5-bromo-1-phenyl-1H-1,2,4-triazole | 21434-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-bromo-1-phenyl-1H-1,2,4-triazole
• 英文别名: 5-bromo-1-phenyl-1H-[1,2,4]triazole；5-Brom-1-phenyl-1,2,4-triazol；Brom-5-phenyl-1-triazol-1,2,4；5-bromo-1-phenyl-1,2,4-triazole
• CAS: 21434-15-1
• 化学式: C₈H₆BrN₃
• 分子量: 224.06
• InChiKey: VVKRUJQGEZCXRQ-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  355.4±25.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromo-1-phenyl-1H-1,2,4-triazole 在 四(三苯基膦)钯 、 silica gel 作用下， 以 乙醚 、 正己烷 、 苯 为溶剂， 反应 18.0h， 生成 (E)-3-(2-Phenyl-2H-[1,2,4]triazol-3-yl)-propenal
  参考文献：
  名称：

  1-三丁基锡烷基-3,3-二乙氧基丙-1-烯作为ad 3丙烯醛的当量

  摘要：

  1-三丁基锡烷基-3,3-二乙氧基丙-1-烯已被证明是易于获得的β-甲酰基乙烯基阴离子当量，在温和的实验条件下，该化合物可轻松接触肉桂酸酯骨架和4-氧代或6-氧代-α，β-灌肠。

  DOI：

  10.1039/p19900000187
• 作为产物：
  描述：

  1-苯基-1H-1,2,4-噻唑 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 12.0h， 以80%的产率得到5-bromo-1-phenyl-1H-1,2,4-triazole
  参考文献：
  名称：

  Synthesis and Antitumor Activity of 1,5-Disubstituted 1,2,4-Triazoles as Cis-Restricted Combretastatin Analogues

  摘要：

  A series of 1-aryl-5-(3',4',5'-trimethoxyphenyl) derivatives and their related 1-(3',4',5'-trimethoxyphenyl)5-aryl-1,2,4-triazoles, designed as cis-restricted combretastatin analogues, were synthesized and evaluated for antiproliferative activity, inhibitory effects on tubulin polymerization, cell cycle effects, and apoptosis induction. Their activity was greater than, or comparable with, that of the reference compound CA-4. Flow cytometry studies showed that HeLa and Jurkat cells treated with the most active compounds 4l and 4o were arrested in the G2/M phase of the cell cycle in a concentration dependent manner. This effect was accompanied by apoptosis of the cells, mitochondrial depolarization, generation of reactive oxygen species, activation of caspase-3, and PA RP cleavage. Compound 41 was also shown to have potential antivascular activity, since it induced endothelial cell shape change in vitro and disrupted the sprouting of endothelial cells in the chick aortic ring assay.

  DOI：

  10.1021/jm100245q

文献信息

• Substituent and coordination effects in singlet reactions of 3-diazo-3H-1,2,4-triazoles with substituted benzenes and nitro compounds
  作者：J Glinka、D Fiscus、C.B Rao、H Shechter

  DOI：10.1016/s0040-4039(00)95476-5

  日期：1987.1

  3-Diazo-3-1,2,4-triazoles convert to singlet 3-1,2,4-triazol-3-ylidenes which (1) effect directed electrophilic substitutions of benzenes and (2) coordinate with benzenoid substituents and nitro compounds to give decomposition or rearrangement products.

  3-重氮-3-2,1,2,4-三唑转化为单线态3,1,2,4-三唑-3-亚烷基，其（1）影响苯的亲电取代，以及（2）与苯并基取代基和硝基化合物配位给出分解或重排产物。
• In Situ Generation and Trapping of Aryllithium and Arylpotassium Species by Halogen, Sulfur, and Carbon Electrophiles
  作者：Ilya Popov、Hien-Quang Do、Olafs Daugulis

  DOI：10.1021/jo9015369

  日期：2009.11.6

  A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene Pentafluorobenzene, benzothiazole,and benzoxazole can be functionalized by using K3PO4 base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pK(a) values of 35 or less are reactive.
• PARRAIN, JEAN-LUC;DUCHENE, ALAIN;QUINTARD, JEAN-PAUL, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 187-189
  作者：PARRAIN, JEAN-LUC、DUCHENE, ALAIN、QUINTARD, JEAN-PAUL

  DOI：——

  日期：——
• [EN] NEW BROMODOMAIN INHIBITORS<br/>[FR] NOUVEAUX INHIBITEURS DE BROMODOMAINES
  申请人：ORION CORP

  公开号：WO2018109271A1

  公开（公告）日：2018-06-21

  The present invention provides novel spiro[cycloalkyl-1,3'-indolin]-2'-one derivatives of formula (I), in which Cy1,Cy2,R1,R2, R3,R4, L,m, n and q have the meaning given in the specification, and pharmaceutically acceptable salts thereof. The compounds of formula (I) are useful as bromodomain inhibitors in the treatment or prevention of diseases or disorders where bromodomain inhibition is desired.
• 1-Tributylstannyl-3,3-diethoxyprop-1 -ene as a d³acrolein equivalent
  作者：Jean-Luc Parrain、Alain Duchêne、Jean-Paul Quintard

  DOI：10.1039/p19900000187

  日期：——

  1-Tributylstannyl-3,3-diethoxyprop-1-ene has proved to be a readily available β-formylvinyl anion equivalent which under mild experimental conditions gives ready access to cinnamic skeletons and 4-oxo- or 6-oxo-α,β-enals.

  1-三丁基锡烷基-3,3-二乙氧基丙-1-烯已被证明是易于获得的β-甲酰基乙烯基阴离子当量，在温和的实验条件下，该化合物可轻松接触肉桂酸酯骨架和4-氧代或6-氧代-α，β-灌肠。