methyl 2-methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate | 1351758-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: methyl 2-methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
• 英文别名: methyl 5-methyl-3-oxo-1,2-dihydropyrrole-4-carboxylate
• CAS: 1351758-44-5
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: VSJDKHRQJZMXNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  267.1±40.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.39
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate 在 三乙烯二胺 、 potassium hydrogensulfate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.17h， 生成
  参考文献：
  名称：

  Mechanistic Insights into Annulation of Arylidene‐Δ ² ‐Pyrrolin‐4‐Ones by Cinchona Squaramide‐Based Organocatalysts

  摘要：

  AbstractArylidene‐Δ2‐pyrrolin‐4‐ones undergo organocatalyzed annulation with malononitrile, furnishing dihydropyrano[3,2‐b]pyrroles (18 examples, 0–77% ee in dichloromethane, 11–44% ee in methanol). The products could be enantiomerically enriched by trituration (11 examples, 95–99% ee). Enantioselectivity was dependent on the nature of the substrate and the conformation of the catalyst, which in turn was solvent‐controlled. The reaction mechanism, which included two pseudo‐enantiomeric organocatalyst conformations, was investigated by experimental and quantum chemical methods. The reaction mechanism consists of Michael addition reaction step followed by 6‐exo‐dig annulation, which was found to be the rate determining step. Additionally, it was identified that the preferred reaction pathway follows the model originally proposed by Pápai et al.magnified image

  DOI：

  10.1002/adsc.202101369
• 作为产物：
  描述：

  3-氨基巴豆酸甲酯 在 吡啶 、 potassium hydroxide 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 7.75h， 生成 methyl 2-methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  通过有机催化的Sulfa-Michael / Aldol Domino序列合成Spiro-Δ 2 -吡咯啉-4-酮假对映体

  摘要：

  Δ 2 -吡咯啉-4-酮与巯基乙醛二聚体进行有机催化的磺胺-迈克尔/奥尔多多米诺螺环化反应。该产品包含3个连续的立体中心（ ee 高达99％， dr 高达95：5，有25个示例），并且可以转化为天然产物的类似物。在使用单一催化剂的情况下，产物的绝对构型由起始材料的环外双键的构型决定。这些结果表明，不饱和Δ 2 -吡咯啉-4-酮可广泛用于各种（有机）催化（级联）转化中，以访问基于3D的吡咯烷酮（螺环）的库。杂环。

  DOI：

  10.1002/adsc.201900747

文献信息

• Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials
  作者：Dinakaran Murugesan、Alka Mital、Marcel Kaiser、David M. Shackleford、Julia Morizzi、Kasiram Katneni、Michael Campbell、Alan Hudson、Susan A. Charman、Clive Yeates、Ian H. Gilbert

  DOI：10.1021/jm400009c

  日期：2013.4.11

  In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 similar to 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.