dimethyl 2-diethoxyphosphoryl-5-methylsulfanyl-3,4-dihydro-2H-pyrrole-3,4-dicarboxylate | 144878-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: dimethyl 2-diethoxyphosphoryl-5-methylsulfanyl-3,4-dihydro-2H-pyrrole-3,4-dicarboxylate
• CAS: 144878-74-0
• 化学式: C₁₃H₂₂NO₇PS
• 分子量: 367.36
• InChiKey: KEGLATZGUCXPTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  氯硫基甲烷 、 异腈甲基磷酸二乙酯 、 富马酸二甲酯 在 aluminum oxide 、 氢氧化钾 作用下， 生成 dimethyl 2-diethoxyphosphoryl-5-methylsulfanyl-3,4-dihydro-2H-pyrrole-3,4-dicarboxylate
  参考文献：
  名称：

  Base mediated reactions in solid-liquid media. A 1,3-dipolar cycloaddition route to pyrrolines and pyrroles from imino chlorosulfides.

  摘要：

  Nitrile ylides, generated in basic conditions (HCI abstraction) from N-[tosylmethyl] and N-[diethoxyphosphorylmethyl] imino chlorosuifides, undergo 1,3-dipolar cycloadditions with electron-deficient dipolarophiles to produce pyrroles and pyrrolines. Heterogeneous media are found to furnish the best conditions for these reactions. One pyrrole can also be prepared from methyl N-[ethoxycarbonylmethyl] chiorothioimidate and dimethyl acetylenedicarboxylate on alumina-potassium fluoride mixture as solid support, under microwave irradiation.

  DOI：

  10.1016/s0040-4039(00)60030-8

文献信息

• Base mediated reactions in solid-liquid media. A 1,3-dipolar cycloaddition route to pyrrolines and pyrroles from imino chlorosulfides.
  作者：Fabienne Berrée、Evelyne Marchand、Georges Morel

  DOI：10.1016/s0040-4039(00)60030-8

  日期：1992.10

  Nitrile ylides, generated in basic conditions (HCI abstraction) from N-[tosylmethyl] and N-[diethoxyphosphorylmethyl] imino chlorosuifides, undergo 1,3-dipolar cycloadditions with electron-deficient dipolarophiles to produce pyrroles and pyrrolines. Heterogeneous media are found to furnish the best conditions for these reactions. One pyrrole can also be prepared from methyl N-[ethoxycarbonylmethyl] chiorothioimidate and dimethyl acetylenedicarboxylate on alumina-potassium fluoride mixture as solid support, under microwave irradiation.