(2R)-N-bromoacetylphenylalanine methyl ester | 169701-40-0

• 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: (2R)-N-bromoacetylphenylalanine methyl ester
• 英文别名: N-(2-Bromoacetyl)-D-phenylalanine methyl ester；methyl (2R)-2-[(2-bromoacetyl)amino]-3-phenylpropanoate
• CAS: 169701-40-0
• 化学式: C₁₂H₁₄BrNO₃
• 分子量: 300.152
• InChiKey: QWEDTXZVZMFTIH-SNVBAGLBSA-N

物化性质

• 沸点：
  431.8±40.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  (2R)-N-bromoacetylphenylalanine methyl ester 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 methyl 3-({(3S)-3-[(3R)-3-benzyl-2,5-dioxopiperazinyl]dodecanoyl}amino)propylcarbamate
  参考文献：
  名称：

  Determination of the absolute stereochemistry of Etzionin

  摘要：

  The absolute configuration of Etzionin, a marine peptide-like compound isolated in 1989 from a red tunicate collected from the Red Sea has been determined by a combination of synthetic and spectroscopic procedures. Finally, its absolute stereochemistry has been established as 3S,3'R. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00403-8
• 作为产物：
  描述：

  D-苯丙氨酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (2R)-N-bromoacetylphenylalanine methyl ester
  参考文献：
  名称：

  Antimicrobial toxicity studies of ionic liquids leading to a ‘hit’ MRSA selective antibacterial imidazolium salt

  摘要：

  咪唑盐可分类为表面活性剂、洗涤剂、离子液体、试剂、催化剂或溶剂。对这些盐的毒性和生态毒性的研究，为其作为药物的使用以及对环境的影响提供了宝贵的信息。我们对一系列手性咪唑盐对细菌和真菌的毒性进行了筛选，包括临床病原菌株，从而鉴定出一种针对MRSA的选择性抗菌化合物。初步的结构-活性关系（SAR）信息（L-苯丙氨酸和L-缬氨酸集团所需的定位）也在这一代化合物中得以阐明。相反，大多数咪唑盐对筛选的12种真菌株和8种细菌株无毒（IC95 > 2 mM），我们提出它们是适合“绿色化学”应用的候选物质。生态毒性研究（ISO 14593生物降解“CO2顶空测试”）表明，含有L-苯丙氨酸残基的两种溴离子液体通过了测试（28天内>60%），被归类为易于生物降解。

  DOI：

  10.1039/c2gc16090k

文献信息

• Amphos-Mediated Conversion of Alkyl Azides to Diazo Compounds and One-Pot Azide-Site Selective Transient Protection, Click Conjugation, and Deprotective Transformation
  作者：Hiroki Tanimoto、Ryo Adachi、Kodai Tanisawa、Takenori Tomohiro

  DOI：10.1021/acs.orglett.4c00566

  日期：2024.3.29

  A one-pot conversion of alkyl azides to diazo compounds is outlined. After the reaction of α-azidocarbonyl compounds with Amphos, treatment of the resulting phosphazides with silica gel in a wet solvent afforded α-diazo carbonyl products. Through the azido group protection property of Amphos, inter- and intramolecular azide-site selective reactions of azido group protection, click functionalization

  概述了烷基叠氮化物向重氮化合物的一锅转化。 α-叠氮羰基化合物与Amphos反应后，在湿溶剂中用硅胶处理所得磷酰肼，得到α-重氮羰基产物。通过Amphos的叠氮基保护特性，叠氮基保护、点击官能化和重氮基脱保护的分子间和分子内叠氮位点选择性反应已被一锅展示。
• Synthesis of Xaa-Gly-Xaa′ keto-methylene tri-peptide isosteres incorporating phenylalanine, tyrosine and valine units
  作者：Barry Lygo、Carl N Rudd

  DOI：10.1016/0040-4039(95)00564-s

  日期：1995.5

  The utility of amino-acid derived beta-ketosulfones in the synthesis of keto-methylene tri-peptide isosteres Xaa-Gly-Xaa', incorporating phenylalanine, tyrosine and valine units is reported Both L,L and L,D forms of the tripeptide systems have been prepared using this methodology.
• Click-Chemistry-Derived Triazole Ligands of Arginine−Glycine−Aspartate (RGD) Integrins with a Broad Capacity To Inhibit Adhesion of Melanoma Cells and Both in Vitro and in Vivo Angiogenesis
  作者：Andrea Trabocchi、Gloria Menchi、Nicoletta Cini、Francesca Bianchini、Silvia Raspanti、Anna Bottoncetti、Alberto Pupi、Lido Calorini、Antonio Guarna

  DOI：10.1021/jm100754z

  日期：2010.10.14

  A click chemistry approach was applied for the discovery of triazole-based arginine-glycine-aspartate (RGD) mimetics by Cu(1)-catalyzed 1,3-dipolar alkyne azide coupling reaction, which showed binding all properties toward alpha(v)beta(3)/alpha(v)beta(5) integrins. Biological assays showed compound 18 capable of binding alpha(v)beta(3) integrin with nanomolar affinity according, to a two-sites model, and molecular modeling studies revealed a peculiar pi-stacking interaction between the triazole ring and Tyr178 side chain. Accordingly, compound 18 inhibited the adhesion of integrin-expressing human melanoma cells to RGD-containing proteins of the extracellular matrix, such as vitronectin, fibronectin, and osteopontin. and also angiogenesis in in vitro and in vivo experimental models. The relevant biological effects exerted by compound 18 suggest its potential application as an antiangiogenic agent in the diagnosis and therapy of tumors where alpha(v)beta(3) integrin expression is up-regulated.
• Antimicrobial toxicity studies of ionic liquids leading to a ‘hit’ MRSA selective antibacterial imidazolium salt
  作者：Deborah Coleman、Marcel Špulák、M. Teresa Garcia、Nicholas Gathergood

  DOI：10.1039/c2gc16090k

  日期：——

  Imidazolium salts can be classed as surfactants, detergents, ionic liquids, reagents, catalysts or solvents. A study of the toxicity and ecotoxicity of these salts yields valuable information for their use as pharmaceuticals as well as impact on the environment. Our approach to screen a series of chiral imidazolium salts for toxicity to bacteria and fungi, including clinical pathogen strains, has led to the identification of a ‘hit’ MRSA selective antimicrobial compound. Preliminary structure–activity-relationship (SAR) information (required position of L-phenylalanine and L-valine group) is also elucidated within this first generation of compounds. Conversely, most of the imidazolium salts were nontoxic (IC95 > 2 mM) to the 12 fungi strains and 8 bacteria strains screened, and we propose that they are suitable candidates for ‘green chemistry’ applications. Ecotoxicity studies (Biodegradation ISO 14593 ‘CO2 Headspace Test’) of two bromide ionic liquids containing L-phenylalanine residues indicate that these ionic liquids passed the test (>60% in 28 days) and classed as readily biodegradable.

  咪唑盐可分类为表面活性剂、洗涤剂、离子液体、试剂、催化剂或溶剂。对这些盐的毒性和生态毒性的研究，为其作为药物的使用以及对环境的影响提供了宝贵的信息。我们对一系列手性咪唑盐对细菌和真菌的毒性进行了筛选，包括临床病原菌株，从而鉴定出一种针对MRSA的选择性抗菌化合物。初步的结构-活性关系（SAR）信息（L-苯丙氨酸和L-缬氨酸集团所需的定位）也在这一代化合物中得以阐明。相反，大多数咪唑盐对筛选的12种真菌株和8种细菌株无毒（IC95 > 2 mM），我们提出它们是适合“绿色化学”应用的候选物质。生态毒性研究（ISO 14593生物降解“CO2顶空测试”）表明，含有L-苯丙氨酸残基的两种溴离子液体通过了测试（28天内>60%），被归类为易于生物降解。
• Determination of the absolute stereochemistry of Etzionin
  作者：Esther Vaz、Miryam Fernandez-Suarez、Luis Muñoz

  DOI：10.1016/s0957-4166(03)00403-8

  日期：2003.7

  The absolute configuration of Etzionin, a marine peptide-like compound isolated in 1989 from a red tunicate collected from the Red Sea has been determined by a combination of synthetic and spectroscopic procedures. Finally, its absolute stereochemistry has been established as 3S,3'R. (C) 2003 Elsevier Science Ltd. All rights reserved.