2-furan-2-yl-4,4,6-trimethyl-[1,3]dioxane | 1204-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 2-furan-2-yl-4,4,6-trimethyl-[1,3]dioxane
• 英文别名: 2-(2-Furyl)-4,4,6-trimethyl-1,3-dioxane；2-(furan-2-yl)-4,4,6-trimethyl-1,3-dioxane
• CAS: 1204-54-2
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: SJVWZQYXFRLYQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-furan-2-yl-4,4,6-trimethyl-[1,3]dioxane 以26%的产率得到
  参考文献：
  名称：

  MASLINSKA-SOLICH J., J. CHEM. SOC. PERKIN TRANS. , 1975, PART 1, NO 6, 606-612

  摘要：

  DOI：
• 作为产物：
  描述：

  糠醛 、 2-甲基-2,4-戊二醇 在 硫酸 作用下， 以 水 为溶剂， 以72%的产率得到2-furan-2-yl-4,4,6-trimethyl-[1,3]dioxane
  参考文献：
  名称：

  Synthesis and structure analysis of cyclic furfural acetals

  摘要：

  Quantum chemical calculations and the PMR method are used to show that the preferable conformation of cyclic furfural acetals is a chair with an axial orientation of the furyl substituent. In 2-(furyl-2')-5-ethyl-5-oxymethyl-1,3-dioxane, the conformation equilibrium is shifted toward the trans-isomer with diaxial positions of the furyl and oxymethyl groups. The results of calculations suggest that the synthesis can lead to a cis-isomer with an axial orientation of the furyl and equatorial oxymethyl groups. It was shown experimentally that the synthesis leads to a mixture of trans- and cis-isomers. Mild conditions (room temperature, aqueous medium) lead to formation of the trans-isomer and small amounts of the cis-isomer (less than 2%). In rigid conditions (boiling in aromatic hydrocarbons), up to 20% of the cis-isomer is formed.

  DOI：

  10.1007/bf02763809

文献信息

• Synthesis and structure analysis of cyclic furfural acetals
  作者：G. A. Melnitskaya、A. Kh. Kuramshin、T. D. Khlebnikova、I. A. Melnitskii、E. A. Kantor

  DOI：10.1007/bf02763809

  日期：1997.11

  Quantum chemical calculations and the PMR method are used to show that the preferable conformation of cyclic furfural acetals is a chair with an axial orientation of the furyl substituent. In 2-(furyl-2')-5-ethyl-5-oxymethyl-1,3-dioxane, the conformation equilibrium is shifted toward the trans-isomer with diaxial positions of the furyl and oxymethyl groups. The results of calculations suggest that the synthesis can lead to a cis-isomer with an axial orientation of the furyl and equatorial oxymethyl groups. It was shown experimentally that the synthesis leads to a mixture of trans- and cis-isomers. Mild conditions (room temperature, aqueous medium) lead to formation of the trans-isomer and small amounts of the cis-isomer (less than 2%). In rigid conditions (boiling in aromatic hydrocarbons), up to 20% of the cis-isomer is formed.
• MASLINSKA-SOLICH J., J. CHEM. SOC. PERKIN TRANS. <JCPK-BH>, 1975, PART 1, NO 6, 606-612
  作者：MASLINSKA-SOLICH J.

  DOI：——

  日期：——