bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-1-ium chloride | 1192453-20-5

• 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: bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-1-ium chloride
• CAS: 1192453-20-5
• 化学式: C₂₈H₄₁N₂*Cl
• 分子量: 441.1
• InChiKey: WGOHEEJAILXOFV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  31.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  6.25
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-1-ium chloride 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (6-Dipp)CuO^tBu
  参考文献：
  名称：

  新型氢化铜（I）二聚体的合成与反应性

  摘要：

  The expanded-ring N-heterocyclic carbenes 6Dipp and 7Dipp (6Dipp = 1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene and 7Dipp = 1,3-bis(2,6-diisopropylphenyl)-4,5,6,7-tetrahydro-1,3-diazepin-2-ylidene) support isolable neutral copper hydride dimers. [(6Dipp)CuH](2) reacts with 1-hexene to give (6Dipp)copper(I) hexyl by 1,2-insertion and with benzyl isonitrile to afford an C-1-formimidoyl by 1,1-insertio

  DOI：

  10.1021/acs.organomet.6b00025
• 作为产物：
  描述：

  (1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-1-ium)BF4 在 Amberlite IRA₄₀₂ chloride resin 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-1-ium chloride
  参考文献：
  名称：

  环膨胀N-杂环碳（RE-NHC）铜配合物的合成途径及其在Click化学中的性能

  摘要：

  据报道环扩展的N-杂环卡宾（RE-NHC）卤化铜（I）配合物的简便合成。该方法利用绿色溶剂中的弱无机碱。通过在微波辐射下使用这种弱碱路线，可以大大缩短反应时间。容易获得这些络合物可以评估Huisgen 1,3-环加成反应中[Cu（RE-NHC）X]络合物的催化活性和反应谱。

  DOI：

  10.1021/acs.organomet.1c00039
• 作为试剂：
  描述：

  反式肉桂醛 、 对硝基苯酚 在 bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-1-ium chloride 、 palladium diacetate 、 sodium carbonate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 48.0h， 以25%的产率得到trans-Zimtsaeure-p-nitrophenylester
  参考文献：
  名称：

  Palladium/NHC-catalyzed oxidative esterification of aldehydes with phenols

  摘要：

  A palladium-catalyzed oxidative esterification of aldehydes with phenols is described, using air as the clean oxidant. This reaction tolerates many functional groups, providing esters with yields ranging from moderate to excellent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.017

文献信息

• Synthesis of Isocoumarins through Three-Component Couplings of Arynes, Terminal Alkynes, and Carbon Dioxide Catalyzed by an NHC-Copper Complex
  作者：Woo-Jin Yoo、Thanh V. Q. Nguyen、Shū Kobayashi

  DOI：10.1002/anie.201404692

  日期：2014.9.15

  A copper‐catalyzed multicomponent coupling reaction between in situ generated ortho‐arynes, terminal alkynes, and carbon dioxide was developed to access isocoumarins in moderate to good yields. The key to this CO2‐incorporating reaction was the use of a versatile N‐heterocyclic carbene/copper complex that was able to catalyze multiple transformations within the three‐component reaction.

  开发了铜催化的原位生成的原芳烃，末端炔烃和二氧化碳之间的多组分偶联反应，以中等到良好的产率获得了异香豆素。引入CO 2的反应的关键是使用通用的N杂环卡宾/铜配合物，该配合物能够催化三组分反应中的多种转化。
• Structure and Bonding in Neutral and Cationic 14‐Electron Gold Alkyne π Complexes
  作者：Susanne Flügge、Anakuthil Anoop、Richard Goddard、Walter Thiel、Alois Fürstner

  DOI：10.1002/chem.200901062

  日期：2009.8.24

  Cyclododecyne (5) as a prototype unstrained alkyne was coordinated to either the neutral [AuCl] fragment or to two different cationic [Au(NHC)]+ entities (NHC=N‐heterocyclic carbene), and the resulting complexes 6, 8, and 10 were characterized by X‐ray crystallography and NMR spectroscopy. Since the structure of cyclododecyne in the solid state could also be obtained after in situ crystallization,

  环十二炔( 5 ) 作为原型无应变炔烃与中性 [AuCl] 片段或两种不同的阳离子 [Au(NHC)] +实体 (NHC=N-杂环卡宾) 配位，得到配合物6、8和10用 X 射线晶体学和核磁共振光谱对其进行了表征。由于固态环十二炔的结构也可以在原位结晶后获得，因此可以进行比较，以深入了解不同金碎片对炔烃施加的结构变化。这些数据是基于对单个化合物中键合情况的 DFT 分析进行解释的，这为许多金催化转化常见的第一个基本步骤提供了见解。
• Dial-a-base mechanochemical synthesis of N-heterocyclic carbene copper complexes
  作者：Dawid J. Babula、Rex S. C. Charman、Josie A. Hobson、Mary F. Mahon、David J. Liptrot

  DOI：10.1039/d4dt00334a

  日期：——

  Liquid assisted ball milling of [NHC]HBr (NHC = N-heterocyclic carbene) salts with copper(I) chloride, and a range of alkali metal complexes was shown to efficiently produce (NHC)CuX (NHC = normal or RE-NHC, X = halide, alkoxide, amide, alkyl, aryl; RE-NHC = ring-expanded NHC).

  [NHC]HBr (NHC = N-杂环卡宾) 盐与氯化铜 ( I ) 和一系列碱金属络合物的液体辅助球磨可有效生产 (NHC)CuX（NHC = 正常或 RE-NHC， X = 卤化物、醇盐、酰胺、烷基、芳基；RE-NHC = 扩环 NHC)。
• Synthetic Access to Ring-Expanded N-Heterocyclic Carbene (RE-NHC) Copper Complexes and Their Performance in Click Chemistry
  作者：Jonathan W. Hall、Damien Bouchet、Mary F. Mahon、Michael K. Whittlesey、Catherine S. J. Cazin

  DOI：10.1021/acs.organomet.1c00039

  日期：2021.5.10

  syntheses of ring-expanded N-heterocyclic carbene (RE-NHC) copper(I) halide complexes are reported. The method makes use of a weak inorganic base in a green solvent. The reaction times can be greatly reduced by use of this weak-base route under microwave irradiation. The easy access to these complexes permits an evaluation of the catalytic activity and reaction profiling of [Cu(RE-NHC)X] complexes in

  据报道环扩展的N-杂环卡宾（RE-NHC）卤化铜（I）配合物的简便合成。该方法利用绿色溶剂中的弱无机碱。通过在微波辐射下使用这种弱碱路线，可以大大缩短反应时间。容易获得这些络合物可以评估Huisgen 1,3-环加成反应中[Cu（RE-NHC）X]络合物的催化活性和反应谱。
• Synthesis and Reactivity of New Copper(I) Hydride Dimers
  作者：Abraham J. Jordan、Chelsea M. Wyss、John Bacsa、Joseph P. Sadighi

  DOI：10.1021/acs.organomet.6b00025

  日期：2016.3.14

  The expanded-ring N-heterocyclic carbenes 6Dipp and 7Dipp (6Dipp = 1,3-bis(2,6-diisopropylphenyl)-3,4,5,6-tetrahydropyrimidin-2-ylidene and 7Dipp = 1,3-bis(2,6-diisopropylphenyl)-4,5,6,7-tetrahydro-1,3-diazepin-2-ylidene) support isolable neutral copper hydride dimers. [(6Dipp)CuH](2) reacts with 1-hexene to give (6Dipp)copper(I) hexyl by 1,2-insertion and with benzyl isonitrile to afford an C-1-formimidoyl by 1,1-insertio