(1R,2R)-2-hydroxymethylcyclobutan-1-ol | 140852-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R)-2-hydroxymethylcyclobutan-1-ol
• 英文别名: cis-2-(Hydroxymethyl)cyclobutan-1-ol；(1R,2R)-2-(hydroxymethyl)cyclobutan-1-ol
• CAS: 140852-37-5
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: VSYWGNKHUGJYOX-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-hydroxymethylcyclobutan-1-ol 在 咪唑 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (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：

  [(1R,2R)-2-hydroxycyclobutyl]methyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (1R,2R)-2-hydroxymethylcyclobutan-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