(S)-甲基-2-溴-3-羟基丙酸甲酯 | 7691-28-3

• 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
• 中文名称: (S)-甲基-2-溴-3-羟基丙酸甲酯
• 中文别名: 甲基-2-溴-3-羟基丙酸甲酯；2-溴-3-羟基丙酸甲酯
• 英文名称: methyl 2-bromo-3-hydroxypropanoate
• 英文别名: methyl 2-bromo-3-hydroxypropionate
• CAS: 7691-28-3
• 化学式: C₄H₇BrO₃
• 分子量: 183.002
• InChiKey: GVXAFLUDYYQGCG-UHFFFAOYSA-N

物化性质

• 沸点：
  245℃
• 密度：
  1.677
• 闪点：
  102℃

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2918199090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存储条件为2-8°C，并需保存在惰性气体中。

反应信息

• 作为反应物：
  描述：

  (S)-甲基-2-溴-3-羟基丙酸甲酯 在 sodium hydroxide 作用下， 生成 2-bromo-3-hydroxypropionic acid
  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：

  2-bromo-3-hydroxypropionic acid 在 氢溴酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-甲基-2-溴-3-羟基丙酸甲酯
  参考文献：
  名称：

  SYNTHESIS OF INIMERS AND HYPERBRANCHED POLYMERS

  摘要：

  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。

  公开号：

  US20110046334A1

文献信息

• Reaction of N-Haloamide. XX. Bromo-formyloxylation of α, β-Unsaturated Esters with N, N-Dibromobenzenesulfonamide and Formic Acid
  作者：YOSHIO UENO、AKEMI YAMASAKI、HIROMI TERAUCHI、SHOJI TAKEMURA

  DOI：10.1248/cpb.22.1646

  日期：——

  α, β-Unsaturated esters were made to react with N, N-dibromobenzenesulfonamide and formic acid in chloroform to give bromo-formyloxyesters. Methyl acrylate (1a), ethyl crotonate (2a), ethyl trans-cinnamate (3a), methyl tiglate (4a), methyl methacrylate (5a), and methyl phenylacrylate (6a) gave methyl 2-bromo-3-formyloxypropionate (1b), ethyl erythro-2-bromo-3-formyloxybutyrate (2b), ethyl erythro-2-bromo-3-formyloxy-3-phenylpropionate (3b), methyl erythro-2-bromo-3-formyloxy-2-methylbutyrate (4b), a mixture of methyl 3-bromo-2-formyloxy-2-methylpropionate (5b) and methyl 2-bromo-3-formyloxy-2-methylpropionate (5c), and methyl 3-bromo-2-formyloxy-2-phenylpropionate (6b) respectively in good yields.

  α, β-不饱和酯与N, N-二溴苯磺酰胺和甲酸在氯仿中反应，生成溴代甲酰氧基酯。甲基丙烯酸酯（1a）、乙基巴豆酸酯（2a）、乙基反式肉桂酸酯（3a）、甲基惕格酸酯（4a）、甲基甲基丙烯酸酯（5a）和甲基苯基丙烯酸酯（6a）分别以良好的产率生成甲基2-溴-3-甲酰氧基丙酸酯（1b）、乙基erythro-2-溴-3-甲酰氧基丁酸酯（2b）、乙基erythro-2-溴-3-甲酰氧基-3-苯基丙酸酯（3b）、甲基erythro-2-溴-3-甲酰氧基-2-甲基丁酸酯（4b）、甲基3-溴-2-甲酰氧基-2-甲基丙酸酯（5b）和甲基2-溴-3-甲酰氧基-2-甲基丙酸酯（5c）的混合物以及甲基3-溴-2-甲酰氧基-2-苯基丙酸酯（6b）。
• Photochemical α-carboxyalkylation of tryptophols and tryptamines <i>via</i> C–H functionalization
  作者：Zhiqiang Pan、Yuchang Liu、Fengchi Hu、Qinglong Liu、Wenbin Shang、Chengfeng Xia

  DOI：10.1039/d0cc00847h

  日期：——

  strategy activated the C-Br bonds of α-bromo-alkylcarboxylic esters to provide carbon-centered radicals under the catalysis of Ir(iii) photocatalyst and coupled with indole derivatives. This methodology displayed wide functional group tolerance and excellent regioselectivity, and was applied to the late-stage functionalization and preparation of indole-containing hybrids.

  已经开发了在可见光照射下通过CH键的官能化使色酚和色胺的α-羧烷基化的方法。该光化学策略在Ir（iii）光催化剂的催化下并与吲哚衍生物偶联，活化了α-溴代烷基羧酸酯的C-Br键以提供以碳为中心的自由基。该方法显示出宽泛的官能团耐受性和优异的区域选择性，并应用于后期功能化和含吲哚杂种的制备。
• [EN] COMPOUNDS ACTIVE TOWARDS NUCLEAR RECEPTORS<br/>[FR] COMPOSÉS ACTIFS VIS-À-VIS DES RÉCEPTEURS NUCLÉAIRES
  申请人：NUEVOLUTION AS

  公开号：WO2021124279A1

  公开（公告）日：2021-06-24

  Disclosed are compounds active towards nuclear receptors, pharmaceutical compositions containing the compounds and use of the compounds in therapy.

  揭示了对核受体活性的化合物，包含这些化合物的药物组合物以及这些化合物在治疗中的用途。
• [EN] PHENYLIMIDE-CONTAINING BENZOTHIAZOLE DERIVATIVE OR ITS SALT AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME<br/>[FR] DÉRIVÉ DE BENZOTHIAZOLE CONTENANT PHÉNYLIMIDE OU SON SEL ET COMPOSITION PHARMACEUTIQUE LE COMPRENANT
  申请人：YUHAN CORP

  公开号：WO2013043001A1

  公开（公告）日：2013-03-28

  The present invention provides a phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt, a process for the preparation thereof, and a pharmaceutical composition comprising the same. The phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt can selectively inhibit the protein-protein interaction between KRS and a laminin receptor (LR), thereby inhibiting migration of cancer cells. Therefore, the phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt may be usefully applied for preventing or treating the diseases associated with cancer cell metastasis.

  本发明提供了一种含有苯甲酰亚胺基的苯并噻唑衍生物或其药用可接受盐，以及其制备方法和包含其的药物组合物。所述含有苯甲酰亚胺基的苯并噻唑衍生物或其药用可接受盐可以选择性地抑制KRS和层粘连蛋白受体（LR）之间的蛋白质相互作用，从而抑制癌细胞的迁移。因此，含有苯甲酰亚胺基的苯并噻唑衍生物或其药用可接受盐可能被有益地应用于预防或治疗与癌细胞转移相关的疾病。
• 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。