8-methylene-2-oxo-3,5-dioxabicyclo<4.2.0>octane-4-spirocyclohexane | 140710-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-methylene-2-oxo-3,5-dioxabicyclo<4.2.0>octane-4-spirocyclohexane
• 英文别名: 8-methylene-2-oxo-3,5-dioxabicyclo[4.2.0]octane-4-spirocyclohexane；7-methylidenespiro[2,4-dioxabicyclo[4.2.0]octane-3,1'-cyclohexane]-5-one
• CAS: 140710-13-0
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: JPURWPRJETWXQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-methylene-2-oxo-3,5-dioxabicyclo<4.2.0>octane-4-spirocyclohexane 在 palladium on activated charcoal 咪唑 、 硼烷四氢呋喃络合物 、 水 、 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 25.0~50.0 ℃ 、101.33 kPa 条件下， 反应 67.0h， 生成 (1S^*,2S^*,3R^*)-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
• 作为产物：
  描述：

  环己酮 以 乙酸乙酯 、 xylene 、 苯 为溶剂， 反应 0.5h， 生成 8-methylene-2-oxo-3,5-dioxabicyclo<4.2.0>octane-4-spirocyclohexane
  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.