dimethyl 2-((4-nitrophenyl)(1H-pyrrol-2-yl)methyl)malonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 2-((4-nitrophenyl)(1H-pyrrol-2-yl)methyl)malonate
• 英文别名: dimethyl 2-[(4-nitrophenyl)-(1H-pyrrol-2-yl)methyl]propanedioate
• 化学式: C₁₆H₁₆N₂O₆
• 分子量: 332.313
• InChiKey: YVQWPTLYBHXEJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  114
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl 2-((4-nitrophenyl)(1H-pyrrol-2-yl)methyl)malonate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以78%的产率得到methyl 1-(4-nitrophenyl)-3-oxo-2,3-dihydro-1H-pyrrolizine-2-carboxylate
  参考文献：
  名称：

  三氟乙酸tri催化吡咯的烷基化：3-氧代-2,3-二氢-1 H-吡咯嗪衍生物的有效合成

  摘要：

  在温和的反应条件下，通过Gd（OTf）3催化的吡咯与取代的2-苄叉基丙二酸二甲酯的加成反应，区域选择性地合成了新型的2-烷基化吡咯衍生物。2-烷基化吡咯衍生物用于构建3-氧代吡咯嗪骨架。烷基化吡咯衍生物的分子内环化提供了新的非对映选择性的3-氧代-2,3-二氢-1 H-吡咯嗪衍生物，具有良好或高产率。

  DOI：

  10.1016/j.tet.2007.04.018
• 作为产物：
  描述：

  吡咯 、 4-硝基苄烯丙二酸二甲酯 在 gadolinium(III) trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 以83%的产率得到dimethyl 2-((4-nitrophenyl)(1H-pyrrol-2-yl)methyl)malonate
  参考文献：
  名称：

  三氟乙酸tri催化吡咯的烷基化：3-氧代-2,3-二氢-1 H-吡咯嗪衍生物的有效合成

  摘要：

  在温和的反应条件下，通过Gd（OTf）3催化的吡咯与取代的2-苄叉基丙二酸二甲酯的加成反应，区域选择性地合成了新型的2-烷基化吡咯衍生物。2-烷基化吡咯衍生物用于构建3-氧代吡咯嗪骨架。烷基化吡咯衍生物的分子内环化提供了新的非对映选择性的3-氧代-2,3-二氢-1 H-吡咯嗪衍生物，具有良好或高产率。

  DOI：

  10.1016/j.tet.2007.04.018

文献信息

• Synthesis and highly potent anti-inflammatory activity of licofelone- and ketorolac-based 1-arylpyrrolizin-3-ones
  作者：Damian A. Madrigal、Carlos H. Escalante、Gabriel A. Gutiérrez-Rebolledo、José M. Cristobal-Luna、Omar Gómez-García、Roberto I. Hernández-Benitez、Ana L. Esquivel-Campos、Salud Pérez-Gutiérrez、Germán A. Chamorro-Cevallos、Francisco Delgado、Joaquín Tamariz

  DOI：10.1016/j.bmc.2019.115053

  日期：2019.10

  Since NSAIDs are commonly used anti-inflammatory agents that produce adverse effects, there have been ongoing efforts to develop more effective and less toxic compounds. Based on the structure of the anti-inflammatory pyrrolizines licofelone and ketorolac, a series of 1-arylpyrrolizin-3-ones was synthesized. Also prepared was a series of substituted pyrroles, mimicking similar known anti-inflammatory agents. The anti-inflammatory activity of the test compounds was determined with a phorbol ester (TPA)-induced murine ear edema protocol. For the most active derivatives, 19b-c/20b-c, the anti-inflammatory effect was the same as that of the reference compound (indomethacin) and was dose-dependent. These compounds have an aryl ring at the C-1 position and a methoxycarbonyl group at the C-2 position of the pyrrolizine framework, which represent plausible pharmacophore groups with anti-inflammatory activity. The anti-inflammatory activity of 1-substituted analogs containing a five-or six-membered heterocycles was lower but still good, while that of the pyrroles was only moderate. Although the docking studies suggests that the effect of analogs 19a-c/20a-c is associated with the inhibition of cyclooxygenase-2, experimental assays did not corroborate this idea. Indeed, a significant inhibition of NO was found experimentally as a plausible mechanism of action.
• Gadolinium triflate catalyzed alkylation of pyrroles: efficient synthesis of 3-oxo-2,3-dihydro-1H-pyrrolizine derivatives
  作者：Canan Unaleroglu、Arife Yazici

  DOI：10.1016/j.tet.2007.04.018

  日期：2007.6

  Novel 2-alkylated pyrrole derivatives were synthesized regioselectively by Gd(OTf)3 catalyzed addition reactions of pyrrole to substituted dimethyl 2-benzylidenemalonate derivatives under mild reaction conditions. 2-Alkylated pyrrole derivatives are used for the construction of the 3-oxo pyrrolizine skeleton. Intramolecular cyclization of alkylated pyrrole derivatives afforded new diastereoselective

  在温和的反应条件下，通过Gd（OTf）3催化的吡咯与取代的2-苄叉基丙二酸二甲酯的加成反应，区域选择性地合成了新型的2-烷基化吡咯衍生物。2-烷基化吡咯衍生物用于构建3-氧代吡咯嗪骨架。烷基化吡咯衍生物的分子内环化提供了新的非对映选择性的3-氧代-2,3-二氢-1 H-吡咯嗪衍生物，具有良好或高产率。