[(2S,3S,6S)-3-chloro-2-prop-2-enoxy-3,6-dihydro-2H-pyran-6-yl]methanol | 1207071-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: [(2S,3S,6S)-3-chloro-2-prop-2-enoxy-3,6-dihydro-2H-pyran-6-yl]methanol
• CAS: 1207071-25-7
• 化学式: C₉H₁₃ClO₃
• 分子量: 204.653
• InChiKey: UPZSZTPGIMEILC-CIUDSAMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2S,3S,6S)-3-chloro-2-prop-2-enoxy-3,6-dihydro-2H-pyran-6-yl]methanol 、 2,6-二氯苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以51%的产率得到[(2S,3S,6S)-3-chloro-2-prop-2-enoxy-3,6-dihydro-2H-pyran-6-yl]methyl 2,6-dichlorobenzoate
  参考文献：
  名称：

  Synthesis and applications of a chiral-oxygenated 3-chloro-3,6-dihydro-2H-pyran obtained under Overman rearrangement conditions

  摘要：

  A chlorinated side product was formed under Overman rearrangement conditions from a trichloroacetimidate along with the expected allylic amide. The chlorinated product derived from a hex-2-enopyranoside was obtained in a totally stereoselective manner, and it can be a useful synthetic intermediate for chlorinated sugars. In order to improve the isolated yields of either the expected Overman rearrangement product or the chlorinated compound, we carried out a thorough study on the experimental conditions. The application of the latter for the synthesis of potential calpain inhibitors is also reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.136
• 作为产物：
  描述：

  C₂₅H₃₁ClO₃Si 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到[(2S,3S,6S)-3-chloro-2-prop-2-enoxy-3,6-dihydro-2H-pyran-6-yl]methanol
  参考文献：
  名称：

  Synthesis and applications of a chiral-oxygenated 3-chloro-3,6-dihydro-2H-pyran obtained under Overman rearrangement conditions

  摘要：

  A chlorinated side product was formed under Overman rearrangement conditions from a trichloroacetimidate along with the expected allylic amide. The chlorinated product derived from a hex-2-enopyranoside was obtained in a totally stereoselective manner, and it can be a useful synthetic intermediate for chlorinated sugars. In order to improve the isolated yields of either the expected Overman rearrangement product or the chlorinated compound, we carried out a thorough study on the experimental conditions. The application of the latter for the synthesis of potential calpain inhibitors is also reported. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.10.136

文献信息

• Synthesis and applications of a chiral-oxygenated 3-chloro-3,6-dihydro-2H-pyran obtained under Overman rearrangement conditions
  作者：Ana Montero、Esperanza Benito、Bernardo Herradón

  DOI：10.1016/j.tetlet.2009.10.136

  日期：2010.1

  A chlorinated side product was formed under Overman rearrangement conditions from a trichloroacetimidate along with the expected allylic amide. The chlorinated product derived from a hex-2-enopyranoside was obtained in a totally stereoselective manner, and it can be a useful synthetic intermediate for chlorinated sugars. In order to improve the isolated yields of either the expected Overman rearrangement product or the chlorinated compound, we carried out a thorough study on the experimental conditions. The application of the latter for the synthesis of potential calpain inhibitors is also reported. (C) 2009 Elsevier Ltd. All rights reserved.