2-bromo-3-hydroxypropionic acid | 160732-12-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-bromo-3-hydroxypropionic acid
• 英文别名: 2-bromo-3-hydroxypropanoic acid
• CAS: 160732-12-7
• 化学式: C₃H₅BrO₃
• 分子量: 168.975
• InChiKey: OIODSHQRJGRDLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-3-hydroxypropionic acid 在 ammonium hydroxide 作用下， 反应 12.0h， 生成 DL-丝氨酸
  参考文献：
  名称：

  Structure-Function Relationship of Acyl Amino Acid Surfactants: Surface Activity and Antimicrobial Properties

  摘要：

  Amino acid surfactants (AAS), having the general structure alpha-amino-(N-acyl)-beta-alkoxypropionate, were synthesized chemically. Surface activity and antimicrobial properties of the AAS were evaluated. Increases in acyl chain length (i.e., C-10-C-14) resulted in a linear reduction in surface tension (i.e., 43-36 mN . m(-1)), as well as dramatic decreases in critical micelle concentrations (cmc) (i.e., 17.9-0.43 mM). Strong correlations existed between the cmc of AAS and their minimal inhibitory concentrations (mic) against Escherichia coli, Pseudomonas aeruginosa, Aspergillus niger, and Saccharomyces cerevisiae. Sensitivity of the microorganisms to the various AAS followed the order Staphylococcus aureus > A. niger = S. cerevisiae > E. coli > P. aeruginosa. In comparison with methyl p-hydroxybenzoate, AAS (MN14) showed 2-8, 64, and 4-8 times the activity against Gram-negative bacteria, Gram-positive bacteria, and fungi, respectively. Surface adsorption and/or bifunctional binding to the cell membrane may account for AAS action on microorganisms.

  DOI：

  10.1021/jf00052a004
• 作为产物：
  描述：

  L-丝氨酸 在 氢溴酸 、 potassium bromide 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 14.0h， 以90%的产率得到2-bromo-3-hydroxypropionic acid
  参考文献：
  名称：

  酸化缩水甘油分子缩略词

  摘要：

  从半经验轨道计算中已经提出了由氨和胺引起的缩水甘油酸打开反应的模型。它提供了一种评估传入的亲核试剂与环氧乙烷取代基之间不同相互作用的方法。交错构象（顺式取代）中羧酸盐的立体和库仑相互作用对合理化实验区域选择性具有重大影响。

  DOI：

  10.1016/s0040-4020(01)85509-5

文献信息

• [EN] DERMAL COMPOSITIONS CONTAINING UNNATURAL HYGROSCOPIC AMINO ACIDS<br/>[FR] COMPOSITIONS DERMATOLOGIQUES CONTENANT DES AMINOACIDES HYGROSCOPIQUES NON NATURELS
  申请人：MEDPHARM LTD

  公开号：WO2014072747A1

  公开（公告）日：2014-05-15

  Unnatural, hygroscopic amino acids are useful to enhance the moisture retention and uptake properties of skin. In particular, such amino acids are N-hydroxyserine, N- hydroxyglycine, L-homoserine,alpha-hydroxyglycine, 2-(aminooxy) -2-hydroxyacetic acid, 2-hydroxy-2-(hydroxyamino) acetic acid, 2- (aininooxy)acetic acid, and combinations thereof.

  不自然的、亲水性的氨基酸对增强皮肤的保湿和吸湿性能是有用的。特别是，这些氨基酸包括N-羟基丝氨酸、N-羟基甘氨酸、L-同丝氨酸、α-羟基甘氨酸、2-(氨氧基)-2-羟基乙酸、2-羟基-2-(羟氨基)乙酸、2-(氨氧基)乙酸，以及它们的组合。
• SYNTHESIS OF HYPERBRANCHED POLYMETHACRYLATES AND POLYACRYLATES BY A HALOINIMER APPROACH
  申请人：Pugh Coleen

  公开号：US20200055995A1

  公开（公告）日：2020-02-20

  A new synthetic pathway for hyperbranched polyacrylates and polymethacrylates including the steps of preparing an inimer and polymerizing the inimer to form hyperbranched polymers or copolymers.

  一种新的合成途径，用于制备高支化聚丙烯酸酯和聚甲基丙烯酸酯，包括准备一种初始单体并聚合该初始单体以形成高支化聚合物或共聚物。
• Cobalt‐Catalyzed 1,4‐Aryl Migration/Desulfonylation Cascade: Synthesis of α‐Aryl Amides
  作者：Nicolas Gillaizeau‐Simonian、Etienne Barde、Amandine Guérinot、Janine Cossy

  DOI：10.1002/chem.202005129

  日期：2021.2.24

  A cobalt‐catalyzed 1,4‐aryl migration/disulfonylation cascade applied to α‐bromo N‐sulfonyl amides was developed. The reaction was highly chemoselective, allowing the preparation of α‐aryl amides possessing a variety of functional groups. The method was used as the key step to synthesize an alkaloid, (±)‐deoxyeseroline. Mechanistic investigations suggest a radical process.

  开发了应用于α-溴代N-磺酰基酰胺的钴催化的1,4-芳基迁移/二磺酰化级联反应。该反应具有高度的化学选择性，可以制备具有各种官能团的α-芳基酰胺。该方法被用作合成生物碱（±）-脱氧羟脯氨酸的关键步骤。机械研究表明这是一个激进的过程。
• SYNTHESIS OF INIMERS AND HYPERBRANCHED POLYMERS
  申请人：Pugh Coleen R.

  公开号：US20110046334A1

  公开（公告）日：2011-02-24

  An inimer, and process for making same, having the following formula: wherein X=halogen, nitroxide, thioester; R═H or CH 3 ; and R′=aliphatic, non-aliphatic, linear or branched, mesogenic, non mesogenic, chiral, achiral, hydrocarbon, non-hydrocarbon, selected from fluorocarbon, oligo(oxyethylene) and siloxane substituents, alkyl, aryl, mesogenic group, non-mesogenic group, aliphatic, non-aliphatic, siloxane , perfluoroalkyl, perfluoroaryl, or other fluorocarbon group, and polymers, and the process of making them, from the inimer.

  一种含有以下配方的Inimer及其制备方法： 其中X=卤素、亚硝基、硫酯；R=H或CH3；R′=脂肪族、非脂肪族、直链或支链、向列型、非向列型、手性、非手性、碳氢化合物、非碳氢化合物，选自氟碳、寡聚（氧乙烯）和硅氧烷取代基、烷基、芳基、向列基团、非向列基团、脂肪族、非脂肪族、硅氧烷、全氟烷基、全氟芳基或其他氟碳基团、以及聚合物，以及从Inimer制备它们的方法。
• Design and Regioselective Synthesis of (2-Bromo-2-alkoxycarbonyl)ethyl Acrylates as Inimers for Hyperbranched (Co)Polyacrylates
  作者：Coleen Pugh、Bindu Raveendra、Anirudha Singh、Reichel Samuel、Guillermina Garcia

  DOI：10.1055/s-0030-1258497

  日期：2010.8

  A route based on deaminohalogenation of serine is established to synthesize bromoinimers that can be homopolymerized to produce hyperbranched polyacrylates that are true architectural analogues of linear polyacrylates; that is, an ester group is attached to every other carbon along the polymer backbone, and each repeat unit contains a free ester side chain.

  基于丝氨酸脱氨卤化的路线被建立用于合成可均聚形成高度支化的聚丙烯酸酯的溴代亚胺，这些聚丙烯酸酯是线性聚丙烯酸酯的真实结构类似物；即，聚合物主链上每隔一个碳原子连接一个酯基，并且每个重复单元包含一个自由的酯侧链。