(1R,2R)-1-acetoxymethyl-2-(tert-butyldiphenylsiloxy)cyclobutane | 140710-29-8

• 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: (1R,2R)-1-acetoxymethyl-2-(tert-butyldiphenylsiloxy)cyclobutane
• 英文别名: [(1R,2R)-2-[tert-butyl(diphenyl)silyl]oxycyclobutyl]methyl acetate
• CAS: 140710-29-8
• 化学式: C₂₃H₃₀O₃Si
• 分子量: 382.575
• InChiKey: SOMHUEIGFNPPAI-DENIHFKCSA-N

物化性质

• 沸点：
  425.5±27.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,2R)-1-acetoxymethyl-2-(tert-butyldiphenylsiloxy)cyclobutane 在 咪唑 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 (1R,2R)-2-(tert-butyldiphenylsiloxymethyl)cyclobutan-1-ol
  参考文献：
  名称：

  Regio-, stereo-, and enantioselective synthesis of cyclobutanols by means of the photoaddition of 1,3-dioxin-4-ones and lipase-catalyzed acetylation

  摘要：

  Homochiral cis-2-hydroxymethylcyclobutanols, their all cis 3-methyl, and 4-hydroxymethyl derivatives were synthesized from 1,3-dioxin-4-ones via cyclobutane ring formation by [2+2]photocycloaddition, dioxanone ring cleavage, and reduction, followed by lipase-catalyzed kinetic resolution of the resulted cyclobutanols. The chiral cyclobutanols thus obtained have been converted to the corresponding gamma-lactones which are potential precursors for a series of biologically active compounds.

  DOI：

  10.1016/s0957-4166(00)80211-6
• 作为产物：
  描述：

  (1R,2R,3S)-1-acetoxymethyl-2-(tert-butyldiphenylsiloxy)-3-hydroxymethylcyclobutane 在 RhCl(PPh₃)3 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 7.0h， 生成 (1R,2R)-1-acetoxymethyl-2-(tert-butyldiphenylsiloxy)cyclobutane
  参考文献：
  名称：

  Regio-, stereo-, and enantioselective synthesis of cyclobutanols by means of the photoaddition of 1,3-dioxin-4-ones and lipase-catalyzed acetylation

  摘要：

  Homochiral cis-2-hydroxymethylcyclobutanols, their all cis 3-methyl, and 4-hydroxymethyl derivatives were synthesized from 1,3-dioxin-4-ones via cyclobutane ring formation by [2+2]photocycloaddition, dioxanone ring cleavage, and reduction, followed by lipase-catalyzed kinetic resolution of the resulted cyclobutanols. The chiral cyclobutanols thus obtained have been converted to the corresponding gamma-lactones which are potential precursors for a series of biologically active compounds.

  DOI：

  10.1016/s0957-4166(00)80211-6