2-pentyl-5-phenyloxazole | 293306-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-pentyl-5-phenyloxazole
• 英文别名: 2-Pentyl-5-phenyl-1,3-oxazole；2-pentyl-5-phenyl-1,3-oxazole
• CAS: 293306-63-5
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: WQFPQTAUQNOYOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-pentyl-5-phenyloxazole 在 吡啶 、 盐酸 、 氯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-{4-[2-((R)-2-Hydroxy-2-pyridin-3-yl-ethylamino)-ethyl]-phenyl}-4-(2-pentyl-oxazol-5-yl)-benzenesulfonamide
  参考文献：
  名称：

  Substituted oxazole benzenesulfonamides as potent human β3 adrenergic receptor agonists

  摘要：

  As a part of our investigation into the development of orally bioavailable beta(3) adrenergic receptor agonists, we have identified a series of substituted oxazole derivatives that are potent beta(3) agonists with excellent selectivity against other beta receptors. Several of these compounds showed excellent oral bioavailability in dogs. One example, cyclopentylethyloxazole 5f is a potent beta(3) agonist (EC50 = 14 nM, 84% activation) with 340-fold and 160-fold selectivity over beta(1) and beta(2) receptors, respectively, and has 38% oral bioavailability in dogs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00277-8
• 作为产物：
  描述：

  在 亚磷酸三乙酯 作用下， 以 环己烷 为溶剂， 生成 2-pentyl-5-phenyloxazole
  参考文献：
  名称：

  Substituted oxazole benzenesulfonamides as potent human β3 adrenergic receptor agonists

  摘要：

  As a part of our investigation into the development of orally bioavailable beta(3) adrenergic receptor agonists, we have identified a series of substituted oxazole derivatives that are potent beta(3) agonists with excellent selectivity against other beta receptors. Several of these compounds showed excellent oral bioavailability in dogs. One example, cyclopentylethyloxazole 5f is a potent beta(3) agonist (EC50 = 14 nM, 84% activation) with 340-fold and 160-fold selectivity over beta(1) and beta(2) receptors, respectively, and has 38% oral bioavailability in dogs. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00277-8

文献信息

• Synthesis of Oxazoles through Copper-Mediated Aerobic Oxidative Dehydrogenative Annulation and Oxygenation of Aldehydes and Amines
  作者：Zejun Xu、Chun Zhang、Ning Jiao

  DOI：10.1002/anie.201206382

  日期：2012.11.5

  A fragment‐assembling strategy is used to form oxazoles from aryl acetaldehydes, amines, and molecular oxygen under mild conditions (see scheme). The transformation is highly efficient with the removal of six hydrogen atoms, including the cleavage of four C(sp3)H bonds.

  片段组装策略用于在温和条件下由芳基乙醛，胺和分子氧形成恶唑（请参阅方案）。通过去除六个氢原子，包括四个C（sp 3）H键的裂解，该转化过程非常高效。
• A facile synthesis of 2,5-disubstituted oxazoles via a copper-catalyzed cascade reaction of alkenes with azides
  作者：Jiu-ling Li、Ying-chun Wang、Wei-ze Li、Heng-shan Wang、Dong-liang Mo、Ying-ming Pan

  DOI：10.1039/c5cc06487b

  日期：——

  A novel and efficient approach to 2,5-disubstituted oxazoles is developed via a 1,3-dipolar cycloaddition/ring cleavage/1,2-H migration/denitrogenation/copper-catalyzed aerobic oxidative dehydrogenative cyclization cascade. The desired products can be obtained from readily available...

  通过1，3-偶极环加成/环裂解/ 1,2-H迁移/脱氮/铜催化的好氧氧化脱氢环化级联反应，开发了一种新颖，有效的2,5-二取代恶唑方法。所需的产品可以从容易获得的产品中获得。