1-benzyl-4-tosyl-1H-1,2,3-triazole | 1178886-35-5

• 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: 1-benzyl-4-tosyl-1H-1,2,3-triazole
• 英文别名: 1-Benzyl-4-(4-methylphenyl)sulfonyltriazole；1-benzyl-4-(4-methylphenyl)sulfonyltriazole
• CAS: 1178886-35-5
• 化学式: C₁₆H₁₅N₃O₂S
• 分子量: 313.38
• InChiKey: JXLJREPEKXPSOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-benzyl-4-tosyl-1H-1,2,3-triazole 在 四甲基氯化铵 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)–1,2,3-Triazole Carbene Complexes

  摘要：

  New and well-characterized Ag-bis(1,2,3-triazolylidene) complexes having enantiopure (S)-sulfoxides upon sequential sequential treatment with alcohols and Au(I) form separable mixtures of regioisomeric C-unsubstituted Au-1,2,3-triazolylidene complexes. Mechanistic studies and DFT calculations support a desulfinylation process for in situ generated free triazolylidene salts.

  DOI：

  10.1021/acs.orglett.6b03808
• 作为产物：
  描述：

  1-(ethynylsulfinyl)-4-methylbenzene 在 copper(ll) sulfate pentahydrate 、 四甲基氯化铵 、 sodium ascorbate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 25.0h， 生成 1-benzyl-4-tosyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)–1,2,3-Triazole Carbene Complexes

  摘要：

  New and well-characterized Ag-bis(1,2,3-triazolylidene) complexes having enantiopure (S)-sulfoxides upon sequential sequential treatment with alcohols and Au(I) form separable mixtures of regioisomeric C-unsubstituted Au-1,2,3-triazolylidene complexes. Mechanistic studies and DFT calculations support a desulfinylation process for in situ generated free triazolylidene salts.

  DOI：

  10.1021/acs.orglett.6b03808

文献信息

• Regioselectivity of the 1,3-Dipolar Cycloaddition of Organic Azides to 7-Heteronorbornadienes. Synthesis of β-Substituted Furans/Pyrroles
  作者：Enrique Gil de Montes、Macarena Martı́nez-Bailén、Ana T. Carmona、Inmaculada Robina、Antonio J. Moreno-Vargas

  DOI：10.1021/acs.joc.0c00810

  日期：2020.7.17

  efficient procedure for the preparation of β-substituted furans/pyrroles is presented. The methodology is based on the use of 7-oxa/azanorbornadienes as dipolarophiles in 1,3-dipolar cycloaddition with benzyl azide. The triazoline cycloadduct thus formed spontaneously decomposes via a retro-Diels–Alder (rDA) reaction to afford a β-substituted furan/pyrrole derivative and a stable triazole. The scope of this

  提出了制备β-取代的呋喃/吡咯的有效方法。该方法基于在叠氮化苄与1,3-偶极环加成中使用7-氧杂/氮杂降冰片二烯作为亲极亲和性。如此形成的三唑啉环加合物通过逆Diels-Alder（rDA）反应自发分解，得到β-取代的呋喃/吡咯衍生物和稳定的三唑。用13种7-杂二降冰片二烯研究了串联1,3-偶极环加成/ rDA反应的范围。这项研究使人们对反应的区域选择性有了深入的了解，可以通过异降冰片二烯体系的取代基进行调节。
• A Procedure for Fast and Regioselective Copper-Free Click Chemistry at Room Temperature with <i>p</i>-Toluenesulfonyl Alkyne
  作者：Sébastien Gouin、José Kovensky

  DOI：10.1055/s-0029-1216744

  日期：——

  Sulfonyl alkyne group can undergo copper-free cyclization at room temperature with diverse azido compounds. In solvent-free conditions the reaction was fast, yielding 1,4-disubstituted ­regioisomers with high regioselectivity.

  磺酰炔基团可以在室温下与多种叠氮基化合物进行无铜环化。在无溶剂条件下，反应速度很快，产生具有高区域选择性的 1,4-二取代区域异构体。
• Selective Formation of 1,4-Disubstituted Triazoles from Ruthenium-Catalyzed Cycloaddition of Terminal Alkynes and Organic Azides: Scope and Reaction Mechanism
  作者：Pei Nian Liu、Juan Li、Fu Hai Su、Kun Dong Ju、Li Zhang、Chuan Shi、Herman H. Y. Sung、Ian D. Williams、Valery V. Fokin、Zhenyang Lin、Guochen Jia

  DOI：10.1021/om300513w

  日期：2012.7.9

  The catalytic activity of a series of ruthenium complexes lacking cyclopentadienyl ligands has been evaluated for the cycloaddition of terminal alkynes and azides to give selectively 1,4-disubstituted 1,2,3-triazoles. The complex RuH(eta(2)-BH4)(CO)(PCy3)(2) was found to be an effective catalyst for the cycloaddition reactions. In the presence of RuH(eta(2)-BH4)(CO)(PCy3)(2), primary and secondary azides reacted with a range of terminal alkynes containing various functionalities to selectively produce 1,4-disubstituted 1,2,3-triazoles. The ruthenium-catalyzed azide-alkyne cycloaddition appears to proceed via a Ru-acetylide species as the key intermediate, which undergoes formal cycloaddition with an azide to give a ruthenium triazolide complex. The 1,4-disubstituted 1,2,3-triazole product is generated by metathesis of the triazolide complex with a terminal alkyne. In support of the reaction mechanism, the acetylide complex Ru(C CCMe3)(2)(CO)(PPh3)(3) reacts cleanly with benzyl azide to give a ruthenium triazolide complex, which reacts with excess tert-butylacetylene in the presence of PPh3 to give 4-tert-butyl-1-benzyl-1,2,3-triazole and the diacetylide complex Ru(C CCMe3)(2)(CO)(PPh3)(3). The mechanism is also supported by DFT calculations.