1,3-Dioxolane, 2-[[(3-methyl-3-oxetanyl)methoxy]methyl]-2-phenyl- | 497870-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-Dioxolane, 2-[[(3-methyl-3-oxetanyl)methoxy]methyl]-2-phenyl-
• 英文别名: 2-(3-methyloxetan-3-ylmethoxymethyl)-2-phenyl-1,3-dioxolane
• CAS: 497870-41-4
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: JSPMMUCKIOFCGD-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±37.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.94
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,3-Dioxolane, 2-[[(3-methyl-3-oxetanyl)methoxy]methyl]-2-phenyl- 在 硫酸 作用下， 反应 10.0h， 以63%的产率得到2-(3-methyloxetan-3-ylmethoxy)-1-phenylethanone
  参考文献：
  名称：

  Isomerization of cyclic ethers having a carbonyl functional group: new entries into different heterocyclic compounds

  摘要：

  Oxiranes (epoxides) and oxetanes having a carbonyl functional group are chemoselectively isomerized to different heterocyclic compounds via Lewis acid-promoted 1,6- and 1,7-intramolecular nucleophilic attacks of the carbonyl oxygen on the electron-deficient carbon neighboring the oxonium oxygen: for example, cyclic imides to bicyclic acetals, esters to bicyclic orthoesters, sec-amides to 4,5-dihydrooxazole or 5,6-dihydro-4H-1,3-oxazines, and tert-amides to bicyclic acetals or azetidines. The intramolecular attack of a 1,5-positioned carbonyl oxygen predominantly results in a propagating-end isomerization polymerization. On the other hand, cyclic ethers having a 1,8- or farther positioned carbonyl group undergo conventional ring-opening polymerization. A tetrahydrofuran (oxolane) ring does not open, even with a 1,6-positioned carbonyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00701-9
• 作为产物：
  描述：

  3 - 甲基-3-（对甲苯磺酰氧基甲基）环氧丙烷 在 sodium hydroxide 、 四丁基溴化铵 、 sodium iodide 作用下， 以 正己烷 、 丙酮 、 苯 为溶剂， 反应 15.0h， 生成 1,3-Dioxolane, 2-[[(3-methyl-3-oxetanyl)methoxy]methyl]-2-phenyl-
  参考文献：
  名称：

  Isomerization of cyclic ethers having a carbonyl functional group: new entries into different heterocyclic compounds

  摘要：

  Oxiranes (epoxides) and oxetanes having a carbonyl functional group are chemoselectively isomerized to different heterocyclic compounds via Lewis acid-promoted 1,6- and 1,7-intramolecular nucleophilic attacks of the carbonyl oxygen on the electron-deficient carbon neighboring the oxonium oxygen: for example, cyclic imides to bicyclic acetals, esters to bicyclic orthoesters, sec-amides to 4,5-dihydrooxazole or 5,6-dihydro-4H-1,3-oxazines, and tert-amides to bicyclic acetals or azetidines. The intramolecular attack of a 1,5-positioned carbonyl oxygen predominantly results in a propagating-end isomerization polymerization. On the other hand, cyclic ethers having a 1,8- or farther positioned carbonyl group undergo conventional ring-opening polymerization. A tetrahydrofuran (oxolane) ring does not open, even with a 1,6-positioned carbonyl group. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00701-9