2-(3-bromo-5-methylphenyl)acetonitrile | 871116-91-5

• 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: 2-(3-bromo-5-methylphenyl)acetonitrile
• CAS: 871116-91-5
• 化学式: C₉H₈BrN
• 分子量: 210.073
• InChiKey: ACTDHAVSXUXSGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-bromo-5-methylphenyl)acetonitrile 在 硫酸 作用下， 以13.51 g的产率得到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
• 作为产物：
  描述：

  3,5-二甲基溴苯 在 N-溴代丁二酰亚胺(NBS) 、 四丁基氟化铵 、 过氧化苯甲酰 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 2-(3-bromo-5-methylphenyl)acetonitrile
  参考文献：
  名称：

  [EN] COMPOUNDS THAT MEDIATE PROTEIN DEGRADATION AND METHODS OF USE THEREOF
  [FR] COMPOSÉS ASSURANT LA MÉDIATION DE LA DÉGRADATION DE PROTÉINES ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  Described herein, in part, are compounds that bind to and modulate the surface of cereblon and mediate the degradation of GSPT1, and are therefore useful in the treatment of various disorders, such as cancer.

  公开号：

  WO2023069731A1

文献信息

• Novel HIV reverse transcriptase inhibitors
  申请人：Guo Hongyan

  公开号：US20080070920A1

  公开（公告）日：2008-03-20

  The invention is related to compounds of Formula (I), (II), or (III): or a pharmaceutically acceptable salt, solvate, ester, and/or phosphonate thereof, compositions containing such compounds, and therapeutic methods that include the administration of such compounds.

  这项发明涉及到以下化合物的公式(I)、(II)或(III)： 或其药用可接受的盐、溶剂化合物、酯和/或膦酸酯，含有这种化合物的组合物，以及包括给予这种化合物的治疗方法。
• PROCESSES FOR PREPARING HIV REVERSE TRANSCRIPTASE INHIBITORS
  申请人：Guo Hongyan

  公开号：US20090163712A1

  公开（公告）日：2009-06-25

  Compounds of Formula (I): can be prepared by a multi-step process from compounds of Formula (II): wherein G is Cl, Br or I.

  公式（I）的化合物可以通过多步骤过程从公式（II）的化合物制备而成： 其中G是Cl、Br或I。
• [EN] PYRIMIDONE DERIVATIVES AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF A VIRAL DISEASE<br/>[FR] DÉRIVÉS PYRIMIDONE ET LEUR UTILISATION DANS LE TRAITEMENT, LE SOULAGEMENT OU LA PRÉVENTION D'UNE MALADIE VIRALE
  申请人：SAVIRA PHARMACEUTICALS GMBH

  公开号：WO2017109088A1

  公开（公告）日：2017-06-29

  The present invention relates to a compound having the general formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, codrug, cocrystal, prodrug, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, (I) which are useful in treating, ameloriating or preventing a viral disease, in particular influenza.

  本发明涉及具有通式（I）的化合物，可选地以药学上可接受的盐、溶剂合物、多型体、共药、共晶、前药、互变异构体、外消旋体、对映体或二对映体或其混合物的形式存在，（I）对治疗、改善或预防病毒性疾病，特别是流感具有用处。
• Dual aromatase–sulfatase inhibitors based on the anastrozole template: synthesis, in vitro SAR, molecular modelling and in vivo activity
  作者：Toby Jackson、L. W. Lawrence Woo、Melanie N. Trusselle、Surinder K. Chander、Atul Purohit、Michael J. Reed、Barry V. L. Potter

  DOI：10.1039/b707768h

  日期：——

  crucial for enzyme inhibition, was modified to include a phenol sulfamate ester motif, the pharmacophore for potent irreversible steroid sulfatase inhibition. Adaption of a synthetic route to Anastrozole was accomplished via selective radical bromination and substitution reactions to furnish a series of inhibitory aromatase pharmacophores. Linking these fragments to the phenol sulfamate ester moiety employed

  描述了一系列新型双重芳香酶-硫酸酯酶抑制剂（DASIs）的合成和生物学评估。假定双重抑制芳香酶和类固醇硫酸酯酶，两者都负责雌激素的生物合成，在治疗激素依赖性乳腺癌中将是有益的。这些化合物基于阿那曲唑芳香化酶抑制剂模板，该模板在维持血红素连接三唑部分对酶抑制至关重要的同时，经过修饰，使其包括苯酚氨基磺酸酯基序，即有效抑制不可逆类固醇硫酸酯酶的药效基团。通过选择性自由基溴化和取代反应以提供一系列抑制性芳香化酶药效基团，可以使合成路线适应阿那曲唑。将这些片段连接至氨基磺酸氨基酚酯部分，使用S（N）2，Heck和Mitsunobu反应与酚类前体进行反应，从中通过氨磺酰化反应完成DASI。在体外，先导化合物11对芳香化酶（IC（50）3.5 nM）具有很高的效力，与阿那曲唑（IC（50）1.5 nM）相当，而对甾族硫酸酯酶的活性却中等。然而，在体内，11出人意料地表现出有效的双重抑制作用。将化合物1
• [EN] PYRIMIDONE DERIVATIVES AND THEIR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF A VIRAL DISEASE<br/>[FR] DÉRIVÉS DE PYRIMIDONE ET LEUR UTILISATION DANS LE TRAITEMENT, LE SOULAGEMENT OU LA PRÉVENTION D'UNE MALADIE VIRALE
  申请人：SAVIRA PHARMACEUTICALS GMBH

  公开号：WO2017158151A1

  公开（公告）日：2017-09-21

  The present invention relates to a compound having the general formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, codrug, cocrystal, prodrug, tautomer, racemate, enantiomer, or diastereomer or mixture thereof, which are useful in treating, ameloriating or preventing a viral disease, in particular influenza.

  本发明涉及具有通式（I）的化合物，可选地为药学上可接受的盐、溶剂合物、多晶形、共药、共晶体、前药、互变异构体、消旋体、对映体或二对映体或其混合物，用于治疗、改善或预防病毒性疾病，特别是流感。