methyl (1RS)-1-[(2-methyl-1,3-dioxo-1,2,3,4,5,6-hexahydrocyclopenta[c]pyrrol-5-yl)methyl]-2-oxocyclopent-3-ene carboxylate | 1415923-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (1RS)-1-[(2-methyl-1,3-dioxo-1,2,3,4,5,6-hexahydrocyclopenta[c]pyrrol-5-yl)methyl]-2-oxocyclopent-3-ene carboxylate
• 英文别名: methyl 1-[(2-methyl-1,3-dioxo-5,6-dihydro-4H-cyclopenta[c]pyrrol-5-yl)methyl]-2-oxocyclopent-3-ene-1-carboxylate
• CAS: 1415923-87-3
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: ZADNFAFEJKVIPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (1RS)-1-[(2-methyl-1,3-dioxo-1,2,3,4,5,6-hexahydrocyclopenta[c]pyrrol-5-yl)methyl]-2-oxocyclopent-3-ene carboxylate 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以86%的产率得到methyl 2-hydroxy-1-[(1-hydroxy-2-methyl-3-oxo-1,2,3,4,5,6-hexahydrocyclopenta[c]pyrrol-5-yl)methyl]cyclopent-3-enecarboxylate
  参考文献：
  名称：

  An Entry to Functionalized 2,8-Ethanonoradamantane Derivatives

  摘要：

  The synthesis of a functionalized derivative containing the 2,8-ethanonoradamantane carbocyclic skeleton, whose key-step consists of an intramolecular Diels-Alder reaction, is described. Chemoselective reduction of an intermediate enone required protection of the maleimide function through their Diets-Alder adducts with furan.

  DOI：

  10.1021/jo302398c
• 作为产物：
  描述：

  methyl (1RS)-1-[(2-methyl-1,3-dioxo-1,2,3,4,5,6-hexahydrocyclopenta[c]pyrrol-5-yl)methyl]-2-oxocyclopentanecarboxylate 在 palladium diacetate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 16.5h， 生成 methyl (1RS)-1-[(2-methyl-1,3-dioxo-1,2,3,4,5,6-hexahydrocyclopenta[c]pyrrol-5-yl)methyl]-2-oxocyclopent-3-ene carboxylate
  参考文献：
  名称：

  An Entry to Functionalized 2,8-Ethanonoradamantane Derivatives

  摘要：

  The synthesis of a functionalized derivative containing the 2,8-ethanonoradamantane carbocyclic skeleton, whose key-step consists of an intramolecular Diels-Alder reaction, is described. Chemoselective reduction of an intermediate enone required protection of the maleimide function through their Diets-Alder adducts with furan.

  DOI：

  10.1021/jo302398c