2-n-hexyl-5-phenyloxazole | 293306-64-6

• 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-n-hexyl-5-phenyloxazole
• 英文别名: 2-hexyl-5-phenyloxazole；2-Hexyl-5-phenyl-1,3-oxazole；2-hexyl-5-phenyl-1,3-oxazole
• CAS: 293306-64-6
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: QECBSKWXUQAKBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-n-hexyl-5-phenyloxazole 在 吡啶 、 氯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2-{4-[4-(2-Hexyl-oxazol-5-yl)-benzenesulfonylamino]-phenyl}-ethyl)-((R)-2-hydroxy-2-pyridin-3-yl-ethyl)-carbamic acid tert-butyl ester
  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-n-hexyl-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

• Palladium‐ and Nickel‐Catalyzed Direct Alkylation of Azoles with Unactivated Alkyl Bromides and Chlorides
  作者：Tomoyuki Yao、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1002/chem.201001631

  日期：2010.11.2

  Long‐ing alkyl chain: The catalytic direct CH alkylation of azoles with unactivated alkyl bromides and chlorides is described. A palladium catalyst enables the alkylation of oxazoles, whereas a nickel one shows unique activity for thiazole. The catalyses allow a straightforward access to azole motifs bearing long, functional alkyl side chains.

  烷基长链：描述了未活化的烷基溴化物和氯化物对吡咯烷的催化直接CH烷基化反应。钯催化剂可以使恶唑烷基化，而镍催化剂对噻唑具有独特的活性。该催化剂允许直接获得带有长的功能性烷基侧链的唑基。
• Synthesis of 2,4- and 2,5-Disubstituted Oxazoles via Metal- Catalyzed Cross-Coupling Reactions
  作者：Carla M. Counceller、Chad C. Eichman、Nicolas Proust、James P. Stambuli

  DOI：10.1002/adsc.201000668

  日期：2011.1.10

  The rapid synthesis of 2,4‐ and 2,5‐disubstituted oxazoles via metal‐catalyzed cross‐coupling reactions is reported. The 4‐ or 5‐position of the corresponding 4‐ or 5‐halogenated 2‐butylthiooxazoles was successfully functionalized via Suzuki–Miyaura, Sonogashira and Stille cross‐coupling reactions. The 2‐position of the 2‐butylthiooxazoles obtained was further coupled to various organozinc reagents

  据报道，通过金属催化的交叉偶联反应可以快速合成2,4-二和2,5-二取代的恶唑。通过Suzuki-Miyaura，Sonogashira和Stille交叉偶联反应，成功地将相应的4或5卤代2丁基硫代恶唑的4或5位官能化。通过钯或镍介导的交叉偶联反应，将获得的2-丁基硫代恶唑的2-位进一步与各种有机锌试剂偶联。
• Substituted oxazole benzenesulfonamides as potent human β3 adrenergic receptor agonists
  作者：H.O. Ok、L.B. Reigle、M.R. Candelore、M.A. Cascieri、L.F. Colwell、L. Deng、W.P. Feeney、M.J. Forrest、G.J. Hom、D.E. MacIntyre、C.D. Strader、L. Tota、P. Wang、M.J. Wyvratt、M.H. Fisher、A.E. Weber

  DOI：10.1016/s0960-894x(00)00277-8

  日期：2000.7

  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.