| 1314239-79-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 1314239-79-6
• 化学式: C₂₃H₂₇BrO₇
• 分子量: 495.367
• InChiKey: WULJRVHZZJWQIT-HZQGQDIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.88
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  108.61
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  在 三乙基硅烷 、 4-二甲氨基吡啶 、 三氟化硼乙醚 、 碘 、 三乙胺 、 锌 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-(allyloxy)benzyl)-4-(pent-4-en-1-yl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  Glucosides with cyclic diarylpolynoid as novel C-aryl glucoside SGLT2 inhibitors

  摘要：

  Novel C-aryl glucoside SGLT2 inhibitors containing cyclic diarylpolynoid motif were designed and synthesized for biological evaluation. Alkylzinc bromides have been efficiently prepared by the direct insertion of zinc metal into alkyl bromides. The organozinc reagents underwent smooth Pd-catalyzed cross-coupling reactions. Subsequent ring closing metathesis using 2nd generation Grubbs catalyst successfully generated novel class of ansa-compounds. These glucosides with cyclic diarylpolynoids demonstrated moderate in vitro inhibitory activity against SGLT2 in this series to date (IC50 = 59.5-103 nM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.063
• 作为产物：
  描述：

  2-溴-5-碘苯甲酸 在 三乙基硅烷 、 aluminum (III) chloride 、 lithium chloro-isopropyl-magnesium chloride 、 草酰氯 、 三氟化硼乙醚 、 三溴化硼 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 38.0h， 生成
  参考文献：
  名称：

  Glucosides with cyclic diarylpolynoid as novel C-aryl glucoside SGLT2 inhibitors

  摘要：

  Novel C-aryl glucoside SGLT2 inhibitors containing cyclic diarylpolynoid motif were designed and synthesized for biological evaluation. Alkylzinc bromides have been efficiently prepared by the direct insertion of zinc metal into alkyl bromides. The organozinc reagents underwent smooth Pd-catalyzed cross-coupling reactions. Subsequent ring closing metathesis using 2nd generation Grubbs catalyst successfully generated novel class of ansa-compounds. These glucosides with cyclic diarylpolynoids demonstrated moderate in vitro inhibitory activity against SGLT2 in this series to date (IC50 = 59.5-103 nM). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.063