4-[(2E)-4-bromobut-2-enyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one | 404859-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[(2E)-4-bromobut-2-enyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one
• 英文别名: 4-[(E)-4-bromobut-2-enyl]-3-methyl-1,2,4-oxadiazol-5-one
• CAS: 404859-43-4
• 化学式: C₇H₉BrN₂O₂
• 分子量: 233.065
• InChiKey: ZGOQLCOFCGAHMP-NSCUHMNNSA-N

物化性质

• 沸点：
  267.9±50.0 °C(Predicted)
• 密度：
  1.57±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[(2E)-4-bromobut-2-enyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one 在 四丁基溴化铵 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 2.5h， 生成 4-((E)-4-Amino-but-2-enyl)-3-methyl-4H-[1,2,4]oxadiazol-5-one
  参考文献：
  名称：

  3-Methyl-4H-[1,2,4]-oxadiazol-5-one: a versatile synthon for protecting monosubstituted acetamidines

  摘要：

  The utilization of 3-methyl-4H-[1,2,4]-oxadiazol-5-one as a versatile protected acetamidine is demonstrated through employment in a variety of synthetic sequences. The potassium salt (2a) or the neutral form (2b) is alternatively shown to be superior for various synthetic reactions (i.e., alkylation, Michael addition, Mitsunobu) to incorporate side chains for further synthesis. The 3-methyl-4H-[1,2,4]-oxadiazol-5-one moiety was found to be stable to acid or base under non-aqueous conditions. It was also found to be stable to many reagents commonly used for organic synthesis. Despite this stability, the free acetamidine may be released by mild reduction including Lindlar hydrogenation or dissolving metal reductions. Alternatively, the hydroxyl amidine may be formed via alkaline hydrolysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.030
• 作为产物：
  描述：

  1,4-二溴-2-丁烯 、 3-methyl-[1,2,4]oxadiazol-5-one potassium salt 在 四丁基溴化铵 作用下， 以 丙酮 为溶剂， 反应 18.0h， 以50%的产率得到4-[(2E)-4-bromobut-2-enyl]-3-methyl-1,2,4-oxadiazol-5(4H)-one
  参考文献：
  名称：

  3-Methyl-4H-[1,2,4]-oxadiazol-5-one: a versatile synthon for protecting monosubstituted acetamidines

  摘要：

  The utilization of 3-methyl-4H-[1,2,4]-oxadiazol-5-one as a versatile protected acetamidine is demonstrated through employment in a variety of synthetic sequences. The potassium salt (2a) or the neutral form (2b) is alternatively shown to be superior for various synthetic reactions (i.e., alkylation, Michael addition, Mitsunobu) to incorporate side chains for further synthesis. The 3-methyl-4H-[1,2,4]-oxadiazol-5-one moiety was found to be stable to acid or base under non-aqueous conditions. It was also found to be stable to many reagents commonly used for organic synthesis. Despite this stability, the free acetamidine may be released by mild reduction including Lindlar hydrogenation or dissolving metal reductions. Alternatively, the hydroxyl amidine may be formed via alkaline hydrolysis. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.09.030

文献信息

• 2-Amino-2-alkyl-4 hexenoic and hexynoic acid derivatives useful as nitric oxide synthase inhibitors
  申请人：——

  公开号：US20020128510A1

  公开（公告）日：2002-09-12

  The present invention relates to 2-amino-2-alkyl-4 hexenoic and hexynoic acid derivatives and their use in therapy, in particular their use as nitric oxide synthase inhibitors.

  本发明涉及2-氨基-2-烷基-4-己烯酸和己炔酸衍生物及其在治疗中的用途，特别是它们作为一氧化氮合酶抑制剂的用途。
• 2-amino-2-alkyl-4 hexenoic and hexynoic acid derivatives useful as nitric oxide synthase inhibitors
  申请人：——

  公开号：US20040192779A1

  公开（公告）日：2004-09-30

  The present invention relates to 2-amino-2-alkyl-4 hexenoic and hexynoic acid derivatives and their use in therapy, in particular their use as nitric oxide synthase inhibitors.

  本发明涉及 2-氨基-2-烷基-4-己烯酸和己炔酸衍生物及其在治疗中的用途，特别是用作一氧化氮合酶抑制剂。
• 2-AMINO-2-ALKYL-4 HEXENOIC AND HEXYNOIC ACID DERIVATIVES USEFUL AS NITRIC OXIDE SYNTHASE INHIBITORS
  申请人：Pharmacia Corporation

  公开号：EP1317416A2

  公开（公告）日：2003-06-11
• US6756406B2
  申请人：——

  公开号：US6756406B2

  公开（公告）日：2004-06-29
• US7005450B2
  申请人：——

  公开号：US7005450B2

  公开（公告）日：2006-02-28