3-(1H-benzo[d]-1,2,3-triazol-1-yl)-1-phenylpropan-1-one | 28918-19-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1H-benzo[d]-1,2,3-triazol-1-yl)-1-phenylpropan-1-one
• 英文别名: 3-(1H-benzo[d][1,2,3]triazol-1-yl)-1-phenylpropan-1-one；3-(benzotriazol-1-yl)propiophenone；3-benzotriazol-1-yl-1-phenyl-propan-1-one；1-(3-Phenyl-3-oxopropyl)-1H-benzotriazol；1-(β-Benzoyl-ethyl)-benzotriazol；1-Benzotriazol-3-phenyl-propan-1-on；3-(Benzotriazol-1-yl)-1-phenylpropan-1-one
• CAS: 28918-19-6
• 化学式: C₁₅H₁₃N₃O
• mdl: MFCD00963695
• 分子量: 251.288
• InChiKey: NBZSZRCZEUQMCL-UHFFFAOYSA-N

物化性质

• 熔点：
  62-63 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  460.9±28.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.133
• 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：

  3-(1H-benzo[d]-1,2,3-triazol-1-yl)-1-phenylpropan-1-one 在 溴 、 sodium acetate 作用下， 以 溶剂黄146 为溶剂， 生成 3-(1H-benzo[d][1,2,3]triazol-1-yl)-2-bromo-1-phenylpropan-1-one
  参考文献：
  名称：

  一些新的1,2,3-苯并三唑衍生物的合成，结构表征和生物学评价

  摘要：

  合成了十种新颖的苯并三唑化合物。通过1 H NMR，IR和元素分析确认了它们的化学结构，以及三个选定的单晶结构（化合物A2，B3和B5）。还研究了它们的抗真菌和抗肿瘤活性。标题化合物显示出一些抗肿瘤活性，尤其是在A3和A4的情况下，它们在肝和半乳癌细胞中显示出最有效的增殖抑制活性。

  DOI：

  10.1007/s00044-009-9243-3
• 作为产物：
  描述：

  T406石油添加剂 、 3-氯代苯丙酮 在 三乙胺 作用下， 以 甲苯 为溶剂， 以82%的产率得到3-(1H-benzo[d]-1,2,3-triazol-1-yl)-1-phenylpropan-1-one
  参考文献：
  名称：

  Design and synthesis of 3-(azol-1-yl)phenylpropanes as microbicidal spermicides for prophylactic contraception

  摘要：

  We designed a series of 25 3-(azol-1-yl)phenylpropanes which yielded 10 compounds (3, 4, 7, 8, 13, 14, 19, 21, 23, 26) that irreversibly immobilized 100% human sperm at 1% (w/v) concentration in 60 s; 12 compounds (8, 9, 15, 16, 19-21, 23-25, 27, 28) that showed potent microbicidal activity at 12.5-50 mu g/mL against Trichomonas vaginalis; and 17 compounds (3-11, 13, 15, 19, 21, 23, 26, 28, 30) that exhibited potent anticandida activity with minimum inhibitory concentration (MIC) of 12.5-50 mu g/mL. Almost all the compounds exhibited high level of safety towards normal vaginal flora (Lactobacillus) and human cervical (HeLa) cells in comparison to the marketed spermicide nonoxynol-9 (N-9). All the biological activities were evaluated in vitro. Two compounds (4, 8) with good safety profile exhibited multiple (spermicidal, antitrichomonas and anticandida) activities, warranting further lead optimization for furnishing a prophylactic vaginal contraceptive. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.11.042

文献信息

• An efficient water-mediated synthetic route for the alkylation of heteroarenes
  作者：Pınar SEYİTDANLIOĞLU、Essam Hamied Ahmed HANASHALSHAHABY、Canan ÜNALEROĞLU

  DOI：10.3906/kim-1802-18

  日期：——

  for the alkylation of 1$H$-indole, 1$H$-benzimidazole, and 1$H$-benzotriazole. This approach features the alkylation of heteroaromatics through in situ generated enones from ketonic Mannich bases under metal-free conditions. A series of alkylated heteroaromatics have been synthesized via the K10 catalyzed alkylation reactions of these heteroaromatics with a variety of ketonic Mannich bases. Environmentally

  已经描述了一种有效的合成路线，用于将1 $ H $-吲哚，1 $ H $-苯并咪唑和1 $ H $-苯并三唑进行烷基化。该方法的特点是在无金属条件下通过酮基曼尼希碱原位生成的烯酮将杂芳烃烷基化。通过这些杂芳族化合物与各种酮基曼尼希碱的K10催化烷基化反应，已经合成了一系列烷基化杂芳族化合物。该烷基化方法的优点是对环境无害的K10催化剂，水介导的温和反应条件以及烷基化产物的有效合成。
• Katritzky, Alan R.; Galuszka, Barbara; Rachwal, Stanislaw, Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 917 - 924
  作者：Katritzky, Alan R.、Galuszka, Barbara、Rachwal, Stanislaw、Black, Michael

  DOI：——

  日期：——
• Design and synthesis of 3-(azol-1-yl)phenylpropanes as microbicidal spermicides for prophylactic contraception
  作者：Lalit Kumar、Amit Sarswat、Nand Lal、Ashish Jain、Sumit Kumar、S.T.V.S. Kiran Kumar、Jagdamba P. Maikhuri、Atindra K. Pandey、Praveen K. Shukla、Gopal Gupta、Vishnu L. Sharma

  DOI：10.1016/j.bmcl.2010.11.042

  日期：2011.1

  We designed a series of 25 3-(azol-1-yl)phenylpropanes which yielded 10 compounds (3, 4, 7, 8, 13, 14, 19, 21, 23, 26) that irreversibly immobilized 100% human sperm at 1% (w/v) concentration in 60 s; 12 compounds (8, 9, 15, 16, 19-21, 23-25, 27, 28) that showed potent microbicidal activity at 12.5-50 mu g/mL against Trichomonas vaginalis; and 17 compounds (3-11, 13, 15, 19, 21, 23, 26, 28, 30) that exhibited potent anticandida activity with minimum inhibitory concentration (MIC) of 12.5-50 mu g/mL. Almost all the compounds exhibited high level of safety towards normal vaginal flora (Lactobacillus) and human cervical (HeLa) cells in comparison to the marketed spermicide nonoxynol-9 (N-9). All the biological activities were evaluated in vitro. Two compounds (4, 8) with good safety profile exhibited multiple (spermicidal, antitrichomonas and anticandida) activities, warranting further lead optimization for furnishing a prophylactic vaginal contraceptive. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, structure characterization, and biological evaluation of some new 1,2,3-benzotriazole derivatives
  作者：Jun Wan、Xia Yan、Cuiping Ma、Sai Bi、Hai-Liang Zhu

  DOI：10.1007/s00044-009-9243-3

  日期：2010.11

  and elemental analyses, coupled with three selected single-crystal structures (compounds A2, B3, and B5). Their antimycotic and antitumor activities were also investigated. The title compounds showed some antitumor activities, especially in the case of A3 and A4, which showed the most potent activity of propagation inhibition in liver and galactophore cancer cells.

  合成了十种新颖的苯并三唑化合物。通过1 H NMR，IR和元素分析确认了它们的化学结构，以及三个选定的单晶结构（化合物A2，B3和B5）。还研究了它们的抗真菌和抗肿瘤活性。标题化合物显示出一些抗肿瘤活性，尤其是在A3和A4的情况下，它们在肝和半乳癌细胞中显示出最有效的增殖抑制活性。