甲基4-氰基-1-甲基-1H-吡咯-2-羧酸酯 | 40740-43-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 甲基4-氰基-1-甲基-1H-吡咯-2-羧酸酯
• 英文名称: methyl 4-cyano-1-methyl-pyrrole-2-carboxylate
• 英文别名: 1-Methyl-4-cyano-2-pyrrolcarbonsaeuremethylester；4-cyano-1-methyl-pyrrole-2-carboxylic acid methyl ester；Methyl 4-cyano-1-methyl-1H-pyrrole-2-carboxylate；methyl 4-cyano-1-methylpyrrole-2-carboxylate
• CAS: 40740-43-0
• 化学式: C₈H₈N₂O₂
• 分子量: 164.164
• InChiKey: HQBXXDPQBFVNEF-UHFFFAOYSA-N

物化性质

• 沸点：
  287.3±25.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基4-氰基-1-甲基-1H-吡咯-2-羧酸酯 在 甲醇 、 氢氧化钾 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 4-cyano-1-methyl-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Structure–activity relationship and liver microsome stability studies of pyrrole necroptosis inhibitors

  摘要：

  Necroptosis is a regulated caspase-independent cell death pathway resulting in morphology reminiscent of passive nonregulated necrosis. Several diverse structure classes of necroptosis inhibitors have been reported to date, including a series of [1,2,3] thiadiazole benzylamide derivatives. However, initial evaluation of mouse liver microsome stability indicated that this series of compounds was rapidly degraded. A structure-activity relationship (SAR) study of the [1,2,3] thiadiazole benzylamide series revealed that increased mouse liver microsome stability and increased necroptosis inhibitory activity could be accomplished by replacement of the 4-cyclopropyl-[1,2,3] thiadiazole with a 5-cyano-1-methylpyrrole. In addition, the SAR and the cellular activity profiles, utilizing different cell types and necroptosis-inducing stimuli, of representative [1,2,3] thiadiazole and pyrrole derivatives were very similar suggesting that the two compound series inhibit necroptosis in the same manner. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.048
• 作为产物：
  描述：

  zinc(II) cyanide 、 4-溴-1-甲基-1H-吡咯-2-羧酸甲酯 在 [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 18.0h， 以89%的产率得到甲基4-氰基-1-甲基-1H-吡咯-2-羧酸酯
  参考文献：
  名称：

  水介质中（杂）芳基卤化物和三氟甲磺酸酯的轻度钯催化氰化

  摘要：

  据报道，轻度，有效和低温钯催化的（杂）芳基卤化物和三氟甲磺酸酯的氰化反应。先前钯催化的（杂）芳基卤化物的氰化需要更高的温度以实现良好的催化活性。该当前反应可以使一般范围的（杂）芳基卤化物和三氟甲磺酸酯在催化剂负载量为2％至5％的条件下从rt到40°C进行氰化。这种温和的方法适用于逆转录酶抑制剂lersivirine的合成。

  DOI：

  10.1021/ol5032359

文献信息

• Ligand-Promoted Rosenmund–von Braun Reaction
  作者：Dawei Ma、Quan Zhang

  DOI：10.1055/s-0042-1751414

  日期：——

  accelerating effect to classical Rosenmund–von Braun reaction, making the coupling of (hetero)aryl bromides with CuCN occur at 100–120 °C with good to excellent yields in most cases. A large number of functional groups and heterocycles were tolerated under these conditions, thereby providing a convenient and reliable approach for diverse synthesis of aryl nitriles.

  发现两种吡啶甲酰胺配体对经典的 Rosenmund-von Braun 反应具有显着的加速作用，使得（杂）芳基溴化物与 CuCN 的偶联发生在 100-120 °C，在大多数情况下具有良好至优异的产率。在这些条件下可以容忍大量的官能团和杂环，从而为芳基腈的多样化合成提供了一种方便可靠的方法。
• Mild Palladium-Catalyzed Cyanation of (Hetero)aryl Halides and Triflates in Aqueous Media
  作者：Daniel T. Cohen、Stephen L. Buchwald

  DOI：10.1021/ol5032359

  日期：2015.1.16

  A mild, efficient, and low-temperature palladium-catalyzed cyanation of (hetero)aryl halides and triflates is reported. Previous palladium-catalyzed cyanations of (hetero)aryl halides have required higher temperatures to achieve good catalytic activity. This current reaction allows the cyanation of a general scope of (hetero)aryl halides and triflates at 2–5 mol % catalyst loadings with temperatures

  据报道，轻度，有效和低温钯催化的（杂）芳基卤化物和三氟甲磺酸酯的氰化反应。先前钯催化的（杂）芳基卤化物的氰化需要更高的温度以实现良好的催化活性。该当前反应可以使一般范围的（杂）芳基卤化物和三氟甲磺酸酯在催化剂负载量为2％至5％的条件下从rt到40°C进行氰化。这种温和的方法适用于逆转录酶抑制剂lersivirine的合成。
• Structure–activity relationship and liver microsome stability studies of pyrrole necroptosis inhibitors
  作者：Xin Teng、Heather Keys、Junying Yuan、Alexei Degterev、Gregory D. Cuny

  DOI：10.1016/j.bmcl.2008.04.048

  日期：2008.6

  Necroptosis is a regulated caspase-independent cell death pathway resulting in morphology reminiscent of passive nonregulated necrosis. Several diverse structure classes of necroptosis inhibitors have been reported to date, including a series of [1,2,3] thiadiazole benzylamide derivatives. However, initial evaluation of mouse liver microsome stability indicated that this series of compounds was rapidly degraded. A structure-activity relationship (SAR) study of the [1,2,3] thiadiazole benzylamide series revealed that increased mouse liver microsome stability and increased necroptosis inhibitory activity could be accomplished by replacement of the 4-cyclopropyl-[1,2,3] thiadiazole with a 5-cyano-1-methylpyrrole. In addition, the SAR and the cellular activity profiles, utilizing different cell types and necroptosis-inducing stimuli, of representative [1,2,3] thiadiazole and pyrrole derivatives were very similar suggesting that the two compound series inhibit necroptosis in the same manner. (C) 2008 Elsevier Ltd. All rights reserved.