3-Brom-5-methylphenylessigsaeure | 51719-66-5

• 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: 3-Brom-5-methylphenylessigsaeure
• 英文别名: 3-bromo-5-methylphenylacetic acid；(3-Bromo-5-methylphenyl)acetic acid；2-(3-bromo-5-methylphenyl)acetic acid
• CAS: 51719-66-5
• 化学式: C₉H₉BrO₂
• 分子量: 229.073
• InChiKey: CLTIMCXGBQJJIQ-UHFFFAOYSA-N

物化性质

• 沸点：
  339.3±27.0 °C(Predicted)
• 密度：
  1.533±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Brom-5-methylphenylessigsaeure 在 aluminum (III) chloride 、 氯化亚砜 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Regioisomerism in the Synthesis of a Chiral Aminotetralin Drug Compound: Unraveling Mechanistic Details and Diastereomer-Specific In-Depth NMR Investigations

  摘要：

  During chemical process development of a novel 2-aminotetralin derivative intended for use as an antidepressant, scrutiny of the byproduct present in the drug molecule revealed a set of regioisomers. Detailed studies showed that this impurity issue originated from an early synthetic step in which a brominated tetralone motif was generated in a ring-closing protocol. It was found that this reaction was accompanied by a migration of the aromatic bromo substituent via different bromonium species along two discrete pathways. This example of the halogen dance reaction resulted in the formation of a series of tetralone impurities with a bromine distributed across all available aromatic positions of the tetralin nucleus. Subsequently, when subjected to reductive amination conditions, each of these tetralones gave rise to pairs of aminotetralins in a diastereomeric relationship. NMR investigations revealed that the alicyclic portion of the compounds thus formed displayed very complex signal patterns, which required further in-depth studies using a variety of sophisticated techniques. As a result, a deep insight into the structural features of the current 2-aminotetralin family was obtained, which is emphasized by the definition of a novel "0.2 ppm rule" allowing the absolute configuration at tetralin C-2 to be determined.

  DOI：

  10.1021/jo300277y
• 作为产物：
  描述：

  1-溴-3-(溴甲基)-5-甲基苯 在 硫酸 作用下， 以 乙醇 、 水 为溶剂， 生成 3-Brom-5-methylphenylessigsaeure
  参考文献：
  名称：

  Regioisomerism in the Synthesis of a Chiral Aminotetralin Drug Compound: Unraveling Mechanistic Details and Diastereomer-Specific In-Depth NMR Investigations

  摘要：

  During chemical process development of a novel 2-aminotetralin derivative intended for use as an antidepressant, scrutiny of the byproduct present in the drug molecule revealed a set of regioisomers. Detailed studies showed that this impurity issue originated from an early synthetic step in which a brominated tetralone motif was generated in a ring-closing protocol. It was found that this reaction was accompanied by a migration of the aromatic bromo substituent via different bromonium species along two discrete pathways. This example of the halogen dance reaction resulted in the formation of a series of tetralone impurities with a bromine distributed across all available aromatic positions of the tetralin nucleus. Subsequently, when subjected to reductive amination conditions, each of these tetralones gave rise to pairs of aminotetralins in a diastereomeric relationship. NMR investigations revealed that the alicyclic portion of the compounds thus formed displayed very complex signal patterns, which required further in-depth studies using a variety of sophisticated techniques. As a result, a deep insight into the structural features of the current 2-aminotetralin family was obtained, which is emphasized by the definition of a novel "0.2 ppm rule" allowing the absolute configuration at tetralin C-2 to be determined.

  DOI：

  10.1021/jo300277y

文献信息

• SPIRO IMIDOZOLE DERIVATIVES AS PPAR MODULATORS
  申请人：Epple Robert

  公开号：US20090137610A1

  公开（公告）日：2009-05-28

  The invention provides compounds (Ia), (Ib) and (Ic), pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of the Peroxisome Proliferator-Activated Receptor (PPAR) families.

  本发明提供了化合物(Ia)、(Ib)和(Ic)，包括此类化合物的制药组合物以及使用这些化合物治疗或预防与过氧化物酶体增殖物激活受体（PPAR）家族活性相关的疾病或障碍的方法。
• [EN] COMPOUNDS, COMPOSITIONS AND METHODS OF TREATING CANCER<br/>[FR] COMPOSÉS, COMPOSITIONS ET MÉTHODES DE TRAITEMENT DU CANCER
  申请人：HOTSPOT THERAPEUTICS INC

  公开号：WO2022221704A1

  公开（公告）日：2022-10-20

  The present disclose includes, among other things, compounds that treat or lessen the severity of cancer, pharmaceutical compositions and methods of making and using the same.

  本公开涉及的内容包括用于治疗或减轻癌症严重程度的化合物、制药组合物以及制备和使用这些化合物的方法。
• WO2007/87448
  申请人：——

  公开号：——

  公开（公告）日：——
• SPIRO IMIDAZOLE DERIVATIVES AS PPAR MODULATORS
  申请人：IRM LLC

  公开号：EP1979355A1

  公开（公告）日：2008-10-15
• [EN] SPIRO IMIDAZOLE DERIVATIVES AS PPAR MODULATORS<br/>[FR] DÉRIVÉS D'IMADAZOLE SPIRO UTILISÉS COMME MODULATEURS DU RÉCEPTEUR PPAR
  申请人：IRM LLC

  公开号：WO2007087448A1

  公开（公告）日：2007-08-02

  [EN] The invention provides compounds (Ia), (Ib) and (Ic), pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of the Peroxisome Proliferator-Activated Receptor (PPAR) families.
  [FR] La présente invention concerne des composés (Ia), (ib) et (Ic), des compositions pharmaceutiques comprenant ces composés et des procédés d'utilisation de ces composés destinés à traiter ou prévenir des maladies ou des troubles associés à l'activité des familles du récepteur activé par les proliférateurs de peroxisome (PPAR).