3-[(5-Chloro-2-[(chloromethyl)oxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3 H)-one | 233676-45-4

• 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-[(5-Chloro-2-[(chloromethyl)oxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3 H)-one
• 英文别名: 3-[(5-Chloro-2-[(chloromethyl)oxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one；3-[2-(Chloromethoxy)-5-chlorobenzyl]-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1,3,4-oxadiazole-2-one；3-[[5-chloro-2-(chloromethoxy)phenyl]methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-one
• CAS: 233676-45-4
• 化学式: C₁₇H₁₁Cl₂F₃N₂O₃
• 分子量: 419.187
• InChiKey: QZHQLGGUHLOJFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  464.3±55.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-[(5-Chloro-2-[(chloromethyl)oxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3 H)-one 在 caesium carbonate 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 生成 [[[[4-Chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenoxy]methoxy]carbonyl]methyl]trimethylammonium methanesulfonate
  参考文献：
  名称：

  Synthesis of water-Soluble prodrugs of BMS-191011: A maxi-K channel opener targeted for post-stroke neuroprotection

  摘要：

  A variety of water-soluble prodrugs of BMS-191011 was synthesized and evaluated for solution state stability and rate of conversion to BMS-191011 in rat and human plasma. The deoxycarnitine ester prodrug (11c) was selected for clinical evaluation based on its superior chemical stability, crystallinity and cleavage to BMS-191011 in human plasma. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00296-8
• 作为产物：
  描述：

  3-(5-氯-2-羟基苄基)-5-(4-(三氟甲基)苯基)-1,3,4-噁二唑-2(3h)-酮 在 六甲基磷酰三胺 、 磺酰氯 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 生成 3-[(5-Chloro-2-[(chloromethyl)oxy]phenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3 H)-one
  参考文献：
  名称：

  Synthesis of water-Soluble prodrugs of BMS-191011: A maxi-K channel opener targeted for post-stroke neuroprotection

  摘要：

  A variety of water-soluble prodrugs of BMS-191011 was synthesized and evaluated for solution state stability and rate of conversion to BMS-191011 in rat and human plasma. The deoxycarnitine ester prodrug (11c) was selected for clinical evaluation based on its superior chemical stability, crystallinity and cleavage to BMS-191011 in human plasma. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00296-8

文献信息

• PHOSPHATE DERIVATIVES OF DIARYL 1,3,4-OXADIAZOLONE
  申请人：Bristol-Myers Squibb Company

  公开号：EP1056754B1

  公开（公告）日：2003-10-22
• US5939405A
  申请人：——

  公开号：US5939405A

  公开（公告）日：1999-08-17
• Synthesis of water-Soluble prodrugs of BMS-191011: A maxi-K channel opener targeted for post-stroke neuroprotection
  作者：Piyasena Hewawasam、Min Ding、Nathan Chen、Dalton King、Jay Knipe、Lorraine Pajor、Astrid Ortiz、Valentin K. Gribkoff、John Starrett

  DOI：10.1016/s0960-894x(03)00296-8

  日期：2003.5

  A variety of water-soluble prodrugs of BMS-191011 was synthesized and evaluated for solution state stability and rate of conversion to BMS-191011 in rat and human plasma. The deoxycarnitine ester prodrug (11c) was selected for clinical evaluation based on its superior chemical stability, crystallinity and cleavage to BMS-191011 in human plasma. (C) 2003 Elsevier Science Ltd. All rights reserved.