diethyl 2-(3-methyloxetan-3-ylmethyl)malonate | 497870-36-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: diethyl 2-(3-methyloxetan-3-ylmethyl)malonate
• 英文别名: Diethyl 2-[(3-methyloxetan-3-yl)methyl]propanedioate
• CAS: 497870-36-7
• 化学式: C₁₂H₂₀O₅
• 分子量: 244.288
• InChiKey: UHQNQMBEOANWNH-UHFFFAOYSA-N

物化性质

• 沸点：
  291.4±10.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(3-methyloxetan-3-ylmethyl)malonate 在 水 、 甲铝双(2,6-二叔丁基-4-苯甲醚) 、 sodium chloride 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 101.0h， 生成 1-ethoxy-4-methyl-2,6-dioxabicyclo[2.2.2]octane
  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 ethanolate 、 sodium iodide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 4.5h， 生成 diethyl 2-(3-methyloxetan-3-ylmethyl)malonate
  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