3-Azido-1-phenyl-1-cyclohexene

• 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: 3-Azido-1-phenyl-1-cyclohexene
• 英文别名: 5-azido-2,3,4,5-tetrahydro-1,1'-biphenyl；5-azido-2,3,4,5-tetrahydro-1,1′-biphenyl；1-azido-3-phenyl-2-cyclohexene；(3-Azidocyclohexen-1-yl)benzene
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: YRFAAZMZTOUEFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Azido-1-phenyl-1-cyclohexene 以 neat (no solvent) 为溶剂， 反应 25.0h， 生成 N-(3-phenylcyclohex-2-enyl)benzamide
  参考文献：
  名称：

  Chemoselectivity in Coupling of Azides with Thioacids in Solution-Phase and Solvent-Free Conditions

  摘要：

  Solvent-free rapid coupling of monothiocarboxylic acid with azide affords carboxamide chemoselectively. Triphenyl phosphine included as an additive influences the chemoselectivity, yielding carboxamide and thioamide. Similar variation in the chemoselectivity is observed in the absence and presence of triphenyl phosphine in solution-phase methodology. Rapidity and ecofriendliness of the solvent-free approach to yield the products in just 15 min is noteworthy compared to the solution-phase protocol, which has a long reaction time (1-3 days).

  DOI：

  10.1080/00397911.2011.606043
• 作为产物：
  描述：

  3-phenyl-cyclohex-2-enol 在 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 苯 为溶剂， 反应 24.0h， 以52%的产率得到3-Azido-1-phenyl-1-cyclohexene
  参考文献：
  名称：

  Structure of the IN3 adduct of 1-phenylcyclohexane. Its chemistry and CH coupling as a diagnostic tool

  摘要：

  DOI：

  10.1021/jo00294a051

文献信息

• A Cascade Reaction of Cinnamyl Azides with Acrylates Directly Generates Tetrahydro-Pyrrolo-Pyrazole Heterocycles
  作者：Angela S. Carlson、En-Chih Liu、Joseph J. Topczewski

  DOI：10.1021/acs.joc.0c00535

  日期：2020.5.1

  Developing reactions to generate complex and modular building blocks in a concise and direct fashion remains a contemporary synthetic challenge. This work describes a stereoselective cascade reaction between allylic azides and acrylates that directly generates tetrahydro-pyrrolo-pyrazole ring systems. These products contain up to four contiguous stereocenters, two of which may be tetrasubstituted carbon

  发展反应以简洁，直接的方式生成复杂的模块化构建模块仍然是当代的综合挑战。这项工作描述了烯丙基叠氮化物和丙烯酸酯之间的立体选择性级联反应，该反应直接生成四氢-吡咯并-吡唑环系统。这些产物包含多达四个连续的立体中心，其中两个可以是连接至氮原子的四取代的碳原子。提供了30多个示例，平均分离产率为71％（范围从40％到94％）。该反应易于规模化以使用多于一克的起始原料，并且产物可以容易地多样化。
• Evidence for a Sigmatropic and an Ionic Pathway in the Winstein Rearrangement
  作者：Amy A. Ott、Mary H. Packard、Manuel A. Ortuño、Alayna Johnson、Victoria P. Suding、Christopher J. Cramer、Joseph J. Topczewski

  DOI：10.1021/acs.joc.8b00961

  日期：2018.8.3

  The spontaneous rearrangement of allylic azides is thought to be a sigmatropic reaction. Presented herein is a detailed investigation into the rearrangement of several allylic azides. A combination of experiments including equilibrium studies, kinetic analysis, density functional theory calculations, and selective 15N-isotopic labeling are included. We conclude that the Winstein rearrangement occurs

  烯丙基叠氮化物的自发重排被认为是σ反应。本文提出了对几种烯丙基叠氮化物的重排的详细研究。包括平衡研究，动力学分析，密度泛函理论计算和选择性15 N同位素标记在内的实验组合。我们得出的结论是，在大多数情况下，Winstein重排都是通过假定的σ路径发生的。但是，观察到某些环状烯丙基叠氮化物的消旋化。提供了对该过程的动力学分析，其支持了先前未描述的离子途径。
• Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis
  作者：Poovan Shanmugavelan、Sangaraiah Nagarajan、Murugan Sathishkumar、Alagusundaram Ponnuswamy、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmcl.2011.10.048

  日期：2011.12

  Efficient and rapid synthesis of 1,2,3-triazole derivatives has been achieved via Huisgen's 1,3-dipolar cycloaddition between alkyl/arylazides and diethyl/dimethyl acetylenedicarboxylate in excellent yields under solvent-free conditions. The environmentally friendly solvent-free protocol overcomes the limitations associated with the prevailing time-consuming solution phase protocols and affords the triazoles just in 1-3 min. In vitro antitubercular activity of these triazoles was screened against Mycobacterium tuberculosis H(37)Rv strain. Four of the compounds showed MIC in the range of 1.56-3.13 mu g/mL proving their potential activity. (C) 2011 Elsevier Ltd. All rights reserved.
• Murugan, Sathish Kumar; Sangaraiah, Nagarajan; Velan, Poovan Shanmuga, Journal of the Brazilian Chemical Society, 2011, vol. 22, # 11, p. 2065 - 2069
  作者：Murugan, Sathish Kumar、Sangaraiah, Nagarajan、Velan, Poovan Shanmuga、Murugan, Dinesh、Ponnuswamy, Alagusundaram

  DOI：——

  日期：——
• Solvent-free protocol for amide bond formation via trapping of nascent phosphazenes with carboxylic acids
  作者：Murugan Sathishkumar、Poovan Shanmugavelan、Sangaraiah Nagarajan、Murugesan Maheswari、Murugan Dinesh、Alagusundaram Ponnuswamy

  DOI：10.1016/j.tetlet.2011.03.069

  日期：2011.6

  A solvent-free synthesis of amides via the coupling of phosphazenes with carboxylic acids is reported. Increasing the rate of heating either by microwave irradiation or conventional heating results in multifold increase in the rate of amide bond formation. Synthesis of a library of amides including a potent antitumour candidate has been accomplished. (C) 2011 Elsevier Ltd. All rights reserved.