5-cyclohexyl-1,3-dioxolan-4-ol | 172288-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 5-cyclohexyl-1,3-dioxolan-4-ol
• CAS: 172288-97-0
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: RBWYOSLENLVLIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  5-cyclohexyl-1,3-dioxolan-4-ol 在 indium 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 36.0h， 生成 (4S,5R)-4-Allyl-5-cyclohexyl-2,2-dimethyl-[1,3]dioxolane
  参考文献：
  名称：

  Addition of Allylindium Reagents to Aldehydes Substituted at C_α or C_β with Heteroatomic Functional Groups. Analysis of the Modulation in Diastereoselectivity Attainable in Aqueous, Organic, and Mixed Solvent Systems

  摘要：

  The stereochemical course of indium-promoted allylations to alpha- and beta-oxy aldehydes has been investigated in solvents ranging from anhydrous THF to pure H2O. The free hydroxyl derivatives react with excellent diastereofacial control to give significantly heightened levels of syn-1,2-diols and anti-1,3-diols. Relative reactivities were determined in the alpha-series, and the hydroxy aldehyde proved to be the most reactive substrate. This reactivity ordering suggests that the selectivity stems from chelated intermediates. The rate acceleration observed in water can be heightened by initial acidification. Indeed, the indium-promoted allylation reaction mixtures become increasingly acidic on their own. Preliminary attention has been accorded to salt effects, and tetraethylammonium bromide was found to exhibit a positive synergistic effect on product distribution. Finally, mechanistic considerations are presented in order to allow for assessment of the status of these unprecedented developments at this stage of advancement of the field.

  DOI：

  10.1021/ja953682c
• 作为产物：
  描述：

  1-环己基-2-丙醇 在 二甲基硫 、 臭氧 作用下， 生成 5-cyclohexyl-1,3-dioxolan-4-ol
  参考文献：
  名称：

  Addition of Allylindium Reagents to Aldehydes Substituted at C_α or C_β with Heteroatomic Functional Groups. Analysis of the Modulation in Diastereoselectivity Attainable in Aqueous, Organic, and Mixed Solvent Systems

  摘要：

  The stereochemical course of indium-promoted allylations to alpha- and beta-oxy aldehydes has been investigated in solvents ranging from anhydrous THF to pure H2O. The free hydroxyl derivatives react with excellent diastereofacial control to give significantly heightened levels of syn-1,2-diols and anti-1,3-diols. Relative reactivities were determined in the alpha-series, and the hydroxy aldehyde proved to be the most reactive substrate. This reactivity ordering suggests that the selectivity stems from chelated intermediates. The rate acceleration observed in water can be heightened by initial acidification. Indeed, the indium-promoted allylation reaction mixtures become increasingly acidic on their own. Preliminary attention has been accorded to salt effects, and tetraethylammonium bromide was found to exhibit a positive synergistic effect on product distribution. Finally, mechanistic considerations are presented in order to allow for assessment of the status of these unprecedented developments at this stage of advancement of the field.

  DOI：

  10.1021/ja953682c

文献信息

• Chelation control associated with organometallic addition reactions in water. The high stereoselectivity offered by α- and β-hydroxyl substituents obviates the need for protecting groups
  作者：L Paquette

  DOI：10.1016/00404-0399(50)1439o-

  日期：1995.9.18

  High stereoselectivities have been observed for indium-promoted allylations of alpha- and beta-hydroxy aldehydes in aqueous media, with strong implication that chelate control can continue to operate in water.
• Addition of Allylindium Reagents to Aldehydes Substituted at C_α or C_β with Heteroatomic Functional Groups. Analysis of the Modulation in Diastereoselectivity Attainable in Aqueous, Organic, and Mixed Solvent Systems
  作者：Leo A. Paquette、Thomas M. Mitzel

  DOI：10.1021/ja953682c

  日期：1996.1.1

  The stereochemical course of indium-promoted allylations to alpha- and beta-oxy aldehydes has been investigated in solvents ranging from anhydrous THF to pure H2O. The free hydroxyl derivatives react with excellent diastereofacial control to give significantly heightened levels of syn-1,2-diols and anti-1,3-diols. Relative reactivities were determined in the alpha-series, and the hydroxy aldehyde proved to be the most reactive substrate. This reactivity ordering suggests that the selectivity stems from chelated intermediates. The rate acceleration observed in water can be heightened by initial acidification. Indeed, the indium-promoted allylation reaction mixtures become increasingly acidic on their own. Preliminary attention has been accorded to salt effects, and tetraethylammonium bromide was found to exhibit a positive synergistic effect on product distribution. Finally, mechanistic considerations are presented in order to allow for assessment of the status of these unprecedented developments at this stage of advancement of the field.