(1S,6R)-7-(hydroxymethyl)spiro[2,4-dioxabicyclo[4.2.0]oct-7-ene-3,1'-cyclohexane]-5-one | 140710-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,6R)-7-(hydroxymethyl)spiro[2,4-dioxabicyclo[4.2.0]oct-7-ene-3,1'-cyclohexane]-5-one
• CAS: 140710-25-4
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: LLFSFRNIBQDCAB-VHSXEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,5-二氧杂螺[5.5]十一碳-3-烯-2-酮 、 2-丙炔-1-醇 以 乙酸乙酯 为溶剂， 以19%的产率得到(1S,6R)-7-(hydroxymethyl)spiro[2,4-dioxabicyclo[4.2.0]oct-7-ene-3,1'-cyclohexane]-5-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

文献信息

• Regio-, stereo-, and enantioselective synthesis of cyclobutanols by means of the photoaddition of 1,3-dioxin-4-ones and lipase-catalyzed acetylation
  作者：Masayuki Sato、Hirohide Ohuchi、Yoshito Abe、Chikara Kaneko

  DOI：10.1016/s0957-4166(00)80211-6

  日期：1992.1

  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.