1-bromo-2-(bromomethyl)-4-chloro-5-(4-ethylbenzyl)benzene | 1061315-44-3

• 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-bromo-2-(bromomethyl)-4-chloro-5-(4-ethylbenzyl)benzene
• 英文别名: 1-bromo-2-(bromomethyl)-4-chloro-5-[(4-ethylphenyl)methyl]benzene
• CAS: 1061315-44-3
• 化学式: C₁₆H₁₅Br₂Cl
• 分子量: 402.556
• InChiKey: LBYJIZUOGFCGRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• 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

反应信息

• 作为反应物：
  描述：

  1-bromo-2-(bromomethyl)-4-chloro-5-(4-ethylbenzyl)benzene 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以86%的产率得到[2-溴-5-氯-4-(4-乙基苄基)苯基]甲醇
  参考文献：
  名称：

  A new and improved process for C-aryl glucoside SGLT2 inhibitors

  摘要：

  A practical and scalable synthesis of C-glycosides identified as highly potent sodium-dependent glucose transporter 2 (SGLT2) inhibitors is described. Highlights of the synthetic process are a concise, ten-step synthesis of a structurally complex active pharmaceutical ingredient from a known intermediate via a selective and quantitative addition of an aryl species to the Weinreb amide, and the isomers of undesired ortho-products were avoided during the preparation. The chemistry developed has been applied to prepare SGLT2 inhibitors without recourse to chromatography.

  DOI：

  10.1007/s00706-015-1458-z
• 作为产物：
  描述：

  5-bromo-4-(bromomethyl)-2-chloro-N-methoxy-N-methylbenzamide 在 三乙基硅烷 、 三氟甲磺酸 、 magnesium 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,2-二溴乙烷 为溶剂， 反应 15.0h， 生成 1-bromo-2-(bromomethyl)-4-chloro-5-(4-ethylbenzyl)benzene
  参考文献：
  名称：

  A new and improved process for C-aryl glucoside SGLT2 inhibitors

  摘要：

  A practical and scalable synthesis of C-glycosides identified as highly potent sodium-dependent glucose transporter 2 (SGLT2) inhibitors is described. Highlights of the synthetic process are a concise, ten-step synthesis of a structurally complex active pharmaceutical ingredient from a known intermediate via a selective and quantitative addition of an aryl species to the Weinreb amide, and the isomers of undesired ortho-products were avoided during the preparation. The chemistry developed has been applied to prepare SGLT2 inhibitors without recourse to chromatography.

  DOI：

  10.1007/s00706-015-1458-z

文献信息

• BENZYLIC GLYCOSIDE DERIVATIVES AND METHODS OF USE
  申请人：Chen Yuanwei

  公开号：US20080242596A1

  公开（公告）日：2008-10-02

  Provided are compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The invention also provides pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions which are affected by SGLT inhibition.

  提供了具有对钠依赖性葡萄糖共转运蛋白SGLT具有抑制作用的化合物。该发明还提供了药物组合物、制备这些化合物的方法、合成中间体以及使用这些化合物的方法，独立或与其他治疗剂结合，用于治疗受SGLT抑制影响的疾病和病况。
• Benzylic glycoside derivatives and methods of use
  申请人：Theracos, Inc.

  公开号：US07838498B2

  公开（公告）日：2010-11-23

  Provided are compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The invention also provides pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions which are affected by SGLT inhibition.

  提供了对钠依赖性葡萄糖共转运体SGLT具有抑制作用的化合物。本发明还提供了制备这些化合物的药物组合物、方法、合成中间体以及使用这些化合物的方法，单独或与其他治疗剂联合治疗受SGLT抑制影响的疾病和病症。
• EP2064222B1
  申请人：——

  公开号：EP2064222B1

  公开（公告）日：2014-05-07
• US7838498B2
  申请人：——

  公开号：US7838498B2

  公开（公告）日：2010-11-23
• [EN] BENZYLIC GLYCOSIDE DERIVATIVES AND METHODS OF USE<br/>[FR] DÉRIVÉS DE GLYCOSIDE BENZYLIQUE ET PROCÉDÉS D'UTILISATION
  申请人：THERACOS INC

  公开号：WO2008122014A1

  公开（公告）日：2008-10-09

  [EN] Provided are compounds having an inhibitory effect on sodium-dependent glucose cotransporter SGLT. The invention also provides pharmaceutical compositions, methods of preparing the compounds, synthetic intermediates, and methods of using the compounds, independently or in combination with other therapeutic agents, for treating diseases and conditions which are affected by SGLT inhibition.
  [FR] L'invention concerne des composés ayant un effet inhibiteur sur le cotransporteur de glucose dépendant du sodium SGLT. L'invention concerne également des compositions pharmaceutiques, des procédés de préparation des composés, des intermédiaires synthétiques et des procédés d'utilisation des composés, indépendamment ou en combinaison avec d'autres agents thérapeutiques, pour traiter des maladies ou affections qui sont affectées par l'inhibition du SGLT.