3-(1H-1,2,4-噻唑-1-基)-丙酸甲酯 | 106535-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(1H-1,2,4-噻唑-1-基)-丙酸甲酯
• 英文名称: 3-[1,2,4]triazol-1-yl-propionic acid methyl ester
• 英文别名: methyl 3-(1,2,4-triazol-1-yl)propionate；1-methylpropionatotriazole；methyl 3-(1H-1,2,4-triazol-1-yl)propanoate；methyl 3-(1,2,4-triazol-1-yl)propanoate
• CAS: 106535-19-7
• 化学式: C₆H₉N₃O₂
• mdl: MFCD07367969
• 分子量: 155.156
• InChiKey: PVTDBXDIDCTVFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1H-1,2,4-噻唑-1-基)-丙酸甲酯 、 肼 以31%的产率得到
  参考文献：
  名称：

  DALLACKER, F.;MINN, K., CHEM.-ZTG, 1986, 110, N 3, 101-108

  摘要：

  DOI：
• 作为产物：
  描述：

  1H-1,2,4-三唑 、 丙烯酸甲酯（MA） 在 potassium phosphate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以92%的产率得到3-(1H-1,2,4-噻唑-1-基)-丙酸甲酯
  参考文献：
  名称：

  使用无水 K3PO4 作为催化剂将 N-杂环迈克尔加成到 α,β-不饱和化合物的温和有效程序

  摘要：

  咪唑、1,2,4-三唑、吲哚和苯并三唑在无水磷酸钾的存在下在环境温度下与 ,-不饱和羰基化合物进行共轭加成，以优异的产率得到相应的迈克尔加合物。

  DOI：

  10.1080/00397910903029867

文献信息

• A fast and highly efficient protocol for Michael addition of N-heterocycles to α,β-unsaturated compound using basic ionic liquid [bmIm]OH as catalyst and green solvent
  作者：Jian-Ming Xu、Chao Qian、Bo-Kai Liu、Qi Wu、Xian-Fu Lin

  DOI：10.1016/j.tet.2006.11.013

  日期：2007.1

  A fast and green protocol for the Michael addition of N-heterocycles to α,β-unsaturated compounds at room temperature was developed using a basic ionic liquid, 1-methyl-3-butylimidazolium hydroxide, [bmIm]OH, as a catalyst and a reaction medium. The reactions were performed at room temperature with good yields in short reaction times (0.5–3 h). This strategy is quite general and it works with a broad

  使用碱性离子液体1-甲基-3-丁基咪唑鎓氢氧化物[bmIm] OH作为催化剂，并使用碱性离子液体，开发了一种快速，绿色的方法，用于在室温下将N-杂环迈克尔加成至α，β-不饱和化合物。反应介质。反应在室温下以短的反应时间（0.5–3小时）以良好的收率进行。该策略是相当普遍的，并且适用于广泛的N-杂环，包括五元N-杂环，嘧啶和嘌呤。回收的离子液体可重复使用几个循环，具有一致的活性。
• Solvent- and Catalyst-Free Aza-Michael Addition of Imidazoles and Related Heterocycles
  作者：Katharina Kodolitsch、Florian Gobec、Christian Slugovc

  DOI：10.1002/ejoc.202000309

  日期：2020.5.22

  The completely solvent free as well as catalyst free aza‐Michael addition reaction of azoles to liquid Michael acceptors is studied. As long as the solubility of the azole in the reaction mixture is sufficient, the addition reaction proceeds towards completion in several hours at 80 °C as has been demonstrated with 12 examples.

  研究了吡咯与液态迈克尔受体的完全无溶剂以及无催化剂的氮杂-迈克尔加成反应。只要唑在反应混合物中的溶解度足够，加成反应就可以在80℃在数小时内完成，如用1​​2个实施例所证明的。
• <i>N</i>-Methylimidazole as a Promising Catalyst for the Aza-Michael Addition Reaction of N-Heterocycles
  作者：Xian Lin、Bo Liu、Qi Wu、Xue Qian、De Lv

  DOI：10.1055/s-2007-983816

  日期：2007.9

  N-Methylimidazole has been shown to be a promising catalyst for aza-Michael reactions. Various N-heterocycles were introduced­ to α,β-unsaturated carbonyl compounds employing N-meth­ylimidazole (0.05 equiv) in a highly efficient, rapid and high yielding synthesis of N-heterocyclic derivatives.

  N-甲基咪唑已被证明是一种有前景的用于aza-Michael反应的催化剂。利用N-甲基咪唑（0.05 equiv），在高度高效、快速且高产率的合成过程中，将各种N-杂环引入到α,β-不饱和羰基化合物中，生成了N-杂环衍生物。
• Fused azole-thiazolines <i>via</i> one-pot cyclization of functionalized N-heterocyclic carbene precursors
  作者：Qiaoqiao Teng、Chandan Singh、Yuan Han、Han Vinh Huynh

  DOI：10.1039/c9ob02548k

  日期：——

  Various bi/tricyclic azole-thiazolines are obtained via a new one-pot protocol from cheap starting materials.

  通过一种新的一锅法，可以从廉价的起始材料中获得各种双/三环唑-噻唑烯。
• Promiscuous acylase-catalyzed aza-Michael additions of aromatic N-heterocycles in organic solvent
  作者：Chao Qian、Jian-Ming Xu、Qi Wu、De-Shui Lv、Xian-Fu Lin

  DOI：10.1016/j.tetlet.2007.06.164

  日期：2007.8

  A novel and efficient enzymatic promiscuous protocol for aza-Michael addition of aromatic N-heterocycles to alpha,beta-unsaturated compounds has been described. The reactions were catalyzed by promiscuous zinc-active-site acylase in organic solvent at 50 degrees C. The strategy works with a broad range of N-heterocycles to afford the corresponding Michael adduct with good yields in several hours (0.5-6 h). This catalytic promiscuity is the first example of metal-active-site enzyme-catalyzed aza-Michael addition for aromatic N-heterocycles. (c) 2007 Elsevier Ltd. All rights reserved.