diethyl 3,5-diphenyl-1H-pyrrole-2,4-dicarboxylate | 3651-14-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl 3,5-diphenyl-1H-pyrrole-2,4-dicarboxylate
• 英文别名: 2,4-Diethoxycarbonyl-3,5-diphenyl-pyrrol
• CAS: 3651-14-7
• 化学式: C₂₂H₂₁NO₄
• 分子量: 363.413
• InChiKey: OXVMXZKQWBYDHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 3,5-diphenyl-1H-pyrrole-2,4-dicarboxylate 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.67h， 生成 1-methyl-3,5-diphenyl-2,4-bis(hydroxymethyl)pyrrole
  参考文献：
  名称：

  Vinylogous carbinolamine tumor inhibitors. 20. Comparison of the chemical reactivities and antineoplastic activities of .alpha.,.beta.-, .alpha.,.beta.'-, .beta.,.beta.'- and .alpha.,.alpha.'-bis[[[(2-propylamino)carbonyl]oxy]methyl] substituted pyrroles

  摘要：

  The bis[N-(2-propyl)carbamate] derivatives of 2,3-bis(hydroxymethyl)-4,5-diphenyl-1-methylpyrrole (4a), 3,4-bis-(hydroxymethyl)-2,5-diphenyl-1-methylpyrrole (4b), 2,4-bis(hydroxymethyl)-3,5-diphenyl-1-methylpyrrole (4c), and 2,5-bis(hydroxymethyl)-3,4-diphenyl-1-methylpyrrole (4d) were synthesized and the reactivities of the four compounds were compared using the model nucleophile 4-(p-nitrobenzyl)pyridine (NBP). No significant correlation was seen between NBP reactivity and either toxicity or antineoplastic activity in this series. Three compounds 4a, 4b, and 4c gave significant reproducible activity against P388 lymphocytic leukemia; the alpha,alpha'-bis(carbamate) 4d was inactive. The alpha,beta- and alpha,beta'-bis(carbamates) 4a and 4c were evaluated against a panel of mouse tumor homografts and human tumor xenografts implanted under the kidney capsule of mice.

  DOI：

  10.1021/jm00161a042
• 作为产物：
  描述：

  ethyl 3-amino-3-phenylprop-2-enoate 在 氧气 、 copper diacetate 、 platinum(II) 2,4-pentanedionate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 6.5h， 生成 diethyl 3,5-diphenyl-1H-pyrrole-2,4-dicarboxylate
  参考文献：
  名称：

  由简单腈串联合成四取代 NH 吡咯

  摘要：

  提出了一种从容易获得的芳基腈合成四取代N H 吡咯的简便串联一锅法，涉及使用氧化剂对β-烯氨基酯的溴化锌配合物进行氧化二聚，无需任何额外试剂。

  DOI：

  10.1002/asia.202100860

文献信息

• Divergent Synthesis of Multisubstituted Unsymmetric Pyrroles and Pyrrolin-4-ones from Enamino Esters via Copper-Catalyzed Aerobic Dimerization
  作者：Zhi-Wei Chen、Lei Zheng、Jin Liu

  DOI：10.1002/ejoc.201900341

  日期：2019.5.26

  An efficient strategy for copper‐catalyzed synthesis of multisubstituted unsymmetric pyrroles and pyrrolin‐4‐ones, under oxygen atmosphere, from enamino esters through oxidative cyclization and 1,2‐aryl migration was developed. The additive plays a crucial role in this divergent transformation, and these transformations have different mechanisms (radical and non‐radical).

  在氧气氛下，从烯氨基酯经氧化环化和1,2-芳基迁移，开发了一种高效的铜催化合成多取代不对称吡咯和吡咯啉-4-酮的策略。添加剂在这种发散的转换中起着至关重要的作用，并且这些转换具有不同的机制（自由基和非自由基）。
• LAW, KAM, WAH;LAI, TING-FONG;SAMMES, M. P.;KATRITZKY, A. R.;MAK, T. C. W., J. CHEM. SOC. PERKIN TRANS., 1984, N 1, 111-118
  作者：LAW, KAM, WAH、LAI, TING-FONG、SAMMES, M. P.、KATRITZKY, A. R.、MAK, T. C. W.

  DOI：——

  日期：——
• ANDERSON W. K.; HEIDER A. R., J. MED. CHEM., 29,(1986) N 11, 2392-2395
  作者：ANDERSON W. K.、 HEIDER A. R.

  DOI：——

  日期：——
• Tandem Synthesis of Tetrasubstituted <i>N</i> H Pyrroles from Simple Nitriles
  作者：Hyeongsu Kim、Zi Xuan、Ju Hyun Kim

  DOI：10.1002/asia.202100860

  日期：2021.11.2

  A facile tandem one-pot method for the synthesis of tetrasubstituted NH pyrroles from readily available aryl nitriles is presented, involving oxidative dimerization of the zinc bromide complexes of β-enaminoesters using an oxidant without any extra reagents.

  提出了一种从容易获得的芳基腈合成四取代N H 吡咯的简便串联一锅法，涉及使用氧化剂对β-烯氨基酯的溴化锌配合物进行氧化二聚，无需任何额外试剂。
• Vinylogous carbinolamine tumor inhibitors. 20. Comparison of the chemical reactivities and antineoplastic activities of .alpha.,.beta.-, .alpha.,.beta.'-, .beta.,.beta.'- and .alpha.,.alpha.'-bis[[[(2-propylamino)carbonyl]oxy]methyl] substituted pyrroles
  作者：Wayne K. Anderson、Arvela R. Heider

  DOI：10.1021/jm00161a042

  日期：1986.11

  The bis[N-(2-propyl)carbamate] derivatives of 2,3-bis(hydroxymethyl)-4,5-diphenyl-1-methylpyrrole (4a), 3,4-bis-(hydroxymethyl)-2,5-diphenyl-1-methylpyrrole (4b), 2,4-bis(hydroxymethyl)-3,5-diphenyl-1-methylpyrrole (4c), and 2,5-bis(hydroxymethyl)-3,4-diphenyl-1-methylpyrrole (4d) were synthesized and the reactivities of the four compounds were compared using the model nucleophile 4-(p-nitrobenzyl)pyridine (NBP). No significant correlation was seen between NBP reactivity and either toxicity or antineoplastic activity in this series. Three compounds 4a, 4b, and 4c gave significant reproducible activity against P388 lymphocytic leukemia; the alpha,alpha'-bis(carbamate) 4d was inactive. The alpha,beta- and alpha,beta'-bis(carbamates) 4a and 4c were evaluated against a panel of mouse tumor homografts and human tumor xenografts implanted under the kidney capsule of mice.