1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)propen-1-one | 99736-86-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)propen-1-one
• 英文别名: 1-phenyl-2-(1H-1,2,4-triazolo-yl)-3-phenyl-prop-en-1-one；1,3-diphenyl-2-[1,2,4]triazol-1-yl-propenone；1,3-diphenyl-2-(1,2,4-triazolyl)-propenone；1,3-Diphenyl-2-(1h-1,2,4-triazol-1-yl)propen-1-one；1,3-diphenyl-2-(1,2,4-triazol-1-yl)prop-2-en-1-one
• CAS: 99736-86-4
• 化学式: C₁₇H₁₃N₃O
• 分子量: 275.31
• InChiKey: AMSRANWZOYZEKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)propen-1-one 在 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 96.0h， 生成 2-(((1Z,2E)-1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)allylidene)amino)phenyl (Z)-N-hydroxy-4-methoxybenzimidothioate
  参考文献：
  名称：

  Investigation on the Ring-Opening Reactions of 3-(1H-1,2,4-Triazol-1-yl)1,5-benzothiazepines with Arylonitrile Oxides

  摘要：

  Novel ring opening compounds, (Z)-2-((Z)-((E)-1,3-diaryl-2-(1H-1,2,4-triazol-1-yl)allylidene)amino)aryl N-hydroxybenzimidothioates 4a-r, were obtained from the reaction of 2,4-diaryl-3-(1H-1,2,4-triazol-1-yl)-2,5-dihydro-1,5-benzothiazepines 3a-f and arylonitrile oxides. The structure of these products has been elucidated by spectroscopic analysis and, in one case, X-ray crystallographic analysis. According to the result, it was presumed that this reaction did not proceeded through 1,3-dipolar cycloaddition reaction.

  DOI：

  10.1080/10426507.2010.509290
• 作为产物：
  描述：

  2-溴苯乙酮 在 哌啶 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)propen-1-one
  参考文献：
  名称：

  Synthesis and Crystal Structure of Compound 1-Phenyl-2-(1H-1,2,4-triazolo-yl)-3-phenyl-propen-1-one and 1-Diphenyl-3-(1,2,4-triazolo-yl)-1H,4H-1,5-benzothiazepine

  摘要：

  化合物的晶体结构 1-苯基-2-(1H-1,2,4-三唑基)-3-苯基-丙烯-1-酮 (2) 和 2,4-二苯基-3-(1通过单晶X射线衍射得到了2,4-三唑基)-1H,4H-1,5-苯并硫氮杂卓(3)。化合物 2 在三斜晶系中结晶，空间群为 P − 1，a = 8.5553(17) Å，b = 9.6229(19) Å，c = 9.924(2) Å，α = 106.16(3)°，β = 108.03( 3)°, γ = 105.14(3)°, V = 690.1(2) Å3, Z = 2。化合物 3 为斜方晶系结晶，空间群为 Pbca，a = 12.904(3) Å, b = 15.864(3) ) Å, c = 19.140(4) Å, α = 90°, β = 90°, γ = 90°, V = 3918.3(14) Å3, Z = 8。氢键和 π-π 堆积是主要的非键-分子结构中的键合相互作用。讨论了这两种化合物的合成、结构和光谱性质的细节。化合物的晶体结构 1-苯基-2-(1H-1,2,4-三唑基)-3-苯基-丙烯-1-酮 (2) 和 2,4-二苯基-3-(1通过单晶X射线衍射得到了2,4-三唑基)-1H,4H-1,5-苯并硫氮杂卓(3)。化合物 2 在三斜晶系中结晶，空间群为 P − 1，a = 8.5553(17) Å，b = 9.6229(19) Å，c = 9.924(2) Å，α = 106.16(3)°，β = 108.03( 3)°, γ = 105.14(3)°, V = 690.1(2) Å3, Z = 2。化合物 3 为斜方晶系结晶，空间群为 Pbca，a = 12.904(3) Å, b = 15.864(3) ) Å, c = 19.140(4) Å, α = 90°, β = 90°, γ = 90°, V = 3918.3(14) Å3, Z = 8。氢键和 π-π 堆积是主要的非键-分子结构中的键合相互作用。讨论了这两种化合物的合成、结构和光谱性质的细节。

  DOI：

  10.1007/s10870-010-9906-4

文献信息

• Synthesis and Crystal Structure of Compound 1-Phenyl-2-(1H-1,2,4-triazolo-yl)-3-phenyl-propen-1-one and 1-Diphenyl-3-(1,2,4-triazolo-yl)-1H,4H-1,5-benzothiazepine
  作者：Sheng-Qin Chen、Fang-Ming Liu

  DOI：10.1007/s10870-010-9906-4

  日期：2011.4

  The crystal structures of the compounds 1-phenyl-2-(1H-1,2,4-triazolo-yl)-3-phenyl-propen-1-one (2), and 2,4-diphenyl-3-(1,2,4-triazolo-yl)-1H,4H-1,5-benzothiazepine (3) were obtained by single crystal X-ray diffraction. Compound 2 crystallizes in the triclinic system with space group P − 1, a = 8.5553(17) Å, b = 9.6229(19) Å, c = 9.924(2) Å, α = 106.16(3)°, β = 108.03(3)°, γ = 105.14(3)°, V = 690.1(2) Å3, Z = 2. The compound 3 crystallizes in the orthorhombic system with space group Pbca, a = 12.904(3) Å, b = 15.864(3) Å, c = 19.140(4) Å, α = 90°, β = 90°, γ = 90°, V = 3918.3(14) Å3, Z = 8. H-bonds and π–π stacking are the main non-bonding interactions in the molecular structure. Details of the synthesis, structures, and spectroscopic properties of the two compounds are discussed. The crystal structures of the compounds 1-phenyl-2-(1H-1,2,4-triazolo-yl)-3-phenyl-propen-1-one (2), and 2,4-diphenyl-3-(1,2,4-triazolo-yl)-1H,4H-1,5-benzothiazepine (3) were obtained by single crystal X-ray diffraction. Compound 2 crystallizes in the triclinic system with space group P − 1, a = 8.5553(17) Å, b = 9.6229(19) Å, c = 9.924(2) Å, α = 106.16(3)°, β = 108.03(3)°, γ = 105.14(3)°, V = 690.1(2) Å3, Z = 2. The compound 3 crystallizes in the orthorhombic system with space group Pbca, a = 12.904(3) Å, b = 15.864(3) Å, c = 19.140(4) Å, α = 90°, β = 90°, γ = 90°, V = 3918.3(14) Å3, Z = 8. H-bonds and π–π stacking are the main non-bonding interactions in the molecular structure. Details of the synthesis, structures, and spectroscopic properties of the two compounds are discussed.

  化合物的晶体结构 1-苯基-2-(1H-1,2,4-三唑基)-3-苯基-丙烯-1-酮 (2) 和 2,4-二苯基-3-(1通过单晶X射线衍射得到了2,4-三唑基)-1H,4H-1,5-苯并硫氮杂卓(3)。化合物 2 在三斜晶系中结晶，空间群为 P − 1，a = 8.5553(17) Å，b = 9.6229(19) Å，c = 9.924(2) Å，α = 106.16(3)°，β = 108.03( 3)°, γ = 105.14(3)°, V = 690.1(2) Å3, Z = 2。化合物 3 为斜方晶系结晶，空间群为 Pbca，a = 12.904(3) Å, b = 15.864(3) ) Å, c = 19.140(4) Å, α = 90°, β = 90°, γ = 90°, V = 3918.3(14) Å3, Z = 8。氢键和 π-π 堆积是主要的非键-分子结构中的键合相互作用。讨论了这两种化合物的合成、结构和光谱性质的细节。化合物的晶体结构 1-苯基-2-(1H-1,2,4-三唑基)-3-苯基-丙烯-1-酮 (2) 和 2,4-二苯基-3-(1通过单晶X射线衍射得到了2,4-三唑基)-1H,4H-1,5-苯并硫氮杂卓(3)。化合物 2 在三斜晶系中结晶，空间群为 P − 1，a = 8.5553(17) Å，b = 9.6229(19) Å，c = 9.924(2) Å，α = 106.16(3)°，β = 108.03( 3)°, γ = 105.14(3)°, V = 690.1(2) Å3, Z = 2。化合物 3 为斜方晶系结晶，空间群为 Pbca，a = 12.904(3) Å, b = 15.864(3) ) Å, c = 19.140(4) Å, α = 90°, β = 90°, γ = 90°, V = 3918.3(14) Å3, Z = 8。氢键和 π-π 堆积是主要的非键-分子结构中的键合相互作用。讨论了这两种化合物的合成、结构和光谱性质的细节。
• Structural Characterization of New Compound from the Ring-Opening Reaction of 3-(1H-1,2,4-triazol-1-yl)-1,5-Benzothiazepine with Phenylonitrile Oxide
  作者：Sheng-Qin Chen、Fei Ding、Yi-Chao Zhang、Fang-Ming Liu

  DOI：10.1007/s10870-010-9911-7

  日期：2011.4

  The crystal structure of the product (Z)-2-((Z)-((Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)allylidene)amino)phenyl N-hydroxybenzimidothioate (4) was obtained by single crystal X-ray diffraction. The title compound, C30H23N5OS (4), crystallizes in the triclinic space group, P-1, with unit cell parameters a = 8.3306(17) Å, b = 11.394(2) Å, c = 14.560(3) Å, α = 78.75(3)º, β = 89.96(3)º, γ = 70.56(3)º, Z = 2. In the crystal structure, adjacent molecules are linked by O–H···N hydrogen bonds. H-bonds and π–π stacking are the main non-bonding interactions in the molecular structure and give support to molecular packing stability. In addition, the structure is supported by a weak intermolecular C–H···Cg π-ring interaction. Detail of the synthesis, structures, and spectroscopic properties of the title compound is discussed. The crystal structure of the product (Z)-2-((Z)-((Z)-1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl)allylidene)amino)phenyl N-hydroxybenzimidothioate (4) was obtained by single crystal X-ray diffraction. The title compound, C30H23N5OS (4), crystallizes in the triclinic space group, P-1, with unit cell parameters a = 8.3306(17) Å, b = 11.394(2) Å, c = 14.560(3) Å, α = 78.75(3)º, β = 89.96(3)º, γ = 70.56(3)º, Z = 2. In the crystal structure, adjacent molecules are linked by O–H···N hydrogen bonds. H-bonds and π–π stacking are the main non-bonding interactions in the molecular structure and give support to molecular packing stability. In addition, the structure is supported by a weak intermolecular C–H···Cg π-ring interaction. Detail of the synthesis, structures, and spectroscopic properties of the title compound is discussed.

  通过单晶 X 射线衍射获得了 (Z)-2-((Z)-((Z)-1,3-二苯基-2-(1H-1,2,4-三唑-1-基)烯丙基亚甲基)氨基)苯基 N-羟基硫代苯并咪唑盐（4）的晶体结构。标题化合物 C30H23N5OS (4) 结晶于三linic 空间群 P-1，单胞参数 a = 8.3306(17) Å, b = 11.394(2) Å, c = 14.在晶体结构中，相邻分子通过 O-H-N 氢键相连。H 键和π-π堆叠是分子结构中主要的非键相互作用，为分子堆积的稳定性提供了支持。此外，分子间还存在微弱的 C-H-Cg π环相互作用。本文详细讨论了标题化合物的合成、结构和光谱特性。通过单晶 X 射线衍射获得了产物 (Z)-2-((Z)-((Z)-1,3-二苯基-2-(1H-1,2,4-三唑-1-基)烯丙基亚甲基)氨基)苯基 N-羟基硫代苯并咪唑盐 (4) 的晶体结构。标题化合物 C30H23N5OS (4) 结晶于三linic 空间群 P-1，单胞参数 a = 8.3306(17) Å, b = 11.394(2) Å, c = 14.在晶体结构中，相邻分子通过 O-H-N 氢键相连。H 键和π-π堆叠是分子结构中主要的非键相互作用，为分子堆积的稳定性提供了支持。此外，分子间还存在微弱的 C-H-Cg π环相互作用。本文详细讨论了标题化合物的合成、结构和光谱特性。
• Synthesis and Fungicidal Activity of 5-Aryl-1-(aryloxyacetyl)-3-(<i>tert</i>-butyl or phenyl)-4-(1<i>H</i>-1,2,4-triazol-1-yl)-4,5-dihydropyrazole
  作者：Hui-Yu Mao、Hong Song、De-Qing Shi

  DOI：10.1002/jhet.934

  日期：2013.3

  A series of novel 5‐aryl‐1‐(aryloxyacetyl)‐3‐(tert‐butyl or phenyl)‐4‐(1H‐1,2,4‐triazol‐1‐yl)‐4,5‐dihydropyrazole 3a–3n were synthesized by the annulation of 2‐aryloxyacetohydrazides with 3‐aryl‐1‐t‐butyl (or phenyl)‐2‐(1H‐1,2,4‐triazol‐1‐yl)prop‐2‐en‐1‐ones (2) in the presence of a catalytic amount of acetic acid. Compounds 2 were obtained by the Knoevenagel reactions of 1‐t‐butyl (or phenyl)‐2‐(1H‐1,2,4‐triazol‐1‐yl)ethanone (1) with aromatic aldehydes in the presence of piperidine. Their structures were confirmed by IR, 1H‐NMR, ESI‐MS, and elemental analyses. The preliminary bioassay indicated that some compounds displayed moderate to excellent fungicidal activity. For example, compounds 3l, 3m, and 3n possessed 100% inhibition against Cercospora arachidicola Hori at the concentration of 50 mg/L.
• Investigation on the Ring-Opening Reactions of 3-(1H-1,2,4-Triazol-1-yl)1,5-benzothiazepines with Arylonitrile Oxides
  作者：Sheng-Qin Chen、Fei Ding、Fang-Ming Liu

  DOI：10.1080/10426507.2010.509290

  日期：2011.2.28

  Novel ring opening compounds, (Z)-2-((Z)-((E)-1,3-diaryl-2-(1H-1,2,4-triazol-1-yl)allylidene)amino)aryl N-hydroxybenzimidothioates 4a-r, were obtained from the reaction of 2,4-diaryl-3-(1H-1,2,4-triazol-1-yl)-2,5-dihydro-1,5-benzothiazepines 3a-f and arylonitrile oxides. The structure of these products has been elucidated by spectroscopic analysis and, in one case, X-ray crystallographic analysis. According to the result, it was presumed that this reaction did not proceeded through 1,3-dipolar cycloaddition reaction.
• Synthesis and crystal structure of isoxazoline derivatives bearing a 1,2,4-triazole moiety
  作者：Zhi-Qiang Dong、Fang-Ming Liu、Sheng-Qin Chen

  DOI：10.1007/s00706-012-0722-8

  日期：2012.11

  AbstractNovel isoxazoline derivatives bearing a 1,2,4-triazole moiety have been synthesized starting from 2-bromo-1-phenylethanone. Chalcones were obtained by aldol condensation of 1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanone and 4-substituted benzaldehydes using piperidine as catalyst. Finally, 1,3-dipolar cycloaddition of the chalcones and a variety of aldoximes in the presence of chloramine-T afforded

  摘要从2-溴-1-苯基乙酮开始合成了带有1,2,4-三唑部分的新型异恶唑啉衍生物。使用哌啶作为催化剂，通过1-苯基-2-（1 H -1,2,4-三唑-1-基）乙酮与4-取代的苯甲醛的醛醇缩合制得Chalcones 。最后，在氯胺-T存在下，查耳酮和各种醛肟的1，3-偶极环加成反应得到标题化合物。根据红外光谱，核磁共振，质谱和元素分析数据，以及对新型异恶唑啉类似物的典型实例进行X射线分析，证实了这些化合物的结构特征。 图形概要