2-(4'-chlorobutyl)-5-phenyloxazole | 146941-05-1

• 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-(4'-chlorobutyl)-5-phenyloxazole
• 英文别名: 2-(4-Chlorobutyl)-5-phenyl-1,3-oxazole
• CAS: 146941-05-1
• 化学式: C₁₃H₁₄ClNO
• 分子量: 235.713
• InChiKey: CUHIREFDANFHJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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-(4'-chlorobutyl)-5-phenyloxazole 在 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以90%的产率得到2-Phenyl-5,6,7,8-tetrahydro-[1,3]oxazolo[3,2-a]pyridin-4-ium;iodide
  参考文献：
  名称：

  Oxazole activation for azomethine ylide trapping: singly and doubly tethered substrates

  摘要：

  Bicyclic oxazolium salts 18, 24, 37, and 44 can be generated from tethered haloalkyloxazoles by internal alkylation. Reductive alkylation of the oxazolium salts using CsF/PhSiH3 converts the salts initially into the corresponding 4-oxazoline derivatives. Subsequent electrocyclic ring opening generates stabilized azomethine ylides that can be trapped by suitable dipolarophiles. Intermolecular dipole trapping followed by DDQ oxidation affords the ring-fused pyrroles 22 and 26. When tethered alkynoates are used for internal dipole trapping, the adducts 38 and 45 can be obtained by a similar reductive activation sequence, followed by DDQ workup. Effective procedures for the internal oxazole N-alkylation step are described using an acetonitrile-trifluoroethanol solvent system. Also, an improved method for the generation of the dichlorocerium derivative of ethyl propiolate and intermolecular trapping by an aldehyde is reported.

  DOI：

  10.1021/jo00058a010
• 作为产物：
  描述：

  2-甲基-5-苯基-噁唑 、 1-氯-3-碘丙烷 在 正丁基锂 作用下， 生成 2-(4'-chlorobutyl)-5-phenyloxazole
  参考文献：
  名称：

  Oxazole activation for azomethine ylide trapping: singly and doubly tethered substrates

  摘要：

  Bicyclic oxazolium salts 18, 24, 37, and 44 can be generated from tethered haloalkyloxazoles by internal alkylation. Reductive alkylation of the oxazolium salts using CsF/PhSiH3 converts the salts initially into the corresponding 4-oxazoline derivatives. Subsequent electrocyclic ring opening generates stabilized azomethine ylides that can be trapped by suitable dipolarophiles. Intermolecular dipole trapping followed by DDQ oxidation affords the ring-fused pyrroles 22 and 26. When tethered alkynoates are used for internal dipole trapping, the adducts 38 and 45 can be obtained by a similar reductive activation sequence, followed by DDQ workup. Effective procedures for the internal oxazole N-alkylation step are described using an acetonitrile-trifluoroethanol solvent system. Also, an improved method for the generation of the dichlorocerium derivative of ethyl propiolate and intermolecular trapping by an aldehyde is reported.

  DOI：

  10.1021/jo00058a010

文献信息

• Oxazole activation for azomethine ylide trapping: singly and doubly tethered substrates
  作者：Edwin Vedejs、David W. Piotrowski

  DOI：10.1021/jo00058a010

  日期：1993.3

  Bicyclic oxazolium salts 18, 24, 37, and 44 can be generated from tethered haloalkyloxazoles by internal alkylation. Reductive alkylation of the oxazolium salts using CsF/PhSiH3 converts the salts initially into the corresponding 4-oxazoline derivatives. Subsequent electrocyclic ring opening generates stabilized azomethine ylides that can be trapped by suitable dipolarophiles. Intermolecular dipole trapping followed by DDQ oxidation affords the ring-fused pyrroles 22 and 26. When tethered alkynoates are used for internal dipole trapping, the adducts 38 and 45 can be obtained by a similar reductive activation sequence, followed by DDQ workup. Effective procedures for the internal oxazole N-alkylation step are described using an acetonitrile-trifluoroethanol solvent system. Also, an improved method for the generation of the dichlorocerium derivative of ethyl propiolate and intermolecular trapping by an aldehyde is reported.