[7-[tert-butyl(diphenyl)silyl]oxy-3-[2-[2-(furan-2-yl)-1,3-dioxolan-2-yl]ethyl]-2-oxo-6,7-dihydro-5H-cyclopenta[b]pyran-4-yl] trifluoromethanesulfonate | 911856-56-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: [7-[tert-butyl(diphenyl)silyl]oxy-3-[2-[2-(furan-2-yl)-1,3-dioxolan-2-yl]ethyl]-2-oxo-6,7-dihydro-5H-cyclopenta[b]pyran-4-yl] trifluoromethanesulfonate
• CAS: 911856-56-9
• 化学式: C₃₄H₃₅F₃O₉SSi
• 分子量: 704.793
• InChiKey: UXSTZHXVZZCTNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [7-[tert-butyl(diphenyl)silyl]oxy-3-[2-[2-(furan-2-yl)-1,3-dioxolan-2-yl]ethyl]-2-oxo-6,7-dihydro-5H-cyclopenta[b]pyran-4-yl] trifluoromethanesulfonate 在 咪唑 、 三乙基硅烷 、 四(三苯基膦)钯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.33h， 生成 7-[tert-butyl(dimethyl)silyl]oxy-3-[2-[2-(furan-2-yl)-1,3-dioxolan-2-yl]ethyl]-6,7-dihydro-5H-cyclopenta[b]pyran-2-one
  参考文献：
  名称：

  Diastereoselective [4 + 4]-Photocycloaddition Reactions of Pyran-2-ones:  Rapid Access to Functionalized 5−8−5 Skeletons

  摘要：

  Fused bicyclic pyran-2-ones with pendant furan side chains and an oxygenated stereogenic center adjacent to the pyranone ring oxygen were prepared via FeCl3-catalyzed Michael addition. Irradiation furnished the corresponding lactone-bridged tricyclic [4+4]-cycloadducts with good facial selectivity. Surprisingly, the major isomer resulted from approach of the furan from the same face as the protected alcohol.

  DOI：

  10.1021/ol061576h
• 作为产物：
  描述：

  2-羟基环戊酮 在 吗啉 、 咪唑 、 三氯化铁 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 68.17h， 生成 [7-[tert-butyl(diphenyl)silyl]oxy-3-[2-[2-(furan-2-yl)-1,3-dioxolan-2-yl]ethyl]-2-oxo-6,7-dihydro-5H-cyclopenta[b]pyran-4-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Diastereoselective [4 + 4]-Photocycloaddition Reactions of Pyran-2-ones:  Rapid Access to Functionalized 5−8−5 Skeletons

  摘要：

  Fused bicyclic pyran-2-ones with pendant furan side chains and an oxygenated stereogenic center adjacent to the pyranone ring oxygen were prepared via FeCl3-catalyzed Michael addition. Irradiation furnished the corresponding lactone-bridged tricyclic [4+4]-cycloadducts with good facial selectivity. Surprisingly, the major isomer resulted from approach of the furan from the same face as the protected alcohol.

  DOI：

  10.1021/ol061576h

文献信息

• Diastereoselective [4 + 4]-Photocycloaddition Reactions of Pyran-2-ones:  Rapid Access to Functionalized 5−8−5 Skeletons
  作者：Dong Song、Robert McDonald、F. G. West

  DOI：10.1021/ol061576h

  日期：2006.8.1

  Fused bicyclic pyran-2-ones with pendant furan side chains and an oxygenated stereogenic center adjacent to the pyranone ring oxygen were prepared via FeCl3-catalyzed Michael addition. Irradiation furnished the corresponding lactone-bridged tricyclic [4+4]-cycloadducts with good facial selectivity. Surprisingly, the major isomer resulted from approach of the furan from the same face as the protected alcohol.