Methyl 6-[2-(3-chloropropyl)-1,3-oxazol-5-yl]hex-2-ynoate | 146941-21-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: Methyl 6-[2-(3-chloropropyl)-1,3-oxazol-5-yl]hex-2-ynoate
• CAS: 146941-21-1
• 化学式: C₁₃H₁₆ClNO₃
• 分子量: 269.728
• InChiKey: STINGWGPWDOYFR-UHFFFAOYSA-N

物化性质

• 沸点：
  403.9±35.0 °C(Predicted)
• 密度：
  1.181±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 6-[2-(3-chloropropyl)-1,3-oxazol-5-yl]hex-2-ynoate 在 苯硅烷 、 cesium fluoride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 26.0h， 生成 Methyl 8-oxo-1,2,3,5,6,7-hexahydropyrrolo[1,2-a]indole-4-carboxylate
  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：

  己基-5-壬基氯 在 palladium dichloride 三氟化硼乙醚 、 sodium acetate 、 copper dichloride 作用下， 以 乙醚 为溶剂， 反应 17.5h， 生成 Methyl 6-[2-(3-chloropropyl)-1,3-oxazol-5-yl]hex-2-ynoate
  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