N-(methoxycarbonyl)methyl-L-phenylalanine methyl ester | 77328-29-1

• 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: N-(methoxycarbonyl)methyl-L-phenylalanine methyl ester
• 英文别名: methyl N-methoxycarbonylmethyl-L-phenylalaninate；methyl (2S)-2-[(2-methoxy-2-oxoethyl)amino]-3-phenylpropanoate
• CAS: 77328-29-1
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: YMIHOVLXRGYTHJ-NSHDSACASA-N

物化性质

• 沸点：
  182 °C(Press: 10 Torr)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(methoxycarbonyl)methyl-L-phenylalanine methyl ester 在 盐酸 作用下， 反应 17.0h， 以90%的产率得到N-carboxymethyl-L-phenylalanine
  参考文献：
  名称：

  异常氨基酸及其肽的研究。十二. N-（羧甲基）氨基酸的化学。I. N-（羧甲基）氨基酸及其酯的制备、性质和表征

  摘要：

  N-羧甲基(Cm-)氨基酸及其单酯和二酯通过多种途径制备，并与母体氨基酸及其酯的物理和手性特性进行了比较。对相应氨基酸和溴乙酸制备游离Cm-氨基酸的分离步骤进行了改进；目标化合物也通过二苄基酯的催化氢解获得。Cm-氨基酸的单烷基酯的异构体对同样可通过苄基烷基酯获得。证明二酯适用于 Cm-氨基酸的 GLC 和 MS 分析。所有游离的 Cm-L-氨基酸及其 N-乙硫代碳硫酰衍生物的二环己基铵盐在 CD 测量中分别在 200-225 nm 和 335-350 nm 处显示出正 Cotton 效应；

  DOI：

  10.1246/bcsj.53.2555
• 作为产物：
  描述：

  L-苯丙氨酸 在 氯化亚砜 作用下， 反应 8.0h， 生成 N-(methoxycarbonyl)methyl-L-phenylalanine methyl ester
  参考文献：
  名称：

  异常氨基酸及其肽的研究。十二. N-（羧甲基）氨基酸的化学。I. N-（羧甲基）氨基酸及其酯的制备、性质和表征

  摘要：

  N-羧甲基(Cm-)氨基酸及其单酯和二酯通过多种途径制备，并与母体氨基酸及其酯的物理和手性特性进行了比较。对相应氨基酸和溴乙酸制备游离Cm-氨基酸的分离步骤进行了改进；目标化合物也通过二苄基酯的催化氢解获得。Cm-氨基酸的单烷基酯的异构体对同样可通过苄基烷基酯获得。证明二酯适用于 Cm-氨基酸的 GLC 和 MS 分析。所有游离的 Cm-L-氨基酸及其 N-乙硫代碳硫酰衍生物的二环己基铵盐在 CD 测量中分别在 200-225 nm 和 335-350 nm 处显示出正 Cotton 效应；

  DOI：

  10.1246/bcsj.53.2555

文献信息

• LiOH-mediated N-monoalkylation of α-amino acid esters and a dipeptide ester using activated alkyl bromides
  作者：Jong Hyun Cho、B.Moon Kim

  DOI：10.1016/s0040-4039(01)02394-2

  日期：2002.2

  Selective N-monoalkylation of α-amino esters with activated alkyl bromides was studied using various alkali or alkali earth metal bases. In the production of N-monoalkylated amino ester derivatives and suppression of N,N-dialkylation, lithium hydroxide was more effective than any other alkali or alkali earth bases examined. Using this protocol, a variety of N-alkylated α-amino esters and even dipeptide

  使用各种碱金属或碱土金属碱，研究了用活化的烷基溴对α-氨基酯的选择性N-单烷基化。在N-单烷基化氨基酯衍生物的生产和N，N-二烷基化的抑制中，氢氧化锂比任何其他所检查的碱金属或碱土金属碱更有效。使用该方案，已经使用各种活化的烷基溴成功地制备了各种N-烷基化的α-氨基酯，甚至二肽酯。
• A convenient synthesis of chiral dioxocyclens and application as chiral solvating agents
  作者：Quan Yuan、Enqin Fu、Xiaojun Wu、Maohai Fang、Peng Xue、Chengtai Wu、Jiahua Chen

  DOI：10.1016/s0040-4039(02)00623-8

  日期：2002.5

  This paper report. a very short and efficient synthesis of chiral dioxocyclens starting, from natural amino acids. NMR experiments undertaken to assess the chiral recognition properties of these chiral macrocycles. The NMR spectra of mandelic acid or its derivatives in the presence and absence of the chiral dioxocyclens showed that these macrocycles have different enantiomeric discriminating ability, It was revealed that this type of dioxocyclen may be promising hosts Cor chiral discrimination. (C) 2002 Elsevier Science Ltd. All rights reserved.
• The Synthesis of New Chiral Dioxocyclens
  作者：Quan Yuan、Peng Xue、Maohai Fang、Enqin Fu、Chengtai Wu

  DOI：10.1081/scc-120020204

  日期：2003.6

  This article reports a short and efficient synthesis of chiral dioxocyclens starting from natural amino acids. Four new chiral dioxocyclens that contain different substituents at the chiral center were obtained. These dioxocyclens could not only be used for chiral recognition, but provide a feasible way for the synthesis of chiral cyclens.
• Synthesis and chiral recognition of novel chiral fluorescence receptors bearing 9-anthryl moieties
  作者：Kuo-Xi Xu、Xiao-Jun Wu、Yong-Bing He、Shun-Ying Liu、Guang-Yan Qing、Ling-Zhi Meng

  DOI：10.1016/j.tetasy.2004.12.023

  日期：2005.2

  Two chiral fluorescence receptors 1 and 2 have been synthesized, and their structures characterized by IR, H-1 NMR, MS spectra and elemental analysis. The chiral recognition of the receptors was studied by 1H NMR and fluorescence spectra. The results demonstrate that the receptors and tetrabutyl ammonium mandelate formed a 1:1 complex. Two receptors exhibit good chiral recognition abilities towards the enantiomers of tetrabutylammonium mandelate. (C) 2005 Elsevier Ltd. All rights reserved.
• Studies of Unusual Amino Acids and Their Peptides. XII. The Chemistry of<i>N</i>-(Carboxymethyl)amino Acids. I. The Preparation, Properties, and Characterization of<i>N</i>-(Carboxymethyl)amino Acids and Their Esters
  作者：Toshifumi Miyazawa

  DOI：10.1246/bcsj.53.2555

  日期：1980.9

  N-Carboxymethyl(Cm-)amino acids and their mono- and diesters were prepared by several routes, and their physical and chiroptical properties were compared with those of the parent amino acids and their esters. The isolation procedure was improved for the preparation of the free Cm-amino acids obtained from the corresponding amino acids and bromoacetic acid; the aimed-at compounds were also obtained

  N-羧甲基(Cm-)氨基酸及其单酯和二酯通过多种途径制备，并与母体氨基酸及其酯的物理和手性特性进行了比较。对相应氨基酸和溴乙酸制备游离Cm-氨基酸的分离步骤进行了改进；目标化合物也通过二苄基酯的催化氢解获得。Cm-氨基酸的单烷基酯的异构体对同样可通过苄基烷基酯获得。证明二酯适用于 Cm-氨基酸的 GLC 和 MS 分析。所有游离的 Cm-L-氨基酸及其 N-乙硫代碳硫酰衍生物的二环己基铵盐在 CD 测量中分别在 200-225 nm 和 335-350 nm 处显示出正 Cotton 效应；