Imidazole-1-carbothioic acid O-{3-[(Z)-3-(tert-butyl-diphenyl-silanyl)-allyloxy]-2,2-difluoro-1-phenethyl-propyl} ester | 145049-60-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: Imidazole-1-carbothioic acid O-{3-[(Z)-3-(tert-butyl-diphenyl-silanyl)-allyloxy]-2,2-difluoro-1-phenethyl-propyl} ester
• 英文别名: O-[1-[(Z)-3-[tert-butyl(diphenyl)silyl]prop-2-enoxy]-2,2-difluoro-5-phenylpentan-3-yl] imidazole-1-carbothioate
• CAS: 145049-60-1
• 化学式: C₃₄H₃₈F₂N₂O₂SSi
• 分子量: 604.836
• InChiKey: XAMDIJLWIOVSSB-MXAYSNPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  68.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Imidazole-1-carbothioic acid O-{3-[(Z)-3-(tert-butyl-diphenyl-silanyl)-allyloxy]-2,2-difluoro-1-phenethyl-propyl} ester 在 偶氮二异丁腈 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 以2.5%的产率得到5-(tert-butyldiphenylsilyl)methyl-3,3-difluoro-4-(2-phenylethyl)tetrahydropyran
  参考文献：
  名称：

  Cyclization reactions of β,β-difluoroalkyl radicals (-CF2-C·) for synthesizing gem-difluorocyclic compounds

  摘要：

  Cyclization reactions of beta,beta-difluoroalkyl radicals were carried out. 5 or 6-Exo selective radical cyclizations gave gem-difluorocyclopentane or -cyclohexane derivatives in 53 - 96% yields. 2,5-Disubstituted-3,3-difluorotetrahydropyran derivatives were prepared in 36 - 82% yields with moderate trans-selectivity (2.0 : 1-3.1 : 1). 4,5-Disubstituted-3,3-difluorotetrahydopyran derivatives were obtained via radical deoxygenation in 60 - 74% yields. High stereo-selectivity of radical cyclization for the formation of gem-fluorotetrahydropyran rings was achieved by introducing the bulky TBDPS group onto the acceptor double bond.

  DOI：

  10.1016/s0040-4020(01)81990-6
• 作为产物：
  描述：

  tert-Butyl-{(Z)-3-[2,2-difluoro-5-phenyl-3-(tetrahydro-pyran-2-yloxy)-pentyloxy]-propenyl}-diphenyl-silane 在 对甲苯磺酸 乙醇 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 Imidazole-1-carbothioic acid O-{3-[(Z)-3-(tert-butyl-diphenyl-silanyl)-allyloxy]-2,2-difluoro-1-phenethyl-propyl} ester
  参考文献：
  名称：

  Cyclization reactions of β,β-difluoroalkyl radicals (-CF2-C·) for synthesizing gem-difluorocyclic compounds

  摘要：

  Cyclization reactions of beta,beta-difluoroalkyl radicals were carried out. 5 or 6-Exo selective radical cyclizations gave gem-difluorocyclopentane or -cyclohexane derivatives in 53 - 96% yields. 2,5-Disubstituted-3,3-difluorotetrahydropyran derivatives were prepared in 36 - 82% yields with moderate trans-selectivity (2.0 : 1-3.1 : 1). 4,5-Disubstituted-3,3-difluorotetrahydopyran derivatives were obtained via radical deoxygenation in 60 - 74% yields. High stereo-selectivity of radical cyclization for the formation of gem-fluorotetrahydropyran rings was achieved by introducing the bulky TBDPS group onto the acceptor double bond.

  DOI：

  10.1016/s0040-4020(01)81990-6