Tert-butyl 3-(2,2-dibromovinyl)azetidine-1-carboxylate | 1197419-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: Tert-butyl 3-(2,2-dibromovinyl)azetidine-1-carboxylate
• 英文别名: tert-butyl 3-(2,2-dibromoethenyl)azetidine-1-carboxylate
• CAS: 1197419-14-9
• 化学式: C₁₀H₁₅Br₂NO₂
• 分子量: 341.043
• InChiKey: HHYMZESVKOHDPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Tert-butyl 3-(2,2-dibromovinyl)azetidine-1-carboxylate 在 氯化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.33h， 以48%的产率得到tert-butyl 3-(2-bromovinyl)azetidine-1-carboxylate
  参考文献：
  名称：

  Structure based design of novel irreversible FAAH inhibitors

  摘要：

  Fatty acid amide hydrolase ( FAAH) has attracted significant attention due to its promise as an analgesic target. This has resulted in the discovery of numerous chemical classes as inhibitors of this potential therapeutic target. In this paper we disclose a new series of novel FAAH irreversible azetidine urea inhibitors. In general these compounds illustrate potent activity against the rat FAAH enzyme. Our SAR studies allowed us to optimize this series resulting in the identification of compounds 13 which were potent inhibitors of both human and rat enzyme. This series of compounds illustrated good hydrolase selectivity along with good PK properties. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.101
• 作为产物：
  描述：

  3-甲酰基氮杂环丁烷-1-羧酸叔丁酯 、 四溴化碳 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到Tert-butyl 3-(2,2-dibromovinyl)azetidine-1-carboxylate
  参考文献：
  名称：

  Structure based design of novel irreversible FAAH inhibitors

  摘要：

  Fatty acid amide hydrolase ( FAAH) has attracted significant attention due to its promise as an analgesic target. This has resulted in the discovery of numerous chemical classes as inhibitors of this potential therapeutic target. In this paper we disclose a new series of novel FAAH irreversible azetidine urea inhibitors. In general these compounds illustrate potent activity against the rat FAAH enzyme. Our SAR studies allowed us to optimize this series resulting in the identification of compounds 13 which were potent inhibitors of both human and rat enzyme. This series of compounds illustrated good hydrolase selectivity along with good PK properties. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.101

文献信息

• Structure based design of novel irreversible FAAH inhibitors
  作者：Jane L. Wang、Scott J. Bowen、Barbara A. Schweitzer、Heather M. Madsen、Joseph McDonald、Matthew J. Pelc、Ruth E. Tenbrink、David Beidler、Atli Thorarensen

  DOI：10.1016/j.bmcl.2009.07.101

  日期：2009.10

  Fatty acid amide hydrolase ( FAAH) has attracted significant attention due to its promise as an analgesic target. This has resulted in the discovery of numerous chemical classes as inhibitors of this potential therapeutic target. In this paper we disclose a new series of novel FAAH irreversible azetidine urea inhibitors. In general these compounds illustrate potent activity against the rat FAAH enzyme. Our SAR studies allowed us to optimize this series resulting in the identification of compounds 13 which were potent inhibitors of both human and rat enzyme. This series of compounds illustrated good hydrolase selectivity along with good PK properties. (C) 2009 Elsevier Ltd. All rights reserved.