1-(溴甲基)-3-氯-2-甲基苯 | 90369-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(溴甲基)-3-氯-2-甲基苯
• 中文别名: 4-溴-3-氟苯乙酸
• 英文名称: 1-(bromomethyl)-3-chloro-2-methylbenzene
• CAS: 90369-76-9
• 化学式: C₈H₈BrCl
• 分子量: 219.509
• InChiKey: ORGIHYDPMFXTEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1-(溴甲基)-3-氯-2-甲基苯 在 magnesium 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 30.0h， 生成 1,2-bis(3'-cyano-2'-methylphenyl)ethane
  参考文献：
  名称：

  Synthesis, Reactions, and Structural and NMR Features of [2.2]Metacyclophane Monoenes and Their Tricarbonylchromium and Cyclopentadienyliron(+) Complexes

  摘要：

  8,16-Dimethyl-, 5,8,13,16-tetramethyl, and 4,6,8,12,14,16-hexamethyl[2,2]metacyclophanene have been synthesized from the corresponding methyl-substituted 3-thia[3.2]metacyclophane precursors via a Wittig rearrangement-Hofmann elimination procedure. Simple addition of bromine or similar electrophiles to the bridge double bond of the cyclophane monoenes did not occur; rather, the methyl-substituted dihydropyrenes were formed. However, mono- and bis-tricarbonylchromium and monocyclopentadienyliron complexes were obtained using ligand-exchange reactions. Addition of bromine to the cyclophane bridge double bond of the iron complex did occur, but unusually slowly. Surprisingly, debromination rather than dehydrobromination occurred when the dibromo addition product was treated with a variety of bases. Photoisomerization of the monoenes and nucleophilic substitution of the metal complexes was also investigated. The geometries of the monoenes and their complexes were compared to the cyclophanes and the cyclophanedienes and to the monothia- and dithiacyclophanes, by comparison of X-ray and calculated structural data and NMR spectroscopic data. Introduction of double bonds into the cyclophane bridges causes the cyclophane step to be less steep but increases distortion of the internal atoms out of the plane of the benzene rings. Making the bridges nonidentical also causes a sideways twist of the step.

  DOI：

  10.1021/jo990721k
• 作为产物：
  描述：

  3-氯-2-甲基苯甲腈 在 吡啶 、 sodium tetrahydroborate 、 三溴化磷 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 8.5h， 生成 1-(溴甲基)-3-氯-2-甲基苯
  参考文献：
  名称：

  Syntheses and reactions of the first dithia[3.1.3.1]metacyclophanes, [2.1.2.1]metacyclophanes, and [2.1.2.1]metacyclophanedienes

  摘要：

  DOI：

  10.1021/jo00188a004

文献信息

• Benzimidazole Boronic Acid Derivatives As PI3 Kinase Inhibitors
  申请人：GlaxoSmithKline LLC

  公开号：US20130157977A1

  公开（公告）日：2013-06-20

  This invention relates to the use of benzimidazole boronic acid derivatives for the modulation, notably the inhibition of the activity or function of the phosphoinositide 3′ OH kinase family (hereinafter PI3 kinases), suitably, PI3Kα, PI3Kδ, PI3Kβ, and/or PI3Kγ. Suitably, the present invention relates to the use of benzimidazole boronic acids in the treatment of one or more disease states selected from: autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, allergy, asthma, pancreatitis, multiorgan failure, kidney diseases, platelet aggregation, cancer, sperm motility, transplantation rejection, graft rejection and lung injuries. More suitably, the present invention relates to PI3Kβ selective benzimidazole boronic acid compounds for treating cancer.

  这项发明涉及苯并咪唑硼酸衍生物用于调节磷脂酰肌醇3′ OH激酶家族（以下简称PI3激酶）的活性或功能，特别是抑制其活性。适当地，PI3Kα、PI3Kδ、PI3Kβ和/或PI3Kγ。适当地，本发明涉及苯并咪唑硼酸在治疗以下一种或多种疾病状态中的应用：自身免疫性疾病、炎症性疾病、心血管疾病、神经退行性疾病、过敏、哮喘、胰腺炎、多器官功能衰竭、肾脏疾病、血小板聚集、癌症、精子活动力、移植排斥、移植排斥和肺部损伤。更适当地，本发明涉及PI3Kβ选择性苯并咪唑硼酸化合物用于治疗癌症。
• [EN] THIAZOLOPYRIMIDINONE DERIVATIVES AS PI3 KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE THIAZOLOPYRIMIDINONE COMME INHIBITEURS DE LA KINASE PI3
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2010135504A1

  公开（公告）日：2010-11-25

  This invention relates to the use of thiazolopyrimidinone derivatives for the modulation, notably the inhibition of the activity or function of the phosphoinositide 3' OH kinase family (hereinafter PI3 kinases), suitably, PI3Kα, PI3Kδ, PI3Kβ, and/or PI3Kγ. Suitably, the present invention relates to the use of thiazolopyrimidinones in the treatment of one or more disease states selected from: autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, allergy, asthma, pancreatitis, multiorgan failure, kidney diseases, platelet aggregation, cancer, sperm motility, transplantation rejection, graft rejection and lung injuries. More suitably, the present invention relates to PI3Kβ selective thiazolopyrimidinones compounds for treating cancer.

  这项发明涉及噻唑吡咯嘧啶酮衍生物在调节磷脂酰肌醇3' OH激酶家族（以下简称PI3激酶）的活性或功能，特别是抑制其活性或功能方面的用途，适当地，PI3Kα、PI3Kδ、PI3Kβ和/或PI3Kγ。适当地，本发明涉及噻唑吡咯嘧啶酮在治疗以下一种或多种疾病状态中的用途：自身免疫性疾病、炎症性疾病、心血管疾病、神经退行性疾病、过敏、哮喘、胰腺炎、多器官功能衰竭、肾脏疾病、血小板聚集、癌症、精子活动力、移植排斥、移植物排斥和肺部损伤。更适当地，本发明涉及PI3Kβ选择性噻唑吡咯嘧啶酮化合物用于治疗癌症。
• BENZIMIDAZOLE DERIVATIVES AS PI3 KINASE INHIBITORS
  申请人：Qu Junya

  公开号：US20120088767A1

  公开（公告）日：2012-04-12

  This invention relates to the use of benzimidazole derivatives for the modulation, notably the inhibition of the activity or function of the phosphoinositide 3′ OH kinase family (hereinafter PI3 kinases), suitably, PI3Kα, PI3Kβ, PI3Kβ, and/or PI3Kγ. Suitably, the present invention relates to the use of benzimidazoles in the treatment of one or more disease states selected from: autoimmune disorders, inflammatory diseases, cardiovascular diseases, neurodegenerative diseases, allergy, asthma, pancreatitis, multiorgan failure, kidney diseases, platelet aggregation, cancer, sperm motility, transplantation rejection, graft rejection and lung injuries. More suitably, the present invention relates to PI3Kβ selective benzimidazoles compounds for treating cancer.

  这项发明涉及苯并咪唑衍生物在调节磷脂酰肌醇3′ OH激酶家族（以下简称PI3激酶）的活性或功能，特别是抑制其活性或功能方面的用途。适当地，本发明涉及苯并咪唑在治疗以下一种或多种疾病状态中的用途：自身免疫性疾病、炎症性疾病、心血管疾病、神经退行性疾病、过敏、哮喘、胰腺炎、多器官功能衰竭、肾脏疾病、血小板聚集、癌症、精子活动力、移植排斥、移植物排斥和肺部损伤。更适当地，本发明涉及选择性作用于PI3Kβ的苯并咪唑化合物用于治疗癌症。
• Enantioselective Intermolecular C–H Amination Directed by a Chiral Cation
  作者：Alexander Fanourakis、Benjamin D. Williams、Kieran J. Paterson、Robert J. Phipps

  DOI：10.1021/jacs.1c05206

  日期：2021.7.14

  The enantioselective amination of C(sp3)–H bonds is a powerful synthetic transformation yet highly challenging to achieve in an intermolecular sense. We have developed a family of anionic variants of the best-in-class catalyst for Rh-catalyzed C–H amination, Rh2(esp)2, with which we have associated chiral cations derived from quaternized cinchona alkaloids. These ion-paired catalysts enable high levels

  C( sp 3 )-H 键的对映选择性胺化是一种强大的合成转化，但在分子间意义上实现却极具挑战性。我们开发了一系列用于 Rh 催化的 C–H 胺化的一流催化剂的阴离子变体，Rh 2 (esp) 2，我们将衍生自季铵化金鸡纳生物碱的手性阳离子与它们相关联。这些离子对催化剂能够在带有侧羟基的底物的苄基 C-H 胺化中实现高水平的对映选择性。此外，手性阳离子的喹啉似乎与铑络合物进行轴向连接，与 Rh 2 (esp) 2相比，提供了更高的产物产率并突出阳离子所发挥的双重作用。这些结果强调了使用手性阳离子在具有挑战性的过渡金属催化转化中控制对映选择性的潜力。
• [EN] IMIDAZOPYRIDAZINE DERIVATIVES AS ΡΙ3Κβ INHIBITORS<br/>[FR] DÉRIVÉS D'IMIDAZOPYRIDAZINE UTILISÉS EN TANT QU'INHIBITEURS DE PΙ3ΚΒ
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2016097347A1

  公开（公告）日：2016-06-23

  The present invention relates to substituted imidazopyridazine derivatives of Formula (I) wherein the variables have the meaning defined in the claims. The compounds according to the present invention are useful as pΙ3Κβ inhibitors. The invention further relates to processes for preparing such novel compounds, pharmaceutical compositions comprising said compounds as an active ingredient as well as the use of said compounds as a medicament.

  本发明涉及式（I）的取代咪唑吡啶嗪衍生物，其中变量的含义如索赔中所定义。根据本发明的化合物可用作pΙ3Κβ抑制剂。本发明还涉及制备这种新颖化合物的方法，包含该化合物作为活性成分的药物组合物，以及将该化合物用作药物的用途。