Dimethyl N-methyl-2-phenylpyrrole-3,4-dicarboxylate | 19611-52-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Dimethyl N-methyl-2-phenylpyrrole-3,4-dicarboxylate
• 英文别名: dimethyl 1-methyl-2-phenylpyrrole-3,4-dicarboxylate；1-methyl-2-phenyl-pyrrole-3,4-dicarboxylic acid dimethyl ester；1-Methyl-2-phenyl-3,4-pyrrolidindicarbonsaeuredimethylester；1-Methyl-2-phenylpyrrol-3,4-dicarbonsaeure-dimethylester；Dimethyl-1-methyl-2-phenylpyrrol-3,4-dicarboxylat；Dimethyl 1-methyl-2-phenyl-1H-pyrrole-3,4-dicarboxylate
• CAS: 19611-52-0
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: STWTYTHCPXHOAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  399.6±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Dimethyl N-methyl-2-phenylpyrrole-3,4-dicarboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以92%的产率得到[4-(hydroxymethyl)-1-methyl-5-phenylpyrrol-3-yl]methanol
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 19. Synthesis and antineoplastic activity of bis[[[(alkylamino)carbonyl]oxy]methyl]-substituted 3-pyrrolines as prodrugs of tumor inhibitory pyrrolebis(carbamates)

  摘要：

  A series of bis[(carbamoyloxy)methyl]pyrrolines 2-4 were synthesized from either the appropriate alpha-silylated iminium salt, or an aziridine, or a 2H-azirine in a sequence involving 1,3-dipolar cycloaddition reactions. The antineoplastic activities of the pyrrolines were compared to the corresponding pyrroles. The C-2 gem-dimethyl-substituted pyrroline, 4, which cannot be converted to the pyrrole in vivo, was inactive. The activity of the 2-phenyl-substituted pyrrolines 3 was markedly dependent on the nature of the phenyl substituent, although the corresponding phenylpyrroles all showed comparable activity. The differences in the activities of the pyrrolines 3 may be due to the rate of metabolic conversion of the pyrroline to the pyrrole. Electron-withdrawing substituents on the phenyl ring appear to retard this process.

  DOI：

  10.1021/jm00161a019
• 作为产物：
  描述：

  N-甲基苯甲酰胺 在 sodium hydroxide 、 cesium fluoride 作用下， 反应 28.0h， 生成 Dimethyl N-methyl-2-phenylpyrrole-3,4-dicarboxylate
  参考文献：
  名称：

  Generation of azomethine ylides via the desilylation reaction of immonium salts

  摘要：

  DOI：

  10.1021/jo00192a013

文献信息

• Unprecedented 1,4-stannatropy: effective generation of azomethine ylides as nitrile ylide equivalents from N-(stannylmethyl)thioamides
  作者：Mitsuo Komatsu、Yukihiro Kasano、Jin-ichi Yonemori、Yoji Oderaotoshi、Satoshi Minakata

  DOI：10.1039/b513413g

  日期：——

  Generation and cycloaddition of less- or non-stabilized azomethine ylides, or nitrile ylide equivalents, via unprecedented 1,4-stannatropy of N-(tributylstannylmethyl)thioamides were achieved. The reactions with dipolarophiles, such as electron-deficient alkenes and alkynes, afforded corresponding pyrrolidine and pyrrole derivatives effectively.

  通过空前的N-（三丁基锡烷基甲基）硫代酰胺的1,4-苯乙烯基转移反应，实现了稳定性更差或不稳定的甲亚胺基亚胺或腈基当量的生成和环加成。与偶极亲电子的反应，例如缺电子的烯烃和炔烃，有效地提供了相应的吡咯烷和吡咯衍生物。
• Cesium fluoride induced desilylation reaction of immonium salts derived from vinylogous amides
  作者：Albert Padwa、Gunter Haffmanns、Miguel Tomas

  DOI：10.1016/s0040-4039(00)88326-4

  日期：1983.1

  The cesium fluoride induced desilylation reaction of immonium salts derived from amides, thioamides and vinylogous amides provides access to reactive azomethine ylides in synthetically useful yields.

  氟化铯诱导的衍生自酰胺，硫代酰胺和乙烯基酰胺的铵盐的脱甲硅烷基化反应提供了以合成有用的产率获得反应性偶氮甲亚胺的途径。
• PADWA, A.;HAFFMANNS, G.;TOMAS, M., TETRAHEDRON LETT., 1983, 24, N 40, 4303-4306
  作者：PADWA, A.、HAFFMANNS, G.、TOMAS, M.

  DOI：——

  日期：——
• PADWA, A.;HAFFMANNS, G.;TOMAS, M., J. ORG. CHEM., 1984, 49, N 8, 3314-3322
  作者：PADWA, A.、HAFFMANNS, G.、TOMAS, M.

  DOI：——

  日期：——
• ANDERSON W. K.; MILOWSKY A. S., J. MED. CHEM., 29,(1986) N 11, 2241-2249
  作者：ANDERSON W. K.、 MILOWSKY A. S.

  DOI：——

  日期：——