2-(methylthio)-4-carbomethoxypyrrole | 106762-08-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(methylthio)-4-carbomethoxypyrrole
• 英文别名: methyl 5-(methylsulfanyl)-1H-pyrrole-3-carboxylate；methyl 5-methylsulfanyl-1H-pyrrole-3-carboxylate
• CAS: 106762-08-7
• 化学式: C₇H₉NO₂S
• 分子量: 171.22
• InChiKey: PQCNXKOLIBAGMP-UHFFFAOYSA-N

物化性质

• 熔点：
  67-70 °C
• 沸点：
  359.7±27.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-Methylsulfanyl-2-(toluene-4-sulfonyl)-3,4-dihydro-2H-pyrrole-3-carboxylic acid methyl ester 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2-(methylthio)-4-carbomethoxypyrrole
  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

• Silyl-substituted thioimidates as nitrile ylide equivalents
  作者：Albert Padwa、John R. Gasdaska、Gunter Hoffmanns、Hector Rebello

  DOI：10.1021/jo00382a011

  日期：1987.3
• PADWA A.; GASDASKA J. R.; HAFFMANNS G.; REBELLO H., J. ORG. CHEM., 52,(1987) N 6, 1027-1035
  作者：PADWA A.、 GASDASKA J. R.、 HAFFMANNS G.、 REBELLO H.

  DOI：——

  日期：——
• 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.