydes in the presence of chiral copper catalyst
  作者：Daishirou Minato、Hitomi Arimoto、Yoko Nagasue、Yosuke Demizu、Osamu Onomura

  DOI：10.1016/j.tet.2008.05.015

  日期：2008.7

  Asymmetric oxidation of 1,2-diols, aminoalcohols, and aminoaldehydes in the presence of copper(II) triflate and (R,R)-Ph-BOX was accomplished by electrochemical method using Br− as a mediator. This oxidation was applicable to kinetic resolution of racemic cis-cycloalkane-1,2-diols, aminoalcohols, and aminoaldehydes to afford optically active compounds with good to high enantioselectivity.

  在铜的存在下的1,2-二醇，氨基醇，氨基醛和不对称氧化（II），三氟甲磺酸和（- [R ，- [R）-Ph-BOX通过使用溴电化学方法来实现-作为介体。该氧化适用于外消旋的顺式-环烷烃-1，2-二醇，氨基醇和氨基醛的动力学拆分，以提供具有良好至高对映选择性的旋光化合物。
• 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.
• Dynamic Kinetic Resolutions Catalyzed by a Planar-Chiral Derivative of DMAP:  Enantioselective Synthesis of Protected α-Amino Acids from Racemic Azlactones
  作者：Jack Liang、J. Craig Ruble、Gregory C. Fu

  DOI：10.1021/jo9803380

  日期：1998.5.1
• Effecient Kinetic Resolution of Racemic Amino Aldehydes by Oxidation with<i>N</i>-Iodosuccinimide
  作者：Daishirou Minato、Yoko Nagasue、Yosuke Demizu、Osamu Onomura

  DOI：10.1002/anie.200804188

  日期：2008.11.24
• Asymmetric synthesis of uncommon α-amino acids by diastereoselective alkylations of a chiral glycine equivalent
  作者：Kiyoshi Tanaka、Mija Ahn、Yukari Watanabe、Kaoru Fuji

  DOI：10.1016/0957-4166(96)00212-1

  日期：1996.6

  For the purpose of practical preparations of a variety of enantiomerically pure uncommon alpha-amino acids, alkylations of the chiral glycine equivalent 5, which possesses axially chiral binaphthol as an auxiliary, with several electrophiles were investigated. The alkylation proceeded smoothly in satisfactory chemical yield with high diastereoselectivities to give protected alpha-amino acid derivatives. The free hydroxyl group of the auxiliary played an important role for the induction of diastereoselectivity. Using (S)-1,1'-binaphthalene-2,2'-diol as a chiral auxiliary, D-alpha-amino acid derivatives having the unnatural (R)-configuration were predominantly obtained. Some of the alkylated products were converted into free non-proteinogenic D-alpha-amino acids. Copyright (C) 1996 Elsevier Science Ltd