3-(1H-benzo[d][1,2,3]triazol-1-yl)cyclohexanone | 132287-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 3-(1H-benzo[d][1,2,3]triazol-1-yl)cyclohexanone
• 英文别名: 3-(Benzotriazol-1-yl)cyclohexan-1-one
• CAS: 132287-04-8
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: TWULTBILQSJVMB-UHFFFAOYSA-N

物化性质

• 沸点：
  423.1±38.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  47.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  T406石油添加剂 、 2-环己烯-1-酮 以 水 为溶剂， 60.0 ℃ 、600.01 MPa 条件下， 反应 20.0h， 以96%的产率得到3-(1H-benzo[d][1,2,3]triazol-1-yl)cyclohexanone
  参考文献：
  名称：

  氮杂环与水中烯酮的高压促进非催化氮杂-迈克尔反应的新方法

  摘要：

  描述了一种新的绿色化学方法，用于在高压条件下不使用任何催化剂的水作为溶剂中氮杂环与烯酮的氮杂-迈克尔反应。

  DOI：

  10.1055/s-2008-1072594

文献信息

• <scp>Aza‐Michael</scp> addition of 1, <scp>2‐diazoles</scp> to structurally diverse enones: Efficient methods toward <scp>β‐amino</scp> ketones
  作者：Saibabu Polina、V. P. Rama Kishore Putta、Raghuram Gujjarappa、Prasad Pralhad Pujar、Chandi C. Malakar

  DOI：10.1002/jhet.4221

  日期：2021.4

  An efficient and mild protocol was realized using 1,2‐diazoles and related heterocycles with cyclic and acyclic enones in presence of T3P (2,4,6‐tripropyl‐1,3,5,2,4,6‐trioxatriphosphorinane‐2,4,6‐trioxide) toward the regioselective formation of N‐cycloalkyl heterocycles at room temperature. The developed reaction conditions showcased good selectivity over a wide range of 1,2‐diazoles and enones by

  在存在T3P（2,4,6-三丙基-1,3,5,2,4,6-三氧三磷酸正膦2， 4,6-三氧化物）在室温下朝向N-环烷基杂环的区域选择性形成。发达的反应条件通过以极高的产率提供N-环烷基杂环，在1,2-二唑和烯酮中显示出良好的选择性。
• Organocatalytic Enantioselective aza-Michael Additions of N-Heterocycles to α,β-Unsaturated Enones
  作者：Jian Lv、Hao Wu、Yongmei Wang

  DOI：10.1002/ejoc.200901227

  日期：2010.4

  A procedure for enantioselective organocatalytic conjugate additions of a variety of N-heterocycles to α,β-unsaturated enone systems is presented. The reactions are efficiently catalyzed by salts of 9-amino-9-deoxy-epiquinine (3d). Cyclic, acyclic, and aromatic enones can be used in reactions with 1H-benzotriazole (1a) or 5-phenyltetrazole derivatives 12, providing the Michael addition products in

  介绍了将各种 N-杂环对映选择性有机催化共轭加成到 α,β-不饱和烯酮系统的过程。该反应由 9-氨基-9-脱氧-表奎宁 (3d) 的盐有效催化。环状、无环和芳族烯酮可用于与 1H-苯并三唑 (1a) 或 5-苯基四唑衍生物 12 的反应，以高产率提供迈克尔加成产物，并具有良好的对映选择性。
• Uncatalysed intermolecular aza-Michael reactions
  作者：Florian Medina、Nathalie Duhal、Christophe Michon、Francine Agbossou-Niedercorn

  DOI：10.1016/j.crci.2012.11.001

  日期：2013.4

  Résumé The catalyst-free reactions of activated alkenes with primary and secondary amines were investigated leading to various mono- and di-hydroamination products, the latter being rare and original. These reactions were shown to depend first on the strength of the nucleophile. Temperature and steric hindrance of the reagents were the other key factors controlling the selectivity of these aza-Michael reactions. In spite of their poor nucleophilicities, some N-heterocyclic amines could react with different activated alkenes affording valuable intermediates. Such results tended to demonstrate the hydrogen-bonding interactions between activated alkenes and poly-nitrogen aromatic cycles may control these concerted or fully conjugate aza-Michael additions. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  简历 摘要 研究了活性烯烃与一级和二级胺的无催化剂反应，生成多种单氢胺化和双氢胺化产物，后者较为罕见且具有原创性。这些反应首先取决于亲核试剂的强度。温度和试剂的立体阻碍是控制这些氮杂迈克尔反应选择性的其他关键因素。尽管某些含氮杂环胺的亲核性较差，但它们仍能与不同的活性烯烃反应，生成有价值的中间体。这些结果倾向于表明，活性烯烃与多氮芳香环之间的氢键相互作用可能控制这些协同或完全共轭的氮杂迈克尔加成反应。 补充材料： 本文的补充材料以单独文件提供： mmc1.doc
• A Novel Method for the High-Pressure-Promoted, Uncatalyzed Aza-Michael Reaction of Nitrogen Heterocycles with Enones in Water
  作者：Hiyoshizo Kotsuki、Md. Uddin、Keiji Nakano、Yoshiyasu Ichikawa

  DOI：10.1055/s-2008-1072594

  日期：2008.5

  A new green chemical method for the aza-Michael reaction of nitrogen heterocycles with enones in water as a solvent without the use of any catalysts under high-pressure conditions is described.

  描述了一种新的绿色化学方法，用于在高压条件下不使用任何催化剂的水作为溶剂中氮杂环与烯酮的氮杂-迈克尔反应。
• E-factor minimized protocols for the polystyryl-BEMP catalyzed conjugate additions of various nucleophiles to α,β-unsaturated carbonyl compounds
  作者：Simona Bonollo、Daniela Lanari、Julie M. Longo、Luigi Vaccaro

  DOI：10.1039/c1gc16088e

  日期：——

  Efficient protocols for the addition of carbon-, sulphur- and nitrogen-nucleophiles to α,β-unsaturated carbonyl compounds catalyzed by PS-BEMP have been reported. The adoption of solvent-free conditions (SolFC) was crucial for improving the efficiency of all the processes, while by using an organic reaction medium poor results were obtained. Addition reactions were performed by using equimolar amounts

  添加碳，硫和硫的有效方案 氮-亲核体为α，β-不饱和 羰基化合物已经报道了由PS-BEMP催化。通过溶剂无溶剂条件（SolFC）对于提高所有过程的效率至关重要，而通过使用有机反应介质，则可获得较差的结果。使用等摩尔量的试剂进行加成反应，并通过简单的方法分离出产物过滤 用最少的有机物 溶剂。这种方法可以最大程度地减少E因子（反应浪费的量度）。通过定义在SolFC下运行的更大规模的连续流协议，可以实现进一步的废物最小化（与批处理协议相比为95.7％）。