trans-3-azido-2-(phenylseleno)tetrahydropyran | 136061-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: trans-3-azido-2-(phenylseleno)tetrahydropyran
• 英文别名: (2R,3S)-3-azido-2-phenylselanyloxane
• CAS: 136061-75-1
• 化学式: C₁₁H₁₃N₃OSe
• 分子量: 282.204
• InChiKey: OZXNSQUUPNTWAL-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 trans-3-azido-2-(phenylseleno)tetrahydropyran 在 双氧水 作用下， 以74%的产率得到cis-3-azido-2-methoxytetrahydropyran
  参考文献：
  名称：

  Novel azido-phenylselenenylation of double bonds. Evidence for a free-radical process

  摘要：

  A simple and mild azido-phenylselenenylation of terminal alkenes, which proceeds with complete anti-Markovnikov regioselectivity, has been developed. This reaction occurs when the alkenes are treated with (diacetoxyiodo)benzene, sodium azide, and diphenyl diselenide in dichloromethane at room temperature. The observed regioselectivity can be explained by assuming that the addition process is initiated by azido radicals. This was further supported by the results obtained starting from 1,6-heptadiene and from beta-pinene. Under the same conditions, efficient azido-phenylselenenylation of symmetrical olefins, 3,4-dihydro-2H-pyran, methyl acrylate, and vinyl crotonate can also be effected.

  DOI：

  10.1021/jo00024a020
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 二苯基二硒醚 在 sodium azide 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以81%的产率得到trans-3-azido-2-(phenylseleno)tetrahydropyran
  参考文献：
  名称：

  Novel azido-phenylselenenylation of double bonds. Evidence for a free-radical process

  摘要：

  A simple and mild azido-phenylselenenylation of terminal alkenes, which proceeds with complete anti-Markovnikov regioselectivity, has been developed. This reaction occurs when the alkenes are treated with (diacetoxyiodo)benzene, sodium azide, and diphenyl diselenide in dichloromethane at room temperature. The observed regioselectivity can be explained by assuming that the addition process is initiated by azido radicals. This was further supported by the results obtained starting from 1,6-heptadiene and from beta-pinene. Under the same conditions, efficient azido-phenylselenenylation of symmetrical olefins, 3,4-dihydro-2H-pyran, methyl acrylate, and vinyl crotonate can also be effected.

  DOI：

  10.1021/jo00024a020

文献信息

• Novel azido-phenylselenenylation of double bonds. Evidence for a free-radical process
  作者：Marco Tingoli、Marcello Tiecco、Donatella Chianelli、Roberta Balducci、Andrea Temperini

  DOI：10.1021/jo00024a020

  日期：1991.11

  A simple and mild azido-phenylselenenylation of terminal alkenes, which proceeds with complete anti-Markovnikov regioselectivity, has been developed. This reaction occurs when the alkenes are treated with (diacetoxyiodo)benzene, sodium azide, and diphenyl diselenide in dichloromethane at room temperature. The observed regioselectivity can be explained by assuming that the addition process is initiated by azido radicals. This was further supported by the results obtained starting from 1,6-heptadiene and from beta-pinene. Under the same conditions, efficient azido-phenylselenenylation of symmetrical olefins, 3,4-dihydro-2H-pyran, methyl acrylate, and vinyl crotonate can also be effected.