1-(4-Methylphenyl)-3-methoxycarbonyl-5-hydroxymethyl-4,5-dihydropyrazole

• 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: 1-(4-Methylphenyl)-3-methoxycarbonyl-5-hydroxymethyl-4,5-dihydropyrazole
• 英文别名: Methyl 3-(hydroxymethyl)-2-(4-methylphenyl)-3,4-dihydropyrazole-5-carboxylate
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: ADFNTZNIYNBADS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 2-chloro-2-(4-methylphenyl-hydrazono)acetate 、 烯丙醇 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.1h， 以18%的产率得到1-(4-Methylphenyl)-3-methoxycarbonyl-5-hydroxymethyl-4,5-dihydropyrazole
  参考文献：
  名称：

  Nitrilimine cycloadditions in aqueous media

  摘要：

  研究人员首次在水介质中对多种烯基二亲极性化合物进行了氮基亚胺基环加成反应。观察到的环化结果明显取决于多个因素，包括二极亲和物的电子特征和在水中的溶解度，以及反应混合物中是否存在阳离子表面活性剂或有机助溶剂。

  DOI：

  10.1039/b005567k

文献信息

• A Short and Convenient Synthesis of Novel Thienopyrazolodiazepine and Thienopyrazoloxazepine Skeletons via Nitrilimine Cycloaddition
  作者：Giorgio Molteni、Paola Del Buttero

  DOI：10.3987/com-10-11905

  日期：——

  generation of the corresponding nitrilimine (4) which constitute the key intermediate in the three step synthesis of both thieno[2,3-f]pyrazolo[1,5-a][1,4]diazepine and thieno[2,3-Apyrazolo[1,5-a][1,4]- oxazepine skeletons. The concurrent formation of unusual pyridazine derivatives arising from the electrophilic attack of a nitrilium cation to the carbon-carbon double bond is also discussed in some

  碳酸银处理 3-噻吩基取代的肼酰氯 (3) 促进了相应的腈亚胺 (4) 的原位生成，该腈亚胺 (4) 是噻吩并[2,3-f]吡唑并[1, 5-a][1,4] 二氮杂和噻吩并[2,3-Apyrazolo[1,5-a][1,4]- oxazep​​ine 骨架。还详细讨论了由腈阳离子对碳-碳双键的亲电攻击引起的不寻常哒嗪衍生物的同时形成。
• Oxygenated monoterpenes as dipolarophiles for nitrilimine cycloadditions
  作者：Lara De Benassuti、Luisa Garanti、Giorgio Molteni

  DOI：10.1016/j.tet.2004.03.077

  日期：2004.5

  A variety of naturally-occurring oxygenated monoterpenes, namely (S)-cis-verbenol, (1R)-(-)-myternol, (1S)-(-)-verbenone, (1R)-(-)-myternal, (S)-(-)-perillyl alcohol, and (S)-(-)-perillaldehyde have been submitted to nitrilimine cycloaddition. These processes were fully regio- and stereoselective for four dipolarophiles. In contrast, regioselective but non-stereoselective cycloadditions occurred in the case of two of the monoterpene derivatives. The configurations of the newly-formed stereocentres of the cycloadducts were assigned on the basis of NOE and NOESY experiments. (C) 2004 Elsevier Ltd. All rights reserved.