(2S)-amino-3-phenyl-propionic acid pentyl ester | 81686-33-1

• 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: (2S)-amino-3-phenyl-propionic acid pentyl ester
• 英文别名: phenylalanine pentyl ester；pentyl (2S)-2-amino-3-phenylpropanoate
• CAS: 81686-33-1
• 化学式: C₁₄H₂₁NO₂
• mdl: MFCD13330543
• 分子量: 235.326
• InChiKey: VOOOGYQBISWQHH-ZDUSSCGKSA-N

物化性质

• 沸点：
  330.5±22.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  戊醇 、 (2S)-amino-3-phenyl-propionic acid pentyl ester 在 磷酸二苯酯 、 1-hydroxytetraphenyl-cyclopentadienyl(tetraphenyl-2,4-cyclopentadien-1-one)-μ-hydrotetracarbonyldiruthenium(II) 作用下， 以 甲苯 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  使用具有高立体化学保留的醇直接催化 α-氨基酸酯和酰胺的 N-烷基化

  摘要：

  天然丰富的手性支架（例如α-氨基酸酯或酰胺）与广泛丰富的醇的直接官能化，无需任何外消旋作用，是一个要求很高的转化，对于生物活性化合物的合成至关重要。本文开发了一种稳健且通用的方法，用于 α-氨基酸酯和酰胺与醇的直接N-烷基化。这种强大的钌催化方法是原子经济的、无碱的，并且可以很好地保留立体化学完整性。使用磷酸二苯酯作为添加剂对于显着提高反应活性和产物选择性至关重要。值得注意的是，唯一的副产品是水，两种底物都可能来自可再生资源。

  DOI：

  10.1002/cssc.202100373
• 作为产物：
  描述：

  戊醇 、 L-苯丙氨酸 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以86%的产率得到(2S)-amino-3-phenyl-propionic acid pentyl ester
  参考文献：
  名称：

  New amino acid-based anionic surfactants and their use as enantiodiscriminating lyotropic liquid crystalline NMR solvents

  摘要：

  New amino acid-based anionic surfactants have been synthesized and their use as chiral oriented NMR solvents studied. A series of sulfonated amphiphilic L-Phe or L-Ala derivatives with pentyl to tetradecyl tails were prepared by reacting the corresponding amino acid esters with o-sulfobenzoic anhydride. Their critical micelle concentrations (CMCs) range from 1.6 x 10(-5) to 1.4 x 10(-2) mol/L and depend on the alkyl chain length as well as on the nature of the amino acid block. These values are comparatively lower than those of classical surfactants such as alkylbenzenesulfonates and N-acylamino-acid carboxylates. Their use as chiral liquid crystals (CLC) for analytical purposes is reported. In particular, it is shown that aqueous solutions of these chiral sulfonates in the presence of chlorinated solvents (CHCl3, CH2Cl2, C2H2Cl4, or CCl4) provide homogeneous oriented NMR solvents able to differentiate between enantiomers of D,L-alanine-2-d(1) using proton and deuterium NMR spectroscopy. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.01.022

文献信息

• [EN] NOVEL PRODRUGS OF NUCLEOSIDE PHOSPHONATES<br/>[FR] NOUVEAUX PROMÉDICAMENTS DE PHOSPHONATES NUCLÉOSIDIQUES
  申请人：UNIV LEUVEN KATH

  公开号：WO2018172416A1

  公开（公告）日：2018-09-27

  The present invention relates to novel phosphonoamidate prodrugs. The invention also relates to the use of these novel phosphonate-modified nucleosides to treat or prevent viral infections and their use to manufacture a medicine to treat or prevent viral infections, particularly infections with viruses such as the herpes simplex virus 1, herpes simplex virus 2, human cytomegalovirus, varicella zoster virus, vaccinia virus and adenovirus.

  本发明涉及新型磷酸酰胺前药。本发明还涉及使用这些新型磷酸酯修饰核苷酸来治疗或预防病毒感染以及它们用于制造用于治疗或预防病毒感染的药物，特别是用于疱疹病毒1型、疱疹病毒2型、人类巨细胞病毒、水痘带状疱疹病毒、牛痘病毒和腺病毒等病毒感染。
• [EN] COMPOUNDS, COMPOSITIONS AND USE THEREOF<br/>[FR] COMPOSÉS, COMPOSITIONS ET UTILISATION DE CEUX-CI
  申请人：ILLUSTRIS PHARMACEUTICALS INC

  公开号：WO2018152428A1

  公开（公告）日：2018-08-23

  This application relates to compounds prepared from cosmetically acceptable ingredients, methods of preparation thereof, and use thereof. Compounds are of formula (I) U-C-B, or salts thereof, wherein U, C and B are moieties of cosmetically acceptable ingredients U', C' and B'. In living tissues, the compounds can release at least one of U', C' and B'. The bond between C and U and/or between C and B is labile in living tissues. In particular, the compounds comprise moieties derived from salicylic acid, retinol and retinoic acid or nicotinic acid.

  本申请涉及由化妆品可接受成分制备的化合物，其制备方法以及其使用。化合物的公式为（I）U-C-B，或其盐，其中U，C和B是化妆品可接受成分U'，C'和B'的基团。在活体组织中，化合物可以释放U'，C'和B'中的至少一种。C和U之间和/或C和B之间的键在活体组织中是不稳定的。特别地，该化合物包括从水杨酸、视黄醇和视黄酸或烟酸中导出的基团。
• In vivo incorporation of unnatural amino acids
  申请人：Schultz Peter

  公开号：US20070117184A1

  公开（公告）日：2007-05-24

  The invention provides methods and compositions for in vivo incorporation of unnatural amino acids. Also provided are compositions including proteins with unnatural amino acids.

  本发明提供了体内合成非天然氨基酸的方法和组合物。还提供了包括非天然氨基酸蛋白质的组合物。
• METHOD FOR PREPARING PHENYLALANINE DERIVATIVES HAVING QUINAZOLINE-DIONE SKELETON AND INTERMEDIATES FOR USE IN THE PREPARATION OF DERIVATIVES
  申请人：KATAOKA Noriyasu

  公开号：US20090318688A1

  公开（公告）日：2009-12-24

  A method for preparing a phenylalanine derivative having a quinazoline-dione ring represented by the following formula (1) or a pharmaceutically acceptable salt thereof, comprising the following steps (a), (b) and (c): (a) reacting an acyl phenylalanine derivative represented by the following formula (2): with a carbonyl group-introducing reagent and a specific anthranilic acid derivative to thus form the corresponding carboxy-asymmetric urea derivative; (b) converting the carboxy-asymmetric urea derivative into the corresponding quinazoline-dione derivative in the presence of a carboxyl group-activating agent: (c) if desired, substituting an N-alkyl group for the hydrogen atom bonded to the nitrogen atom present in the quinazoline-dione ring of the quinazoline-dione derivative using an N-alkylation agent and then deprotecting the resulting product, when the substituent R3′ which is a group corresponding to R3 is protected. According to this method, there can be obtained a phenylalanine derivative having a quinazoline-dione skeleton in a industrially favorably high yield.

  一种制备具有喹唑啉二酮环的苯丙氨酸衍生物或其药学上可接受的盐的方法，其由以下步骤(a)、(b)和(c)组成：(a)用羰基基团引入试剂和特定的蒽酸衍生物反应，以形成相应的羧基-不对称脲衍生物，所述脲衍生物由以下式(2)所表示的酰基苯丙氨酸衍生物反应而成：(b)在羧基活化剂的存在下，将羧基-不对称脲衍生物转化为相应的喹唑啉二酮衍生物；(c)如果需要，在R3'是被保护的基团对应的R3时，使用N-烷基化试剂将取代喹唑啉二酮环中氮原子上的氢原子的N-烷基基团替换，并去保护所得产物。根据该方法，可以得到一个工业上有利的高产率的具有喹唑啉二酮骨架的苯丙氨酸衍生物。
• METHOD FOR PREPARING PHENYLALANINE DERIVATIVES HAVING QUINAZOLINE-DIONE SKELETON AND INTERMEDIATES FOR USE IN THE PREPARATION OF THE DERIVATIVES
  申请人：KATAOKA Noriyasu

  公开号：US20110313154A1

  公开（公告）日：2011-12-22

  A method for preparing a phenylalanine derivative having a quinazoline-dione ring represented by the following formula (1) or a pharmaceutically acceptable salt thereof, comprising the following steps (a), (b) and (c): (a) reacting an acyl phenylalanine derivative represented by the following formula (2): with a carbonyl group-introducing reagent and a specific anthranilic acid derivative to thus form the corresponding carboxy-asymmetric urea derivative; (b) converting the carboxy-asymmetric urea derivative into the corresponding quinazoline-dione derivative in the presence of a carboxyl group-activating agent: (c) if desired, substituting an N-alkyl group for the hydrogen atom bonded to the nitrogen atom present in the quinazoline-dione ring of the quinazoline-dione derivative using an N-alkylation agent and then deprotecting the resulting product, when the substituent R3′ which is a group corresponding to R3 is protected. According to this method, there can be obtained a phenylalanine derivative having a quinazoline-dione skeleton in a industrially favorably high yield.

  一种制备具有喹唑啉二酮环的苯丙氨酸衍生物或其药学上可接受的盐的方法，其表示为以下公式（1），包括以下步骤（a）、（b）和（c）： （a）将以下公式（2）所表示的酰基苯丙氨酸衍生物与羰基引入试剂和特定的蒽酰氨基酸衍生物反应，从而形成相应的羧基不对称脲衍生物； （b）在羧基活化剂的存在下，将羧基不对称脲衍生物转化为相应的喹唑啉二酮衍生物； （c）如果需要，当保护基R3'对应于R3的基团受保护时，使用N-烷基化试剂将连接在喹唑啉二酮环中氮原子上的氢原子取代为N-烷基基团，然后去保护所得产物。通过该方法，可以在工业上获得具有喹唑啉二酮骨架的苯丙氨酸衍生物，且收率高。