(1R,2R)-2-(tert-butyldiphenylsiloxymethyl)cyclobutan-1-ol | 140852-31-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R)-2-(tert-butyldiphenylsiloxymethyl)cyclobutan-1-ol
• 英文别名: (1R,2R)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]cyclobutan-1-ol
• CAS: 140852-31-9
• 化学式: C₂₁H₂₈O₂Si
• 分子量: 340.538
• InChiKey: MLJYAMGTLRVBEO-YLJYHZDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.33
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-(tert-butyldiphenylsiloxymethyl)cyclobutan-1-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以92%的产率得到(R)-2-(tert-butyldiphenylsiloxymethyl)cyclobutan-1-one
  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：

  cis-2-(tert-butyldiphenylsiloxymethyl)cyclobutan-1-ol 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