(7R^*,7'R^*)-7-(1-hydroxypropyl)-1,4,8-trioxaspiro<4.5>decane | 140928-78-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7R^*,7'R^*)-7-(1-hydroxypropyl)-1,4,8-trioxaspiro<4.5>decane
• CAS: 140928-78-5
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: UZJYOAHRUNJATI-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (7R^*,7'R^*)-7-(1-hydroxypropyl)-1,4,8-trioxaspiro<4.5>decane 、 二苯二硫醚 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以60%的产率得到(2R^*,2'S^*)-7-<1-(phenylthio)propyl>-1,4,8-trioxaspiro<4.5>decane
  参考文献：
  名称：

  Diastereoselective cyclocondensation of electron-rich dienes with chiral thio-substituted aldehydes

  摘要：

  The Lewis acid-promoted cyclocondensation between two electron -rich dienes with a series of racemic alpha- and beta-thio-substituted aldehydes has been studied. Boron trifluoride etherate proved to be the catalyst of choice, affording satisfactory chemical yields and generally good diastereoselectivities. Other Lewis acidic catalysts gave lower yields and in some cases reversed the sense of the diastereoselection. A rationalization of the stereochemical results is presented.

  DOI：

  10.1021/jo00039a019
• 作为产物：
  描述：

  (S)-7-((S)-1-Benzyloxy-propyl)-1,4,8-trioxa-spiro[4.5]decane 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (7R^*,7'R^*)-7-(1-hydroxypropyl)-1,4,8-trioxaspiro<4.5>decane
  参考文献：
  名称：

  Diastereoselective cyclocondensation of electron-rich dienes with chiral thio-substituted aldehydes

  摘要：

  The Lewis acid-promoted cyclocondensation between two electron -rich dienes with a series of racemic alpha- and beta-thio-substituted aldehydes has been studied. Boron trifluoride etherate proved to be the catalyst of choice, affording satisfactory chemical yields and generally good diastereoselectivities. Other Lewis acidic catalysts gave lower yields and in some cases reversed the sense of the diastereoselection. A rationalization of the stereochemical results is presented.

  DOI：

  10.1021/jo00039a019