cis-2,5-diethoxy-2',5'-dihydroxymethyl-1,4-dioxane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2,5-diethoxy-2',5'-dihydroxymethyl-1,4-dioxane
• 英文别名: [(2S,5S)-2,5-diethoxy-5-(hydroxymethyl)-1,4-dioxan-2-yl]methanol
• 化学式: C₁₀H₂₀O₆
• 分子量: 236.265
• InChiKey: NKGLBIUNLDMHDY-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 cis-2,5-diethoxy-2',5'-dihydroxymethyl-1,4-dioxane 在 吡啶 作用下， 以64%的产率得到cis-2,5-diethoxy-1,4-dioxane-2,5-dimethanol O-2¹,O-5¹-bis-p-toluenesulfonate
  参考文献：
  名称：

  Studies on the unusual stability of cis-2,5-diethoxy-2,5-bis(hydroxymethyl)-1,4-dioxane

  摘要：

  Almost equal amounts of the trans and cis isomers of 2,5-diethoxy-2,5-bis(hydroxymethyl)-1,4-dioxane (2trans and 2cis) are obtained by treating dihydroxyacetone with acidic ethanol. To explain the formation of an unusually large quantity of 2cis, conformation analyses and equilibration experiments were performed for the related compounds. The results indicate that the stability of 2cis derives not from the hydroxymethyl groups but from the unusually stable twist-boat conformation. The factors stabilizing the twist-boat conformation in 2cis were discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00003-4
• 作为产物：
  描述：

  1,3-dihydroxyacetone dimer 、 原甲酸三乙酯 在 硫酸 作用下， 反应 5.0h， 以35%的产率得到trans-2,5-diethoxy-2,5-bis(hydroxymethyl)-[1,4]-dioxane
  参考文献：
  名称：

  Studies on the unusual stability of cis-2,5-diethoxy-2,5-bis(hydroxymethyl)-1,4-dioxane

  摘要：

  Almost equal amounts of the trans and cis isomers of 2,5-diethoxy-2,5-bis(hydroxymethyl)-1,4-dioxane (2trans and 2cis) are obtained by treating dihydroxyacetone with acidic ethanol. To explain the formation of an unusually large quantity of 2cis, conformation analyses and equilibration experiments were performed for the related compounds. The results indicate that the stability of 2cis derives not from the hydroxymethyl groups but from the unusually stable twist-boat conformation. The factors stabilizing the twist-boat conformation in 2cis were discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00003-4

文献信息

• Dihydroxyacetone dimers; solution and crystal structure of stereoisomers of 2,5-diethoxy-1,4-dioxane-2,5-dimethanol
  作者：Viggo Waagen、Tilak K Barua、Henrik W Anthonsen、Lars K Hansen、Dag-J Fossli、Edward Hough、Thorleif Anthonsen

  DOI：10.1016/s0040-4020(01)89621-6

  日期：1994.1

  1,3-Dihydroxy-2-propanone (dihydroxyacetone) in aqueous solution is an equilibrium remeniscent of the one in ketoses. When reacted with triethyl orthoformate and ethanol two stable diethyl ethers were isolated and their structures have been shown to be the cis- and trans-isomers of 2,5-diethoxy-1,4-dioxane-2,5-dimethanol. NMR spectroscopy and X-ray crystallography revealed that the trans-isomer adapts

  水溶液中的1，3-二羟基-2-丙酮（二羟基丙酮）是酮糖中的一种平衡成分。当与原甲酸三乙酯和乙醇反应时，分离出两个稳定的二乙醚，其结构已显示为2,5-二乙氧基-1,4-二恶烷-2,5-二甲醇的顺式和反式异构体。NMR光谱和X射线晶体学显示，反式异构体适应椅子构象，而顺式异构体在溶液和结晶状态下都是扭曲舟。