2-(phenylseleno)bicyclo<2.2.1>heptane | 135394-88-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(phenylseleno)bicyclo<2.2.1>heptane
• CAS: 135394-88-6
• 化学式: C₁₃H₁₆Se
• 分子量: 251.23
• InChiKey: VXJDQRCTQQKVFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  苯基溴化硒 、 exo-2-bromonorbornane 在 magnesium 作用下， 生成 2-(phenylseleno)bicyclo<2.2.1>heptane
  参考文献：
  名称：

  Photochemistry of phenyl thioethers and phenyl selenoethers. Radical vs. ionic behavior

  摘要：

  In analogy with alkyl iodides and bromides, the phenyl thio- and selenoethers 2a,b, 13a, 21b,c and 35 displayed competing radical and ionic photobehavior on irradiation in solution, via a mechanism thought to involve initial homolytic cleavage of the alkyl C-S or C-Se bond followed by electron transfer within the resulting radical pair cage (Scheme I). These are the first examples of ionic photobehavior to be recognized for the C-SAr and C-SeAr chromophores. The electronegatively substituted pentafluorophenyl analogues 2c, 13b, and 21d displayed enhanced ionic photobehavior. By contrast, the 4-methoxyphenyl derivative 21a exhibited almost exclusively radical behavior. The sulfoxide (2R*,R*S)-21f displayed principally radical behavior, accompanied by epimerization at sulfur. The quantum yields for the disappearance of the 2-norbornyl ethers 21b and 21c were 0.53-0.64 in solution and rose to 0.89-0.95 in the presence of suspended fumed silica. Irradiation of the phenyl thioether 21b on silica gel resulted in nucleophilic trapping by surface silanol groups to afford covalently bound material (33), which afforded chloride 34 on treatment with SOCl2. Irradiation of phenyl thioethers 2a and 35, phenyl selenoether 2b, or C6H5SH in allyl alcohol solutionafforded acetal 11, apparently via isomerization of some of the solvent to propanal (44) followed by acetalization. Irradiation of alcoholic solutions of aldehydes containing C6H5SH is a useful means of generating acetals under neutral conditions.

  DOI：

  10.1021/ja00019a030