methyl 2-(1-hydroxypropyl)-3-methylcycloprop-2-enecarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(1-hydroxypropyl)-3-methylcycloprop-2-enecarboxylate
• 英文别名: Methyl 2-(1-hydroxypropyl)-3-methylcycloprop-2-ene-1-carboxylate；methyl 2-(1-hydroxypropyl)-3-methylcycloprop-2-ene-1-carboxylate
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: NTDWXWZKEAMQEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(1-hydroxypropyl)-3-methylcycloprop-2-enecarboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 生成 2-methyl-3-propionyl-cycloprop-2-ene carboxylic acid methyl ester
  参考文献：
  名称：

  Chiral Cyclopropenyl Ketones: Reactive and Selective Diels–Alder Dienophiles

  摘要：

  The synthesis and Diels-Alder reactions of cyclopropenyl ketones are described. Cyclopropenyl ketones are highly reactive dienophiles that can engage a range of cyclic dienes and 2,3-dimethylbutadiene. The strategy of using cyclopropenyl ketones to facilitate Diels-Alder reactions is not limited to products that contain three-membered rings, as reductive opening by SmI2 can be used to produce a product that lacks a cyclopropane but retains a quaternary stereogenic center.

  DOI：

  10.1021/jo302683t
• 作为产物：
  描述：

  2-methylcycloprop-2-enecarboxylic acid 在 甲基锂 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.17h， 生成 methyl 2-(1-hydroxypropyl)-3-methylcycloprop-2-enecarboxylate
  参考文献：
  名称：

  Chiral Cyclopropenyl Ketones: Reactive and Selective Diels–Alder Dienophiles

  摘要：

  The synthesis and Diels-Alder reactions of cyclopropenyl ketones are described. Cyclopropenyl ketones are highly reactive dienophiles that can engage a range of cyclic dienes and 2,3-dimethylbutadiene. The strategy of using cyclopropenyl ketones to facilitate Diels-Alder reactions is not limited to products that contain three-membered rings, as reductive opening by SmI2 can be used to produce a product that lacks a cyclopropane but retains a quaternary stereogenic center.

  DOI：

  10.1021/jo302683t