1-(3,4-dimethoxyphenyl)-1H-pyrrole | 43053-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(3,4-dimethoxyphenyl)-1H-pyrrole
• 英文别名: 1-(3,4-dimethoxy-phenyl)-pyrrole；1-(3,4-dimethoxyphenyl)pyrrole
• CAS: 43053-76-5
• 化学式: C₁₂H₁₃NO₂
• mdl: MFCD05256306
• 分子量: 203.241
• InChiKey: ASUZZDGBNHWAMT-UHFFFAOYSA-N

物化性质

• 沸点：
  312.0±32.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  23.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-1H-pyrrole 以 乙腈 为溶剂， 反应 0.25h， 生成 N-[2-(4-chlorophenyl)ethyl]-2-[1-(3,4-dimethoxyphenyl)pyrrol-2-yl]-2-oxoacetamide
  参考文献：
  名称：

  2-Oxo-2-(phen-2-ylpyrrol-2-yl)acetamides as potential anxiolytic agents: Synthesis and affinity at the central benzodiazepine receptor

  摘要：

  A series N-substituted 2-hydroxy and 2-oxo-2-(phen-1-ylpyrrol-2-yl)acetamides were synthesized and their affinity at the benzodiazepine receptor tested. Isosteric replacement of the indolyl ring in previously described derivatives by a phen-1-ylpyrrole led to the synthesis of seven compounds 8-9, 12-14, 23 and 26 with benzodiazepine affinity (K-1 less than or equal to 0.90 mu M). Among these, 26 exhibits an interesting anxiolytic activity and weak lateral effects. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80009-3
• 作为产物：
  描述：

  2,5-二甲氧基四氢呋喃 、 3,4-二甲氧基苯胺 在 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.67h， 生成 1-(3,4-dimethoxyphenyl)-1H-pyrrole
  参考文献：
  名称：

  Pd/Cu-catalyzed dual C–H bond carbonylation towards the synthesis of fluorazones

  摘要：

  Pd催化的氧化性双C-H键活化/羰基化仍然是一个巨大挑战，因为会生成副产物通过C-C键形成。在这里，我们开发了一种直接的Pd/Cu催化的氧化性双C-H键羰基化过程，从易得的N-芳基吡咯和CO利用O2作为末端氧化剂，制备生物学和药用重要的氟酮。

  DOI：

  10.1039/c7cc01707c

文献信息

• Synthesis of <i>N</i>-Substituted Pyrroles Under Catalyst- and Solvent-Free Conditions
  作者：Katla Ramesh、Sabbavarapu Narayana Murthy、Yadavalli Venkata Durga Nageswar

  DOI：10.1080/00397911.2011.560744

  日期：2012.8.15

  N-Substituted pyrroles were synthesized under neat conditions by the reaction of aromatic amines with 2, 5-dimethoxytetrahydrofuran in excellent yields.
• New Pyrrole Derivatives with Potent Tubulin Polymerization Inhibiting Activity As Anticancer Agents Including Hedgehog-Dependent Cancer
  作者：Giuseppe La Regina、Ruoli Bai、Antonio Coluccia、Valeria Famiglini、Sveva Pelliccia、Sara Passacantilli、Carmela Mazzoccoli、Vitalba Ruggieri、Lorenza Sisinni、Alessio Bolognesi、Whilelmina Maria Rensen、Andrea Miele、Marianna Nalli、Romina Alfonsi、Lucia Di Marcotullio、Alberto Gulino、Andrea Brancale、Ettore Novellino、Giulio Dondio、Stefania Vultaggio、Mario Varasi、Ciro Mercurio、Ernest Hamel、Patrizia Lavia、Romano Silvestri

  DOI：10.1021/jm500561a

  日期：2014.8.14

  We synthesized 3-aroyl-1-arylpyrrole (ARAP) derivatives as potential anticancer agents having different substituents at the pendant 1-phenyl ring. Both the 1-phenyl ring and 3-(3,4,5-trimethoxyphenyl)carbonyl moieties were mandatory to achieve potent inhibition of tubulin polymerization, binding of colchicine to tubulin, and cancer cell growth. ARAP 22 showed strong inhibition of the P-glycoprotein-overexpressing NCI-ADR-RES and Messa/Dx5MDR cell lines. Compounds 22 and 27 suppressed in vitro the Hedgehog signaling pathway, strongly reducing luciferase activity in SAG treated NIH3T3 Shh-Light II cells, and inhibited the growth of medulloblastoma D283 cells at nanomolar concentrations. ARAPs 22 and 27 represent a new potent class of tubulin polymerization and cancer cell growth inhibitors with the potential to inhibit the Hedgehog signaling pathway.
• Pd/Cu-catalyzed dual C–H bond carbonylation towards the synthesis of fluorazones
  作者：Fan Liao、Renyi Shi、Yuchen Sha、Jianhui Xia、Weilin Liao、Aiwen Lei

  DOI：10.1039/c7cc01707c

  日期：——

  Pd catalyzed oxidative dual C–H bond activation/carbonylation still remains a great challenge due to the generation of by-products via C–C bond formation. Herein, we developed a straightforward Pd/Cu-catalyzed oxidative dual C–H bond carbonylation process to access biologically and pharmaceutically important fluorazones from easily available N-aryl pyrroles and CO utilizing O₂ as the terminal oxidant.

  Pd催化的氧化性双C-H键活化/羰基化仍然是一个巨大挑战，因为会生成副产物通过C-C键形成。在这里，我们开发了一种直接的Pd/Cu催化的氧化性双C-H键羰基化过程，从易得的N-芳基吡咯和CO利用O2作为末端氧化剂，制备生物学和药用重要的氟酮。
• 2-Oxo-2-(phen-2-ylpyrrol-2-yl)acetamides as potential anxiolytic agents: Synthesis and affinity at the central benzodiazepine receptor
  作者：Hugues Dumoulin、Michel Boulouard、Martine Daoust、Sylvain Rault

  DOI：10.1016/s0223-5234(98)80009-3

  日期：1998.3

  A series N-substituted 2-hydroxy and 2-oxo-2-(phen-1-ylpyrrol-2-yl)acetamides were synthesized and their affinity at the benzodiazepine receptor tested. Isosteric replacement of the indolyl ring in previously described derivatives by a phen-1-ylpyrrole led to the synthesis of seven compounds 8-9, 12-14, 23 and 26 with benzodiazepine affinity (K-1 less than or equal to 0.90 mu M). Among these, 26 exhibits an interesting anxiolytic activity and weak lateral effects. (C) Elsevier, Paris.