ethyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylate | 214541-34-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylate
• 英文别名: ethyl 1-(4-methoxyphenyl)triazole-4-carboxylate
• CAS: 214541-34-1
• 化学式: C₁₂H₁₃N₃O₃
• 分子量: 247.254
• InChiKey: NDCOVVHHHRNCCX-UHFFFAOYSA-N

物化性质

• 熔点：
  113-115 °C
• 沸点：
  400.7±51.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylate 在 盐酸 、 水 作用下， 生成 1-(4-methoxyphenyl)-1H-[1,2,3]-triazolyl-4-carboxylic acid
  参考文献：
  名称：

  Synthesis of aminoquinolones from triazoles via carboxamidoketenimine and amidinoketene intermediates

  摘要：

  1 芳基-1H-1,2,3-三唑-4-甲酰胺 7d-f 已被合成，并通过闪速真空热解（FVT）转化为 2-二甲基氨基-4-喹啉酮 12d-f。反应通过羧酰胺基乙烯亚胺 9 和脒基乙烯中间体 10 进行。前者可在 77 K 或 12 K 的氩基质中通过傅立叶变换红外光谱观察到。

  DOI：

  10.1039/a802768d
• 作为产物：
  描述：

  甲氧苯胺 在 盐酸 、 bathophenanthrolinedispufonic acid disodium salt 、 copper(II) sulfate 、 sodium ascorbate 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and Structure–Activity Relationship Studies of Conformationally Flexible Tetrahydroisoquinolinyl Triazole Carboxamide and Triazole Substituted Benzamide Analogues as σ₂ Receptor Ligands

  摘要：

  Two novel classes of compounds targeting the sigma-2 (sigma(2)) receptor were synthesized, and their bioactivities to binding sigma(1) and sigma(2) receptors were measured. Four novel triazole carboxamide analogues, 24d, 24e, 24f, and 39c, demonstrated high affinity and selectivity for the sigma(2) receptor. These data suggest C-11-labeled versions of these compounds may be potential sigma(2)-selective radiotracers for imaging the proliferative status of solid tumors.

  DOI：

  10.1021/jm5001453

文献信息

• Heterogeneous Copper Catalyst for the Cycloaddition of Azides and Alkynes without Additives under Ambient Conditions
  作者：In Soo Park、Min Serk Kwon、Youngkwon Kim、Jae Sung Lee、Jaiwook Park

  DOI：10.1021/ol702790w

  日期：2008.2.1

  A new copper catalyst was developed by immobilizing copper nanoparticles in aluminum oxyhydoxide fiber. The catalyst showed high catalytic activity for the (3+2) Huisgen cycloaddition of nonactivated alkynes as well as activated ones with various azides at room temperature. The catalyst was recycled five times without significant loss of activity.

  通过将铜纳米颗粒固定在氢氧化铝中开发了一种新的铜催化剂。该催化剂在室温下对未活化炔烃的（3 + 2）Huisgen环加成反应以及与各种叠氮化物活化的炔烃表现出高催化活性。催化剂被循环五次而没有明显的活性损失。
• 4 β -amidotriazole linked podophyllotoxin congeners: DNA topoisomerase-IIα inhibition and potential anticancer agents for prostate cancer
  作者：V. Ganga Reddy、Srinivasa Reddy Bonam、T. Srinivasa Reddy、Ravikumar Akunuri、V.G.M. Naidu、V. Lakshma Nayak、Suresh K. Bhargava、H.M. Sampath Kumar、P. Srihari、Ahmed Kamal

  DOI：10.1016/j.ejmech.2017.12.050

  日期：2018.1

  and topo-II) have occupied a significant role in DNA replication, transcription, and are a promising set of antitumor targets. In the present approach, a series of new 4β-amidotriazole linked podophyllotoxin derivatives (10a-i and 11a-k) were designed, synthesized by employing the click chemistry and their biological activities were evaluated. The majority of derivatives showed promising antiproliferative

  拓扑异构酶（topo-I和topo-II）在DNA复制，转录中起着重要作用，并且是一组有希望的抗肿瘤靶标。在本方法中，一系列新的4个β -amidotriazole联鬼臼毒素衍生物（10A-I和图11A-K ）被设计，通过采用点击化学和它们的生物活性进行了评价合成。大多数衍生物在六种人类癌细胞系上显示出令人鼓舞的抗增殖活性，IC 50值范围为1至10μM。宫颈（HeLa），乳腺（MCF-7），前列腺（DU-145），肺（A549），肝（HepG2）和结肠（HT-29）。其中一些同类物10b，10g和10i已显示出显着的细胞毒性，对测试的癌细胞系的IC 50值<1μM，并且比依托泊苷具有更高的活性。拓扑异构酶介导的DNA弛豫试验结果表明，该衍生物能有效抑制拓扑异构酶II的活性。此外，对DU-145细胞的流式细胞仪分析表明，这些化合物可阻止细胞周期的G2 / M期。还对这些DU-145细胞进行
• Heterogeneous Copper Nanocatalyst and Manufacturing Methods Thereof
  申请人：Park Jai Wook

  公开号：US20110172417A1

  公开（公告）日：2011-07-14

  This invention relates to a heterogeneous copper nanocatalyst composed of copper nanoparticles immobilized on a boehmite support, a method of preparing the same, and the use thereof. The copper nanocatalyst composed of the copper nanoparticles supported on boehmite exhibits excellent performance in a Huisgen cycloaddition reaction and an A3 coupling reaction of aldehyde, amine and alkyne. The copper nanocatalyst is able to be prepared in a large scale and shows superior reactivity even when used in a small amount under mild conditions without an additive in an organic reaction. This heterogeneous catalyst is easy to separate and reuse after the reaction.

  本发明涉及一种异质铜纳米催化剂，由铜纳米颗粒固定在氧化铝支撑物上组成，以及其制备方法和使用方法。铜纳米颗粒支撑在氧化铝上的铜纳米催化剂在Huisgen环加成反应和醛、胺和炔的A3偶联反应中表现出优异的性能。铜纳米催化剂能够在大规模下制备，并且即使在有机反应中在温和条件下无添加剂时，使用少量也表现出优异的反应活性。这种异质催化剂易于在反应后分离和重复使用。
• Alkyl Propiolates Participated [3+2] Annulation for the Switchable Synthesis of 1,5‐ and 1,4‐Disubstituted 1,2,3‐Triazoles Containing Ester Side Chain
  作者：Shuo Cao、Yunyun Liu、Changfeng Hu、Chengping Wen、Jie‐Ping Wan

  DOI：10.1002/cctc.201801366

  日期：2018.11.7

  By means of a featured enamine activation, the alkyl propiolates have been successfully employed in the [3+2] annulation for the synthesis of 1,2,3‐triazoles. The synthesis of both 1,4‐ as well as the hardly available 1,5‐disubstituted 1,2,3‐triazoles can be selectively accessed by using tosyl azide and tosyl hydrazine as nitrogen source, respectively.

  通过特征性的烯胺活化，丙酸烷基酯已成功用于[3 + 2]环合中，用于合成1,2,3-三唑。通过分别使用甲苯磺酰甲苯磺酰基和甲苯磺酰肼作为氮源，可以选择性地获得1,4-以及几乎不可用的1,5-二取代的1,2,3-三唑的合成。
• JP2011527628A
  申请人：——

  公开号：JP2011527628A

  公开（公告）日：2011-11-04