3,4-dihydro-6-[3'-hydroxy-1'-(para-toluenesulfonyl)-1'-butyl]-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-[3'-hydroxy-1'-(para-toluenesulfonyl)-1'-butyl]-2H-pyran
• 英文别名: 4-(3,4-dihydro-2H-pyran-6-yl)-4-(4-methylphenyl)sulfonylbutan-2-ol
• 化学式: C₁₆H₂₂O₄S
• 分子量: 310.414
• InChiKey: FNCDEEMVTONWFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-6-[3'-hydroxy-1'-(para-toluenesulfonyl)-1'-butyl]-2H-pyran 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 生成 (2RS,4SR,5RS)-2-methyl-4-(para-toluenesulfonyl)-1,6-dioxaspiro[4,5]decane 、 (2RS,4RS,5SR)-2-methyl-4-(para-toluenesulfonyl)-1,6-dioxaspiro[4,5]decane 、 (2RS,4RS,5RS)-2-methyl-4-(para-toluenesulfonyl)-1,6-dioxaspiro[4,5]decane 、 (2RS,4SR,5SR)-2-methyl-4-(para-toluenesulfonyl)-1,6-dioxaspiro[4,5]decane
  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：

  3,4-dihydro-6-[(p-toluenesulfonyl)methyl]-2H-pyran 、 methyloxirane 在 正丁基锂 、 六甲基磷酰三胺 、 三氟化硼乙醚 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以66%的产率得到3,4-dihydro-6-[3'-hydroxy-1'-(para-toluenesulfonyl)-1'-butyl]-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.