trans-2-methyl-4-hydroxymethyl-1,3-dioxolane | 3674-22-4

• 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: trans-2-methyl-4-hydroxymethyl-1,3-dioxolane
• 英文别名: trans-4-hydroxymethyl-2-methyl-1,3-dioxolane；DL-trans-4-Hydroxymethyl-2-methyl-1,3-dioxolan；[(2R,4R)-2-Methyl-1,3-dioxolan-4-yl]methanol
• CAS: 3674-22-4
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: ZCYJBTKNPHKPPN-RFZPGFLSSA-N

物化性质

• 沸点：
  187.0±0.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• 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：

  trans-2-methyl-4-hydroxymethyl-1,3-dioxolane 、 环氧乙烷 在 sodium 作用下， 生成 trans-2-methyl-4-<(2-hydroxyethoxy)methyl>-1,3-dioxolane
  参考文献：
  名称：

  Weclas, Ludmila; Sokolowski, Adam; Burczyk, Bogdan, Polish Journal of Chemistry, 1982, vol. 56, # 3, p. 485 - 490

  摘要：

  DOI：
• 作为产物：
  描述：

  甘油 、 三聚乙醛 在 硫酸 作用下， 反应 10.0h， 生成 trans-2-methyl-5-hydroxy-1,3-dioxane 、 trans-2-methyl-4-hydroxymethyl-1,3-dioxolane 、 2-methyl-1,3-dioxan-5-ol 、 cis-4-Hydroxymethyl-2-methyl-1,3-dioxolan
  参考文献：
  名称：

  NMR spectra, MO calculations of spin-spin coupling constants and conformational analysis of substituted 1,3-dioxolanes

  摘要：

  AbstractThe NMR spectra of a number of 2,4‐disubstituted 1,3‐dioxolanes have been recorded and the proton chemical shifts and coupling constants derived from complete spectral analysis. Vicinal coupling constants were found to be dependent on the substituent at C‐4 and this effect is more pronounced for J(trans) of the C‐4‐C‐5 fragment. These coupling constants also indicate a homogeneous behaviour within a series with either a cis or trans configuration, although the cis behaviour differs from that of trans isomers. This has been interpreted in terms of definite ring conformations in substituted derivatives, while the unsubstituted 1,3‐dioxolane undergoes free pesudorotation. Calculations of coupling constants were performed by semi‐empirical MO methods, both for unsubstituted 1,3‐dioxolane and for C‐4 substituted derivatives in a large number of conformations, in order to compare calculated and experimental values; the correct order of J(cis) and J(trans) for 1,3‐dioxolane is obtained only by employing energies from ab‐initio MO calculations averaged over the pseudorotation circuit. For the C‐4 substituted compounds calculated coupling constants were employed in a ‘trial and error’ process for the identification of the preferred conformations of these compounds; a set of two torsional angles for each compound was derived which allows a tentative description of the geometry of each molecule. A criticism of these geometries is given according to the evidence available on the structure of substituted 1,3‐dioxolanes.

  DOI：

  10.1002/mrc.1270130105

文献信息

• Heterocyclic Acetals from Glycerol and Acetaldehyde in Port Wines:  Evolution with Aging
  作者：Antonio Cesar da Silva Ferreira、Jean-Christophe Barbe、Alain Bertrand

  DOI：10.1021/jf011391j

  日期：2002.4.1

  In Port wine, isomers of glycerol and acetaldehyde acetals have been found at total contents ranging from 9.4 to 175.3 mg/L. During oxidative aging, the concentrations of the 5-hydroxy-2-methyl-1,3-dioxane and 4-hydroxymethyl-2-methyl-1,3-dioxolane isomers increased with time showing a linear correlation (r > 0.95). The flavor threshold for the mixture of the four isomers was evaluated in wine at 100

  在波特酒中，发现甘油和乙醛缩醛的异构体总含量为9.4至175.3 mg / L。在氧化老化过程中，5-羟基-2-甲基-1,3-二恶烷和4-羟基甲基-2-甲基-1,3-二恶戊烷的异构体的浓度随时间增加而呈线性关系（r> 0.95）。在葡萄酒中以100 mg / L评估四种异构体混合物的风味阈值。因此，预计它们会在30年以上的葡萄酒中产生“老波特酒”的香气。模型溶液和葡萄酒的实验清楚地表明，SO（2）与乙醛结合并阻止了乙缩醛化反应。
• WECLAS, L.;SOKOLOWSKI, A.;BURCZYK, B., POL. J. CHEM., 1982, 56, N 3, 485-490
  作者：WECLAS, L.、SOKOLOWSKI, A.、BURCZYK, B.

  DOI：——

  日期：——
• NMR spectra, MO calculations of spin-spin coupling constants and conformational analysis of substituted 1,3-dioxolanes
  作者：Rois Benassi、Luisa Schenetti、Ferdinando Taddei、Luigi Villa、Vincenzo Ferri

  DOI：10.1002/mrc.1270130105

  日期：1980.1

  AbstractThe NMR spectra of a number of 2,4‐disubstituted 1,3‐dioxolanes have been recorded and the proton chemical shifts and coupling constants derived from complete spectral analysis. Vicinal coupling constants were found to be dependent on the substituent at C‐4 and this effect is more pronounced for J(trans) of the C‐4‐C‐5 fragment. These coupling constants also indicate a homogeneous behaviour within a series with either a cis or trans configuration, although the cis behaviour differs from that of trans isomers. This has been interpreted in terms of definite ring conformations in substituted derivatives, while the unsubstituted 1,3‐dioxolane undergoes free pesudorotation. Calculations of coupling constants were performed by semi‐empirical MO methods, both for unsubstituted 1,3‐dioxolane and for C‐4 substituted derivatives in a large number of conformations, in order to compare calculated and experimental values; the correct order of J(cis) and J(trans) for 1,3‐dioxolane is obtained only by employing energies from ab‐initio MO calculations averaged over the pseudorotation circuit. For the C‐4 substituted compounds calculated coupling constants were employed in a ‘trial and error’ process for the identification of the preferred conformations of these compounds; a set of two torsional angles for each compound was derived which allows a tentative description of the geometry of each molecule. A criticism of these geometries is given according to the evidence available on the structure of substituted 1,3‐dioxolanes.
• Weclas, Ludmila; Sokolowski, Adam; Burczyk, Bogdan, Polish Journal of Chemistry, 1982, vol. 56, # 3, p. 485 - 490
  作者：Weclas, Ludmila、Sokolowski, Adam、Burczyk, Bogdan

  DOI：——

  日期：——