4-([1,1'-biphenyl]-4-yl)-1-tosyl-1H-1,2,3-triazole | 1149643-91-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-([1,1'-biphenyl]-4-yl)-1-tosyl-1H-1,2,3-triazole
• 英文别名: 1-(4-Methylphenyl)sulfonyl-4-(4-phenylphenyl)triazole；1-(4-methylphenyl)sulfonyl-4-(4-phenylphenyl)triazole
• CAS: 1149643-91-3
• 化学式: C₂₁H₁₇N₃O₂S
• 分子量: 375.451
• InChiKey: KAAHOOCHTMYGFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-([1,1'-biphenyl]-4-yl)-1-tosyl-1H-1,2,3-triazole 在 辛酸铑 、 水 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以94%的产率得到
  参考文献：
  名称：

  Synthesis of α-Amino Ketones from Terminal Alkynes via Rhodium-Catalyzed Denitrogenative Hydration of N-Sulfonyl-1,2,3-triazoles

  摘要：

  N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce alpha-amino ketones in high yield. An intermediary alpha-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.

  DOI：

  10.1021/ja2104203

文献信息

• The stereoselective synthesis of α-amino aldols starting from terminal alkynes
  作者：Tomoya Miura、Takayuki Nakamuro、Kentaro Hiraga、Masahiro Murakami

  DOI：10.1039/c4cc04786a

  日期：——

  A new procedure for the stereoselective synthesis of syn alpha-amino beta-oxy ketones is reported. It consists of two steps; in the first step, alpha-amino silyl enol ethers having a (Z) geometry are prepared from 1-alkynes via 1-sulfonyl-1,2,3-triazoles. In the second step, the silyl enol ethers undergo the TiCl4-mediated Mukaiyama aldol reaction with aldehydes to produce alpha-amino beta-oxy ketones

  报道了一种立体选择性合成顺式α-氨基β-氧基酮的新方法。它包括两个步骤；在第一步中，通过1-磺酰基-1,2,3-三唑由1-炔烃制备具有（Z）几何形状的α-氨基甲硅烷基烯醇醚。在第二步中，甲硅烷基烯醇醚与醛进行TiCl4介导的Mukaiyama醛醇缩醛反应，以产生具有出色的顺选择性的α-氨基β-氧基酮。
• Highly Efficient Synthesis of N-Sulfonylamidines via Silver-Catalyzed­ or Metal-Free Thermally Promoted Denitrogenative Amination of N-Sulfonyl-1,2,3-triazoles
  作者：Xihe Bi、Xingqi Li、Yue Feng、Wanjia Zhou、Ge Sun、Peiqiu Liao

  DOI：10.1055/s-0036-1588103

  日期：——

  3-triazoles and amines is reported. This transformation undergoes silver-catalyzed or metal-free thermally promoted denitrogenation of N-sulfonyl-1,2,3-triazoles to afford N-sulfonylketenimine intermediates and subsequent nucleophilic addition with amines. The amine plays dual roles as base and nucleophile. A highly efficient synthesis of N-sulfonylamidines from N-sulfonyl-1,2,3-triazoles and amines is reported

  摘要 据报道，由N-磺酰基-1,2,3-三唑和胺可高效合成N-磺酰胺基。该转变经历N-磺酰基-1,2,3-三唑的银催化的或无金属的热促进的脱氮作用，以提供N-磺酰基酮亚胺中间体，并随后与胺进行亲核加成。胺起碱和亲核试剂的双重作用。 据报道，由N-磺酰基-1,2,3-三唑和胺可高效合成N-磺酰胺基。该转变经历N-磺酰基-1,2,3-三唑的银催化的或无金属的热促进的脱氮作用，以提供N-磺酰基酮亚胺中间体，并随后与胺进行亲核加成。胺起碱和亲核试剂的双重作用。
• Tandem O–H Insertion/[1,3]-Alkyl Shift of Rhodium Azavinyl Carbenoids with Benzylic Alcohols: A Route To Convert C–OH Bonds into C–C Bonds
  作者：Pengbing Mi、Rapolu Kiran Kumar、Peiqiu Liao、Xihe Bi

  DOI：10.1021/acs.orglett.6b02459

  日期：2016.10.7

  Alcohols are among the most abundant and commonly used organic feedstock in industrial processes and academic research. The first tandem O–H insertion/[1,3]-alkyl shift reaction reported is between benzylic alcohols and rhodium azavinyl carbenoids derived from N-sulfonyl-1,2,3-triazoles, which provides a strategically novel way of cleaving C–OH bonds and forming C–C bonds. The substrate scope is broad

  酒精是工业过程和学术研究中最丰富，最常用的有机原料之一。报道的第一个串联的O–H插入/ [1,3]-烷基转移反应是在苄醇与衍生自N-磺酰基-1,2,3-三唑的氮杂氮杂乙烯基铑类化合物之间进行的，这提供了一种策略性地裂解C-的新方法。 OH键并形成C–C键。底物的范围很广，能够覆盖1°-，2°-和3°-苄醇。而且，它构成了构造α-氨基酮的新的有力的合成方法。机理研究表明，氧鎓叶立德的[1,3]-烷基移位是C-OH键断裂的原因。
• Synthesis of 2-Substituted 2-Amino Ketones by Rhodium-Catalyzed Reaction of<i>N</i>-Sulfonyl-1,2,3-triazoles with 2-Alkenols
  作者：Tomoya Miura、Takamasa Tanaka、Qiang Zhao、Scott G. Stewart、Masahiro Murakami

  DOI：10.1002/hlca.201600320

  日期：2017.2

  A study on a rhodium(II)‐catalyzed reaction of N‐sulfonyl‐1,2,3‐triazoles with 2‐alkenols is reported. The reaction is initiated by insertion of an α‐imino carbene into the O–H linkage of alcohol, forming a 2‐alkenoxy enamide intermediate. A thermal [3,3]‐sigmatropic rearrangement follows to yield 2‐substituted 2‐amino ketone in a stereoselective manner. The successful application of this methodology

  据报道，铑（II）催化N-磺酰基-1,2,3-三唑与2-烯醇的反应。通过将α-亚氨基卡宾插入醇的OH键中，形成2-烯氧基烯酰胺中间体，从而引发反应。随后发生热[3,3]-σ重排，以立体选择性方式产生2-取代的2-氨基酮。还介绍了该方法在（-）- α- conhydrine形式合成中的成功应用。
• Synthesis of 2,5-diaryloxazoles through rhodium-catalyzed annulation of triazoles and aldehydes
  作者：Jian Li、Shang-Rong Zhu、Yue Xu、Xue-Chen Lu、Zheng-Bing Wang、Li Liu、De-feng Xu

  DOI：10.1039/d0ra03966g

  日期：——

  An efficient synthesis of a variety of 2,5-diaryloxazole derivatives via a rhodium-catalyzed annulation of triazoles and aldehydes is achieved. Various oxazole derivatives could be obtained in good to excellent yields. A concise synthesis of antimycobaterial natural products balsoxin and texamine has been achieved using this method.

  通过铑催化的三唑和醛的环化，实现了多种2,5-二芳基恶唑衍生物的有效合成。可以以良好至优异的收率获得各种恶唑衍生物。利用该方法实现了抗真菌天然产物Balsoxin和Texamine的简洁合成。