4-phenyl-5-(1-phenylvinyl)-2H-1,2,3-triazole | 1186338-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-phenyl-5-(1-phenylvinyl)-2H-1,2,3-triazole
• 英文别名: 4-phenyl-5-(1-phenylethenyl)-2H-triazole
• CAS: 1186338-98-6
• 化学式: C₁₆H₁₃N₃
• 分子量: 247.299
• InChiKey: IZDGRIDSSHGKMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-phenyl-5-(1-phenylvinyl)-2H-1,2,3-triazole 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以100%的产率得到4-phenyl-5-(1-phenylethyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  One Step Cascade Synthesis of 4,5-Disubstituted-1,2,3-(NH)-Triazoles

  摘要：

  A Lewis base-catalyzed three-component cascade reaction was developed for the synthesis of 4,5-disubstituted-1,2,3-(NH)-triazoles. More than 25 new (NH)-triazoles were prepared in good to excellent yields under mild conditions. The availability of the C-4 vinyl group allows easy conversion into other triazole derivatives.

  DOI：

  10.1021/ol8002783
• 作为产物：
  描述：

  (E)-1-nitro-2-phenyl-1-propene 、 苯甲醛 在 sodium azide 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以89%的产率得到4-phenyl-5-(1-phenylvinyl)-2H-1,2,3-triazole
  参考文献：
  名称：

  One Step Cascade Synthesis of 4,5-Disubstituted-1,2,3-(NH)-Triazoles

  摘要：

  A Lewis base-catalyzed three-component cascade reaction was developed for the synthesis of 4,5-disubstituted-1,2,3-(NH)-triazoles. More than 25 new (NH)-triazoles were prepared in good to excellent yields under mild conditions. The availability of the C-4 vinyl group allows easy conversion into other triazole derivatives.

  DOI：

  10.1021/ol8002783

文献信息

• Mitsunobu Reaction of 1,2,3-NH-Triazoles: A Regio- and Stereoselective Approach to Functionalized Triazole Derivatives
  作者：Wuming Yan、Tao Liao、Odbadrakh Tuguldur、Cheng Zhong、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1002/asia.201100357

  日期：2011.10.4

  The Mitsunobu reaction was used in the preparation of chiral triazole derivatives. The reactions gave good to excellent yields with large substrate scope. Complete stereochemistry inversion was obtained, making this strategy one practical approach for the synthesis of enantiomeric enriched triazole analogous.

  Mitsunobu反应用于制备手性三唑衍生物。该反应在较大的底物范围内产生了良好的优异产率。获得了完全的立体化学转化，使得该策略成为合成对映体富集的三唑类似物的一种实用方法。
• Conformational control in the regioselective synthesis of N-2-substituted-1,2,3-triazoles
  作者：Yunfeng Chen、Yuxiu Liu、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1039/b805328f

  日期：——

  An effective strategy for the synthesis of N-2-substituted-1,2,3-triazoles with excellent yields and regioselectivity has been developed.

  已开发出具有优异产率和区域选择性的合成N-2-取代-1,2,3-三唑的有效策略。
• Facile synthesis and stereo-resolution of chiral 1,2,3-triazoles
  作者：Ye Shi、Xiaohan Ye、Qiang Gu、Xiaodong Shi、Zhiguang Song

  DOI：10.1039/c5ob00479a

  日期：——

  triazoles were used as starting materials, followed by sequential epoxidation, rearrangement and reduction to give the corresponding hydroxyl-triazoles. The CalB lipase catalyzed kinetic resolution gave enantiomerically pure (>99% ee) chiral triazoles in excellent yield. These new chiral TAs were also successfully applied as ligands in asymmetric addition of diethylzinc to aldehydes.

  我们在本文中描述了通过侧链官能化的手性三唑的第一种简便的合成方法。使用现成的C-乙烯基三唑作为起始原料，然后依次环氧化，重排和还原，得到相应的羟基三唑。CalB脂肪酶催化的动力学拆分以优异的收率得到对映体纯的（> 99％ee）手性三唑。这些新的手性TAs还成功地用作二乙基锌不对称加成到醛中的配体。
• Efficient Synthesis of <i>N</i>-2-Aryl-1,2,3-Triazole Fluorophores via Post-Triazole Arylation
  作者：Yuxiu Liu、Wuming Yan、Yunfeng Chen、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1021/ol802246q

  日期：2008.12.4

  Efficient post-triazole regloselective N-2 arylation was developed from C-4, C-5 disubstituted-1,2,3-NH-triazoles. Three different approaches had been investigated, including SNAr, Cu(I) catalyzed aryl amidation and Cu(II) mediated boronic acid coupling. The N-2-aryl triazoles were successfully synthesized with excellent yields. The structures were characterized by X-ray crystallography and some N-2-triazole products gave strong fluorescence with various emission controlled by the C-5 groups.
• Highly efficient synthesis of vinyl substituted triazoles by Au(I) catalyzed alkyne activation
  作者：Haifeng Duan、Wuming Yan、Sujata Sengupta、Xiaodong Shi

  DOI：10.1016/j.bmcl.2009.03.096

  日期：2009.7

  Au(I) catalyzed 1,2,3-triazole addition to non-activated alkyne was reported. A large group of substituted NH-1,2,3-triazoles were suitable for this transformation along with both internal and terminal alkynes. The N-1 and N-2 vinyl substituted 1,2,3-triazoles were prepared in up to 98% yield with as low as 0.2% catalyst loading, thereby providing a new protocol for the synthesis of potentially biological-active vinyl-triazole building blocks. (C) 2009 Elsevier Ltd. All rights reserved.