3,4-dihydro-6-[5'-(t-butyldimethylsilyloxy)-1'-(para-toluenesulfonyl)-1'-pentyl]-2H-pyran

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,4-dihydro-6-[5'-(t-butyldimethylsilyloxy)-1'-(para-toluenesulfonyl)-1'-pentyl]-2H-pyran
• 英文别名: tert-butyl-[5-(3,4-dihydro-2H-pyran-6-yl)-5-(4-methylphenyl)sulfonylpentoxy]-dimethylsilane
• 化学式: C₂₃H₃₈O₄SSi
• 分子量: 438.704
• InChiKey: YJVHWXDEBJWDOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.02
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-6-[5'-(t-butyldimethylsilyloxy)-1'-(para-toluenesulfonyl)-1'-pentyl]-2H-pyran 在 盐酸 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 27.0h， 以95%的产率得到1,10-dihydroxy-6-(para-toluenesulfonyl)-5-decanone
  参考文献：
  名称：

  A new synthesis of spiroketals via sulfonyl-substituted dihydropyrans

  摘要：

  6,6- and 6,5-Spiroketals were prepared in good overall yields by alkylation and epoxide-opening reactions of 3,4-dihydro-6[(para-toluenesulfonyl)methyl]-2H-pyran (1) and subsequent acid catalysed cyclisation. The diastereoselectivity of the cyclisations was determined by a combination of 2D-NMR spectroscopy and X-ray crystallography. Attempted preparation of a 7,6-spiroketal using the same methodology was unsuccessful. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01026-7
• 作为产物：
  描述：

  叔丁基(4-碘丁氧基)二甲基硅烷 、 3,4-dihydro-6-[(p-toluenesulfonyl)methyl]-2H-pyran 在 正丁基锂 、 六甲基磷酰三胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以82%的产率得到3,4-dihydro-6-[5'-(t-butyldimethylsilyloxy)-1'-(para-toluenesulfonyl)-1'-pentyl]-2H-pyran
  参考文献：
  名称：

  A new synthesis of spiroketals via sulfonyl-substituted dihydropyrans

  摘要：

  6,6- and 6,5-Spiroketals were prepared in good overall yields by alkylation and epoxide-opening reactions of 3,4-dihydro-6[(para-toluenesulfonyl)methyl]-2H-pyran (1) and subsequent acid catalysed cyclisation. The diastereoselectivity of the cyclisations was determined by a combination of 2D-NMR spectroscopy and X-ray crystallography. Attempted preparation of a 7,6-spiroketal using the same methodology was unsuccessful. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01026-7

文献信息

• A new synthesis of spiroketals via sulfonyl-substituted dihydropyrans
  作者：Donald C Craig、Gavin L Edwards、David J Sinclair

  DOI：10.1016/s0040-4020(00)01026-7

  日期：2001.1

  6,6- and 6,5-Spiroketals were prepared in good overall yields by alkylation and epoxide-opening reactions of 3,4-dihydro-6[(para-toluenesulfonyl)methyl]-2H-pyran (1) and subsequent acid catalysed cyclisation. The diastereoselectivity of the cyclisations was determined by a combination of 2D-NMR spectroscopy and X-ray crystallography. Attempted preparation of a 7,6-spiroketal using the same methodology was unsuccessful. (C) 2001 Elsevier Science Ltd. All rights reserved.