3-[(Z)-3-(tert-Butyl-diphenyl-silanyl)-allyloxy]-2,2-difluoro-4,4-dimethyl-pentanoic acid ethyl ester | 145049-32-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-[(Z)-3-(tert-Butyl-diphenyl-silanyl)-allyloxy]-2,2-difluoro-4,4-dimethyl-pentanoic acid ethyl ester
• CAS: 145049-32-7
• 化学式: C₂₈H₃₈F₂O₃Si
• 分子量: 488.69
• InChiKey: XYPJSIYGOBCZOH-QNGOZBTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.77
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  3-[(Z)-3-(tert-Butyl-diphenyl-silanyl)-allyloxy]-2,2-difluoro-4,4-dimethyl-pentanoic acid ethyl ester 在 sodium tetrahydroborate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 Trifluoro-methanesulfonic acid 3-[(Z)-3-(tert-butyl-diphenyl-silanyl)-allyloxy]-2,2-difluoro-4,4-dimethyl-pentyl 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
• 作为产物：
  描述：

  特戊醛 在 sodium hydride 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-[(Z)-3-(tert-Butyl-diphenyl-silanyl)-allyloxy]-2,2-difluoro-4,4-dimethyl-pentanoic acid ethyl 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