4-phenyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)-1H-1,2,3-triazole | 1312680-91-3

• 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-1-((4-(trifluoromethyl)phenyl)sulfonyl)-1H-1,2,3-triazole
• 英文别名: 4-Phenyl-1-[4-(trifluoromethyl)phenyl]sulfonyltriazole
• CAS: 1312680-91-3
• 化学式: C₁₅H₁₀F₃N₃O₂S
• 分子量: 353.325
• InChiKey: ZBLXRKATGJAAJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-phenyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)-1H-1,2,3-triazole 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 作用下， 以 三乙胺 、 苯 为溶剂， 反应 12.5h， 生成 4-phenyl-2-(p-tolylethynyl)-1-((4-(trifluoromethyl)phenyl)sulfonyl)-1H-imidazole
  参考文献：
  名称：

  Synthesis of 2-Bromoimidazoles from Alkynes, N-Sulfonylazides, and Bromocyanides

  摘要：

  A synthetic method for Z-bromoimidazoles is developed from Rh-catalyzed cyclization of N-sulfonyl-1,2,3-triazoles with bromocyanides. Cu-catalyzed [3 + 2] cycloaddition followed by Rh-catalyzed cyclization starting from alkynes, N-sulfonylazides, and bromocyanides is also demonstrated for de novo synthesis of 2-bromoimidazoles in one pot. Moreover, this work was successfully employed to introduce diverse functional groups to the 2-position of imidazoles via cross-coupling reaction.

  DOI：

  10.1021/acs.orglett.5b00977
• 作为产物：
  描述：

  4-三氟甲基苯磺酰氯 在 sodium azide 、 噻吩-2-甲酸亚铜(I) 作用下， 以 水 、 丙酮 、 甲苯 为溶剂， 反应 3.0h， 生成 4-phenyl-1-((4-(trifluoromethyl)phenyl)sulfonyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Catalytic Asymmetric C–H Insertions of Rhodium(II) Azavinyl Carbenes

  摘要：

  A highly efficient enantioselective C-H insertion of azavinyl carbenes into unactivated alkanes has been developed. These transition metal carbenes are directly generated from readily available and stable 1-sulfonyl-1,2,3-triazoles in the presence of chiral Rh(II) carboxylates and are used for C-H functionalization of alkanes to access a variety of beta-chiral sulfonamides.

  DOI：

  10.1021/ja202969z

文献信息

• Sequential Functionalization of the OH and C(<i>sp</i>²)O Bonds of Tropolones by Alkynes and<i>N</i>-Sulfonyl Azides
  作者：Boram Seo、Woo Hyung Jeon、Chul-Eui Kim、Sanghyuck Kim、Sung Hong Kim、Phil Ho Lee

  DOI：10.1002/adsc.201500829

  日期：2016.3.31

  Sequential copper‐catalyzed [3+2] cycloaddition, rhodium‐catalyzed OH insertion, intramolecular 1,8‐addition, and rearrangement starting from 1‐alkynes, N‐sulfonyl azides, and tropolones is demonstrated for the synthesis of the 2‐functionalized aminotropones in one pot. These results indicate that sequential functionalization of OH and C(sp2)O bonds smoothly occurs in the C(sp2)OH bonds of tropolone

  证明了铜催化的[3 + 2]环加成，铑催化的OH插入，分子内的1,8加成和从1-炔烃，N-磺酰叠氮化物和对苯二酚的重排可用于2-酮的合成。一锅中的功能化的氨基tropones。这些结果表明的那顺序官能ö  H和C（SP 2） O键顺利发生在C（SP 2） ø  ħ托酚酮的键
• Synthesis of benzothiazonine by rhodium-catalyzed denitrogenative transannulation of 1-sulfonyl-1,2,3-triazole and thiochromone
  作者：Saygbechi T. Jablasone、Zihang Ye、Shengguo Duan、Ze-Feng Xu、Chuan-Ying Li

  DOI：10.1039/d1ob00419k

  日期：——

  A facile synthesis of functionalized benzothiazonine was achieved by rhodium-catalyzed denitrogenative annulation of easily available 1-sulfonyl-1,2,3-triazole and thiochromone.

  通过铑催化的易得的1-磺酰基-1,2,3-三唑和噻吩醌的脱氮环化反应，成功合成了官能化苯并噻唑啉。
• 연속 흐름 공정을 이용한 설포닐 또는 설파모일 트라이아졸계 화합물의 제조 방법
  申请人：Ewha University - Industry Collaboration Foundation 이화여자대학교 산학협력단(220040083301) BRN ▼110-82-10456

  公开号：KR20190119509A

  公开（公告）日：2019-10-22

  연속 흐름 공정을 이용한 설포닐 또는 설파모일 트라이아졸계 화합물의 제조 방법에 관한 것이다.

  这是关于利用连续流程制备硫代磺酰基或硫代磷아미드三唑类化合物的方法。
• Multicomponent [5 + 2] Cycloaddition Reaction for the Synthesis of 1,4-Diazepines: Isolation and Reactivity of Azomethine Ylides
  作者：Dong Jin Lee、Hong Sik Han、Jinhwan Shin、Eun Jeong Yoo

  DOI：10.1021/ja5061609

  日期：2014.8.20

  Air-stable azomethine ylides with an unusual pattern of charge distribution were efficiently prepared via the rhodium-catalyzed reaction between pyridines and 1-sulfonyl-1,2,3-triazoles. This reaction allowed for the first example of the catalytic multicomponent [5 + 2] cycloaddition reactions, thus resulting in the formation of biologically active 1,4-diazepine compounds.

  通过吡啶和1-磺酰基-1,2,3-三唑之间的铑催化反应有效地制备了具有不寻常电荷分布模式的空气稳定的偶氮甲碱叶立德。该反应允许催化多组分 [5 + 2] 环加成反应的第一个例子，从而导致形成生物活性 1,4-二氮杂化合物。
• Dearomative Migratory Rearrangement of 2-Oxypyridines Enabled by α-Imino Rhodium Carbene
  作者：Guangyang Xu、Ying Shao、Shengbiao Tang、Qun Chen、Jiangtao Sun

  DOI：10.1021/acs.orglett.0c03533

  日期：2020.12.4

  migratory rearrangement reactions of 2-oxypyridines with N-sulfonyl-1,2,3-triazoles have been developed under rhodium catalysis, providing a reliable and efficient protocol for accessing N-substituted 2-pyridones. These two distinct rearrangements feature the controllable 1,4-migration of a carbonate group from O-to-C as well as the O-to-N 1,6-migration of an acyl group via α-imino rhodium carbene transfer

  在铑催化下已经开发了2-氧吡啶与N-磺酰基-1,2,3-三唑的空前的脱芳香族迁移重排反应，为获得N-取代的2-吡啶酮提供了可靠而有效的方案。这两个不同的重排的特征是碳酸酯基团从O到C的可控制的1,4-迁移以及酰基通过α-亚氨基铑卡宾转移而从酰基的O到N的1,6-迁移。此外，吡啶并三唑与2-氧吡啶的反应以高效率递送1，4-迁移产物。