(1R,2R,3S)-2-(tert-butyldiphenylsiloxymethyl)-3-methylcyclobutanol | 140852-33-1

• 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: (1R,2R,3S)-2-(tert-butyldiphenylsiloxymethyl)-3-methylcyclobutanol
• CAS: 140852-33-1
• 化学式: C₂₂H₃₀O₂Si
• 分子量: 354.565
• InChiKey: ZGFOXKHZCCFAQK-DZFGPLHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 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,3S)-2-(tert-butyldiphenylsiloxymethyl)-3-methylcyclobutanol 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以83%的产率得到(2S,3R)-2-(tert-butyldiphenylsiloxymethyl)-3-methylcyclobutanone
  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：

  (1S^*,2S^*,3R^*)-2-(tert-butyldiphenylsiloxymethyl)-3-methylcyclobutanol 生成 (1R,2R,3S)-2-(tert-butyldiphenylsiloxymethyl)-3-methylcyclobutanol
  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