1-oxaspiro[4.4]nonan-3-ol | 1331825-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: 1-oxaspiro[4.4]nonan-3-ol
• 英文别名: 1-Oxaspiro[4.4]nonan-3-ol
• CAS: 1331825-49-0
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: IJYLVXISVKDBSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxaspiro[4.4]nonan-3-ol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到1-oxaspiro[4.4]nonan-3-one
  参考文献：
  名称：

  General procedure for the synthesis of spirocyclic 3-hydroxy- and 3-oxotetrahydrofurans containing carboand heterocyclic fragments

  摘要：

  Reactions of cyclopentanone, cyclohexanone, N-substituted pyrrolidin-3-one and piperidin-4-one, and tetrahydropyran-4-one with allyl bromide in the presence of zinc and ammonium chloride gave the corresponding geminal hydroxy allyl derivatives. Treatment of the latter with sodium periodate in the presence of sodium metabisulfite resulted in their oxidative cyclization with formation of oxa spirocyclic alcohols containing carbo- and heterocyclic fragments. Swern oxidation of the spiro alcohols afforded the corresponding ketones which were characterized as 2,4-dinitrophenylhydrazones.

  DOI：

  10.1134/s1070428011070207
• 作为产物：
  描述：

  1-丙-2-烯基环戊烷-1-醇 在 sodium periodate 、 sodium disulfite 作用下， 以 水 、 叔丁醇 为溶剂， 以48%的产率得到1-oxaspiro[4.4]nonan-3-ol
  参考文献：
  名称：

  General procedure for the synthesis of spirocyclic 3-hydroxy- and 3-oxotetrahydrofurans containing carboand heterocyclic fragments

  摘要：

  Reactions of cyclopentanone, cyclohexanone, N-substituted pyrrolidin-3-one and piperidin-4-one, and tetrahydropyran-4-one with allyl bromide in the presence of zinc and ammonium chloride gave the corresponding geminal hydroxy allyl derivatives. Treatment of the latter with sodium periodate in the presence of sodium metabisulfite resulted in their oxidative cyclization with formation of oxa spirocyclic alcohols containing carbo- and heterocyclic fragments. Swern oxidation of the spiro alcohols afforded the corresponding ketones which were characterized as 2,4-dinitrophenylhydrazones.

  DOI：

  10.1134/s1070428011070207

文献信息

• Dibutyltin oxide mediated diastereoselective cyclodehydration/sulfonylation of 1,2,4-triols
  作者：Makhosazana P. Gamedze、Comfort M. Nkambule

  DOI：10.1016/j.tetlet.2015.02.083

  日期：2015.4

  Dibutyltin oxide (Bu2SnO) mediated cyclodehydration or sulfonylation of 1,2,4-triols is predictably diastereoselective depending on the steric bulk of the substituents at C4. A larger difference (Delta A-value >1 kcal/mol) leads to the syn-1,2,4-triols favouring cyclodehydration (78-85%) to form 3-hydroxytetrahydrofurans, with the anti-1,2,4-triols favouring monosulfonylation (66-87%). Triols from symmetrical ketones preferentially undergo cyclodehydration in high yield (>75%) due to a gem-disubstituent effect. Thus, the 1,2,4-triols derived from simple cyclic ketones also favour cyclodehydration to form spirocyclic 3-hydroxytetrahydrofurans in 72-79% yields. (C) 2015 Elsevier Ltd. All rights reserved.
• General procedure for the synthesis of spirocyclic 3-hydroxy- and 3-oxotetrahydrofurans containing carboand heterocyclic fragments
  作者：A. I. Moskalenko、S. L. Belopukhov、A. A. Ivlev、V. I. Boev

  DOI：10.1134/s1070428011070207

  日期：2011.7

  Reactions of cyclopentanone, cyclohexanone, N-substituted pyrrolidin-3-one and piperidin-4-one, and tetrahydropyran-4-one with allyl bromide in the presence of zinc and ammonium chloride gave the corresponding geminal hydroxy allyl derivatives. Treatment of the latter with sodium periodate in the presence of sodium metabisulfite resulted in their oxidative cyclization with formation of oxa spirocyclic alcohols containing carbo- and heterocyclic fragments. Swern oxidation of the spiro alcohols afforded the corresponding ketones which were characterized as 2,4-dinitrophenylhydrazones.