methyl 3-carbomethoxy-3-(α-pinyl)-3-hydroxy-2-oxopropanoate | 137946-20-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl 3-carbomethoxy-3-(α-pinyl)-3-hydroxy-2-oxopropanoate
• 英文别名: Dimethyl 2-[(6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl)methyl]-2-hydroxy-3-oxobutanedioate；dimethyl 2-[(6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl)methyl]-2-hydroxy-3-oxobutanedioate
• CAS: 137946-20-4；138125-64-1
• 化学式: C₁₆H₂₂O₆
• 分子量: 310.347
• InChiKey: MAEYEECGTSPVKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  dimethyl 2,3-dioxobutanedioate 、 (-)-β-蒎烯 以 甲苯 为溶剂， 反应 24.0h， 以58%的产率得到methyl 3-carbomethoxy-3-(α-pinyl)-3-hydroxy-2-oxopropanoate
  参考文献：
  名称：

  Ene reactions of dialkyl dioxosuccinate esters

  摘要：

  The ene reactions of dimethyl dioxosuccinate (1) and of diethyl dioxosuccinate (2) with olefins give the expected addition products. The reactions of 1 with vinyl ethers or an eneamine provide the cyclopentenones 15 and 16 in a sequence which is consistent with an ene reaction followed by a cyclization. The tin tetrachloride catalyzed conversion of 6 to 17 provides an example of a formal type II ene reaction to give a cyclopentyl ring. However, the stereochemistry of 17 suggests the reaction involves a stepwise ionic process.

  DOI：

  10.1021/jo00029a028

文献信息

• Ene reactions of dialkyl dioxosuccinate esters
  作者：Peter Beak、Zhiguo Song、James E. Resek

  DOI：10.1021/jo00029a028

  日期：1992.1

  The ene reactions of dimethyl dioxosuccinate (1) and of diethyl dioxosuccinate (2) with olefins give the expected addition products. The reactions of 1 with vinyl ethers or an eneamine provide the cyclopentenones 15 and 16 in a sequence which is consistent with an ene reaction followed by a cyclization. The tin tetrachloride catalyzed conversion of 6 to 17 provides an example of a formal type II ene reaction to give a cyclopentyl ring. However, the stereochemistry of 17 suggests the reaction involves a stepwise ionic process.