1-(2-bromoethyl)-2-(bromomethyl)-4-methylbenzene | 112625-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-bromoethyl)-2-(bromomethyl)-4-methylbenzene
• 英文别名: 1-(2-bromo-ethyl)-2-bromomethyl-4-methyl-benzene；1-(2-Brom-aethyl)-2-brommethyl-4-methyl-benzol
• CAS: 112625-35-1
• 化学式: C₁₀H₁₂Br₂
• 分子量: 292.013
• InChiKey: KQNRSILHAVPPCX-UHFFFAOYSA-N

物化性质

• 沸点：
  143 °C(Press: 3 Torr)
• 密度：
  1.613 g/cm3(Temp: 21 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(2-bromoethyl)-2-(bromomethyl)-4-methylbenzene 在 氢溴酸 、 sodium hydride 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 20.5h， 生成 (RS)-2-amino-3-(2-(2-carboxyethyl)-5-methylphenyl)propionic acid
  参考文献：
  名称：

  A New Phenylalanine Derivative Acts as an Antagonist at the AMPA Receptor GluA2 and Introduces Partial Domain Closure: Synthesis, Resolution, Pharmacology, and Crystal Structure

  摘要：

  In order to map out molecular determinants for competitive blockade of AMPA receptor subtypes, a series of 2-carboxyethylphenylalanine derivatives has been synthesized and pharmacologically characterized in vitro. One compound in this series, (RS)-3h, showed micromolar affinity for GluA1(o). and GluA2(R)(o) receptors with an approximately 4-fold preference for GluA1/2 vs GluA3/4. In TEVC electrophysiological experiments (RS)-3h competitively antagonized GluA2(Q)(i) receptors. The X-ray structure of the active enantiomer (S)-3h in complex with GluA2-S1S2J showed a domain closure around 8 degrees. Even though the nitro and the carboxyethyl groups of (S)-3h were both anchored to Tyr702 through a water H-bond network, these interactions only induced weak subtype selectivity. In spite of the fact that (S)-3h induced a domain closure close to that observed for partial agonists, it did not produce agonist responses at GluA2 receptors under nondesensitizing conditions. 2-Carboxyethylphenylalanine derivatives provide a new synthetic scaffold for the introduction of substituents that could lead to AMPA receptor subtype-selective ligands.

  DOI：

  10.1021/jm200862h
• 作为产物：
  描述：

  7-methylisochroman 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 1-(2-bromoethyl)-2-(bromomethyl)-4-methylbenzene
  参考文献：
  名称：

  锌介导的胺与卤代烷通过汇聚配对电解进行电化学α-烷基化

  摘要：

  在此，我们报告了一种绿色且可持续的电化学策略，用于在不分开的电解条件下用卤代烷烃对叔胺进行α-烷基化。阴极的巴比尔-格氏反应产生有机锌试剂，该试剂与阳极产生的亚胺离子反应，生成 α-烷基化胺。该反应在温和的反应条件下进行，具有广泛的官能团和底物兼容性，以良好的产率提供产物。更重要的是，收敛对电解这种理想但具有挑战性的电化学技术在该反应体系中得到了有效利用。详细的机理研究表明亚胺离子中间体参与了反应过程。

  DOI：

  10.1039/d3gc01325a

文献信息

• Colonge; Boisde, Bulletin de la Societe Chimique de France, 1956, p. 1337,1342
  作者：Colonge、Boisde

  DOI：——

  日期：——
• US5364876A
  申请人：——

  公开号：US5364876A

  公开（公告）日：1994-11-15
• US5395827A
  申请人：——

  公开号：US5395827A

  公开（公告）日：1995-03-07
• [EN] omega -[2-(PHOSPHONOALKYL)PHENYL]-2-AMINOALKANOIC ACIDS AS ANTAGONISTS OF EXCITATORY AMINO ACID RECEPTORS
  申请人：NOVA PHARMACEUTICAL CORPORATION

  公开号：WO1993005772A1

  公开（公告）日：1993-04-01

  (EN) The present invention pertains to antagonists of excitatory amino acid neurotransmitter receptor antagonists, their method of preparation as well as compositions containing them which have formula (I), wherein n and m independently are 0, 1, 2, or 3; R1 is selected from the group consisting of hydrogen and R2; R2 is selected from the group consisting of hydrogen, halogen, halomethyl, nitro, amino, alkoxy, hydroxyl, hydroxymethyl, C1 to C6 lower alkyl, C7 to C12 higher alkyl, aryl and aralkyl, wherein if R2 is hydrogen, R1 is not hydrogen; R3 is selected from the group consisting of hydrogen and C1 to C6 lower alkyl; the stereoisomers thereof in their resolved or racemic form, and pharmaceutically acceptable salts thereof.(FR) La présente invention se rapporte à des antagonistes de récepteurs neuromédiateurs d'acides aminés excitateurs, à un procédé de préparation ainsi qu'à des compositions les contenant, répondant à la formule générale (I), dans laquelle n et m valent indépendamment 0, 1, 2 ou 3; R1 est choisi dans le groupe composé d'hydrogène et de R2; R2 est choisi dans le groupe comprenant hydrogène, halogène, halométhyle, nitro, amino, alcoxy, hydroxyle, hydroxyméthyle, alkyle inférieur C1 à C6, alkyle supérieur C7 à C12, aryle et aralkyle, de sorte que, si R2 représente hydrogène, R1 ne représente pas ce dernier; R3 est choisi dans le groupe comprenant hydrogène et alkyle inférieur C1 à C6. On décrit également des stéréoisomères de ces composés dans leur forme résolue ou racémique, ainsi que des sels pharmaceutiquement acceptables.
• A New Phenylalanine Derivative Acts as an Antagonist at the AMPA Receptor GluA2 and Introduces Partial Domain Closure: Synthesis, Resolution, Pharmacology, and Crystal Structure
  作者：Ewa Szymańska、Karla Frydenvang、Alberto Contreras-Sanz、Darryl S. Pickering、Elena Frola、Zorica Serafimoska、Birgitte Nielsen、Jette S. Kastrup、Tommy N. Johansen

  DOI：10.1021/jm200862h

  日期：2011.10.27

  In order to map out molecular determinants for competitive blockade of AMPA receptor subtypes, a series of 2-carboxyethylphenylalanine derivatives has been synthesized and pharmacologically characterized in vitro. One compound in this series, (RS)-3h, showed micromolar affinity for GluA1(o). and GluA2(R)(o) receptors with an approximately 4-fold preference for GluA1/2 vs GluA3/4. In TEVC electrophysiological experiments (RS)-3h competitively antagonized GluA2(Q)(i) receptors. The X-ray structure of the active enantiomer (S)-3h in complex with GluA2-S1S2J showed a domain closure around 8 degrees. Even though the nitro and the carboxyethyl groups of (S)-3h were both anchored to Tyr702 through a water H-bond network, these interactions only induced weak subtype selectivity. In spite of the fact that (S)-3h induced a domain closure close to that observed for partial agonists, it did not produce agonist responses at GluA2 receptors under nondesensitizing conditions. 2-Carboxyethylphenylalanine derivatives provide a new synthetic scaffold for the introduction of substituents that could lead to AMPA receptor subtype-selective ligands.