methyl 5-phenyl-6-(phenylseleno)-4-oxa-2-hexenoate | 146896-32-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 5-phenyl-6-(phenylseleno)-4-oxa-2-hexenoate
• 英文别名: methyl 3-(1-phenyl-2-phenylselanylethoxy)prop-2-enoate
• CAS: 146896-32-4
• 化学式: C₁₈H₁₈O₃Se
• 分子量: 361.299
• InChiKey: IDRYEISXPGLKGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 5-phenyl-6-(phenylseleno)-4-oxa-2-hexenoate 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles

  摘要：

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.

  DOI：

  10.1021/jo00058a011
• 作为产物：
  描述：

  1-phenyl-2-(phenylselanyl)ethanol 、 丙炔酸甲酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以58%的产率得到methyl 5-phenyl-6-(phenylseleno)-4-oxa-2-hexenoate
  参考文献：
  名称：

  Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles

  摘要：

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.

  DOI：

  10.1021/jo00058a011

文献信息

• Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Francesca Marini

  DOI：10.1021/jo00058a011

  日期：1993.3

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.