1-(1-p-chlorophenyl-1H-1,2,3-triazol-4-yl)ethanone | 117111-05-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(1-p-chlorophenyl-1H-1,2,3-triazol-4-yl)ethanone
• 英文别名: 1-[1-(4-Chlorophenyl)triazol-4-yl]ethanone
• CAS: 117111-05-4
• 化学式: C₁₀H₈ClN₃O
• 分子量: 221.646
• InChiKey: PYGZEHDILWEXHH-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  381.4±48.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-p-chlorophenyl-1H-1,2,3-triazol-4-yl)ethanone 在 盐酸羟胺 、 溴 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 1-(1-p-chlorophenyl-1H-1,2,3-triazol-4-yl)-2-bromoethanone oxime
  参考文献：
  名称：

  Hetero-Diels-Alder reactions of novel 3-triazolyl-nitrosoalkenes as an approach to functionalized 1,2,3-triazoles with antibacterial profile

  摘要：

  The generation and reactivity of 3-triazolyl-nitrosoalkenes are reported for the first time. The study showed that hetero-Diels-Alder reaction of these heterodienes is an interesting synthetic strategy to functionalized 1,2,3-triazoles, including 1,2,3-triazolyl-pyrroles, 1,2,3-triazolyl-dipyrromethanes and 1,2,3-triazolyl-indoles. The evaluation of the antibacterial profile against Gram-positive and Gramnegative strains revealed the new 5,5'-diethyldipyrromethane bearing a side chain incorporating a triazole and oxime moieties. The antibacterial profile detected was within the Clinical and Laboratory Standard Institute (CLSI) range and against important Staphylococcus species including Methicillin-resistant strain (S. aureus ATCC 25923, S. epidermidis ATCC 12228 and S. simulans ATCC 27851 and MRSA). Interestingly, this new 1,2,3-triazole presented hemocompatibility and low in silico toxicity profile similar to antibiotics current in use. It also has an usual antibiofilm activity against MRSA, which reinforced its potential as a new antibacterial prototype. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.052
• 作为产物：
  描述：

  1-叠氮-4-氯苯 在 sodium dichromate 、 copper(ll) sulfate pentahydrate 、 硫酸 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 24.5h， 生成 1-(1-p-chlorophenyl-1H-1,2,3-triazol-4-yl)ethanone
  参考文献：
  名称：

  Hetero-Diels-Alder reactions of novel 3-triazolyl-nitrosoalkenes as an approach to functionalized 1,2,3-triazoles with antibacterial profile

  摘要：

  The generation and reactivity of 3-triazolyl-nitrosoalkenes are reported for the first time. The study showed that hetero-Diels-Alder reaction of these heterodienes is an interesting synthetic strategy to functionalized 1,2,3-triazoles, including 1,2,3-triazolyl-pyrroles, 1,2,3-triazolyl-dipyrromethanes and 1,2,3-triazolyl-indoles. The evaluation of the antibacterial profile against Gram-positive and Gramnegative strains revealed the new 5,5'-diethyldipyrromethane bearing a side chain incorporating a triazole and oxime moieties. The antibacterial profile detected was within the Clinical and Laboratory Standard Institute (CLSI) range and against important Staphylococcus species including Methicillin-resistant strain (S. aureus ATCC 25923, S. epidermidis ATCC 12228 and S. simulans ATCC 27851 and MRSA). Interestingly, this new 1,2,3-triazole presented hemocompatibility and low in silico toxicity profile similar to antibiotics current in use. It also has an usual antibiofilm activity against MRSA, which reinforced its potential as a new antibacterial prototype. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.11.052

文献信息

• Reactivity of Steroidal 1-Azadienes toward Carbonyl Compounds under Enamine Catalysis: Chiral Penta- and Hexacyclic Steroids
  作者：Susana M. M. Lopes、Clara S. B. Gomes、Teresa M. V. D. Pinho e Melo

  DOI：10.1021/acs.orglett.8b01783

  日期：2018.7.20

  reactivity of a steroidal N-sulfonyl-1-azadiene, derived from 16-dehydropregnenolone acetate, toward carbonyl compounds under enamine catalysis is disclosed. An unexpected annulation reaction was observed involving an initial stereoselective conjugate addition of the in situ generated enamine to the steroidal 1-azadiene. The developed diastereoselective synthetic methodology is a novel approach to a

  公开了在烯胺催化下衍生自16-脱氢孕烯醇酮乙酸酯的甾族N-磺酰基-1-氮杂二烯对羰基化合物的合成和反应性。观察到意外的环状反应，涉及将原位产生的烯胺最初立体选择性共轭加成到甾族1-氮杂二烯。发达的非对映选择性合成方法是一种新的方法，用于处理一类新的手性五环和六环类固醇。
• On the mechanochemical synthesis of C-scorpionates with an oxime moiety and their application in the copper-catalyzed azide–alkyne cycloaddition (CuAAC) reaction
  作者：Carla Gomes、Mariana Costa、Susana M. M. Lopes、Bernardo Albuquerque Nogueira、Rui Fausto、José A. Paixão、Teresa M. V. D. Pinho e Melo、Luísa M. D. R. S. Martins、Marta Pineiro

  DOI：10.1039/d3nj05017c

  日期：——

  substituent at the C-center. The new catalysts were used to efficiently catalyze azide–alkyne cycloaddition reactions under solvent-free mechanochemical conditions. Through the overall process, we combine atom economy, the use of safer solvents and auxiliaries, design for energy efficiency and reduction of derivatives and catalysis (the 1st, 5th, 6th, 8th, and 9th principles of Green Chemistry). The sustainability

  可持续工艺的发展需要整合绿色化学原理。在这项工作中，我们开发了由吡唑和卤代肟通过1,4-加成到球磨下原位生成的共轭α-卤代亚硝基烯烃上无溶剂合成双-和三-(吡唑-1-基)甲烷的方法。使用无溶剂程序和等摩尔量的反应物，将前配体与铜络合，得到在 C 中心具有肟取代基的催化剂 C-蝎形铜 (II)。新型催化剂用于在无溶剂机械化学条件下有效催化叠氮-炔环加成反应。在整个过程中，我们将原子经济性、更安全的溶剂和助剂的使用、能源效率设计以及衍生物和催化的减少（绿色化学的第一、第五、第六、第八和第九原则）结合起来。可持续性指标表明，机械化学为催化剂的制备和铜催化叠氮化物-炔环加成（CuAAC）反应提供了一种更环保、更可持续的方法。新型C-蝎子酸盐及其金属配合物的开发，以及它们随后在机械化学条件下的CuAAC反应中的应用，为可持续点击化学的未来提供了令人兴奋的途径。
• Benati, Luisa; Montevecchi, Pier Carlo; Toselli, Maurizio, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1859 - 1864
  作者：Benati, Luisa、Montevecchi, Pier Carlo、Toselli, Maurizio、Spagnolo, Piero

  DOI：——

  日期：——
• BENATI, LUISA;MONTEVECCHI, PIER CARLO;TOSELLI, MAURIZIO;SPAGNOLO, PIERO, J. CHEM. SOC. PERKIN TRANS. PT 1,(1988) N, C. 1859-1863
  作者：BENATI, LUISA、MONTEVECCHI, PIER CARLO、TOSELLI, MAURIZIO、SPAGNOLO, PIERO

  DOI：——

  日期：——
• BENATI, LUISA;MONTEVECCHI, P. CARLO;SPAGNOLO, PIERO, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N2, C. 2235-2243
  作者：BENATI, LUISA、MONTEVECCHI, P. CARLO、SPAGNOLO, PIERO

  DOI：——

  日期：——