(cyclohexylbuta-1,3-diyn-1-yl)benzene | 1397699-70-5

• 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: (cyclohexylbuta-1,3-diyn-1-yl)benzene
• 英文别名: 1-(4-cyclohexylbuta-1,3-diynyl)benzene；4-Cyclohexylbuta-1,3-diynylbenzene；4-cyclohexylbuta-1,3-diynylbenzene
• CAS: 1397699-70-5
• 化学式: C₁₆H₁₆
• 分子量: 208.303
• InChiKey: HTMCNHFDDFWAQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  (cyclohexylbuta-1,3-diyn-1-yl)benzene 在 肼 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 20.0h， 以81%的产率得到5-benzyl-3-cyclohexyl-1H-pyrazole
  参考文献：
  名称：

  Synthesis of 3,5-Disubstituted Pyrazoles via Cope-Type Hydroamination of 1,3-Dialkynes

  摘要：

  An efficient method for the synthesis of 3,5-disubstituted pyrazoles is described. The reactions of 1,3-dialkynes with hydrazine proceeded smoothly in dimethyl sulfoxide under mild reaction conditions to produce 3,5-disubstituted pyrazoles in satisfactory to excellent yields. A one-pot procedure of the transformation has been developed.

  DOI：

  10.1021/jo302732v
• 作为产物：
  描述：

  苯乙炔 在 正丁基锂 、 copper(II) ferrite 、 caesium carbonate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 11.0h， 生成 (cyclohexylbuta-1,3-diyn-1-yl)benzene
  参考文献：
  名称：

  Cu-Catalyzed Fe-Driven C_sp–C_sp and C_sp–C_sp2 Cross-Coupling: An Access to 1,3-Diynes and 1,3-Enynes

  摘要：

  An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.

  DOI：

  10.1021/jo5011069

文献信息

• Mesoporous Copper/Manganese Oxide Catalyzed Coupling of Alkynes: Evidence for Synergistic Cooperative Catalysis
  作者：Sourav Biswas、Kankana Mullick、Sheng-Yu Chen、David A. Kriz、MD Shakil、Chung-Hao Kuo、Alfredo M. Angeles-Boza、Angelo R. Rossi、Steven L. Suib

  DOI：10.1021/acscatal.6b00717

  日期：2016.8.5

  Copper oxide supported on mesoporous manganese oxide (meso Cu/MnOx) was synthesized by an inverse micelle templated evaporation induced self-assembly procedure. Controlled aggregation of nanoparticles and a monomodal size distribution of mesopores with tunable structural properties were observed. The material possessed superior catalytic activity in the aerobic oxidative coupling of terminal alkynes

  介孔锰氧化物上负载的氧化铜（介孔Cu / MnO x通过逆胶束模板化的蒸发诱导自组装程序合成）。观察到纳米粒子的受控聚集和具有可调结构特性的介孔的单峰尺寸分布。该物质在末端炔烃的好氧氧化偶合中具有优异的催化活性。使用优化的反应条件，在炔烃的均相偶联和交叉偶联中均观察到优异的转化率（大多数情况下> 99％）和选择性。使用空气作为唯一的氧化剂，避免使用任何种类的添加剂，易于产品分离，具有强大的官能团耐受性，广泛的合成范围以及出色的可重复使用性（直至第八个循环）是我们催化方案的显着特征。在阐明了反应机理的同时，已经建立了铜和锰之间的协同协同作用，这是其优越的催化活性的原因。中观Cu / MnO的不稳定晶格氧在TPD和TGA研究的支持下， x在炔烃质子的去质子化中起着至关重要的作用。此外，我们首次通过DFT计算为催化剂的活性位点设计了模型配合物，并提供了对偶联机理的定性描述，从而支持了实验结果。
• Reduced graphene oxide supported copper oxide nanocomposites: An efficient heterogeneous and reusable catalyst for the synthesis of ynones, 1,3‐diynes and 1,5‐benzodiazepines in one‐pot under sustainable reaction conditions
  作者：Rajib Sarkar、Ajay Gupta、Ramen Jamatia、Amarta Kumar Pal

  DOI：10.1002/aoc.5646

  日期：2020.7

  A greener and efficient method for the synthesis of ynones and 1,3‐diynes using copper oxide nanoparticles (CuONPs) doped reduced graphene oxide (CuO@rGO) catalyst under palladium, ligand and solvent free conditions have been developed. The catalyst was subsequently utilized for the synthesis of biologically active 1,5‐benzodiazepines in one pot via sequential addition of acyl chlorides, terminal alkynes

  开发了一种绿色环保，高效的方法，该方法使用钯，配体和无溶剂条件下的氧化铜纳米颗粒（CuONPs）掺杂的还原氧化石墨烯（CuO @ rGO）催化剂合成炔酮和1,3-二炔。该催化剂随后通过依次添加酰氯，末端炔烃和邻苯二胺在一个锅中用于合成具有生物活性的1,5-苯并二氮杂s。该方法最初涉及在乙醇存在下与邻苯二胺反应的原位形成炔酮，以提供多种苯并二氮杂pine。温和的反应条件，良好的产物收率，廉价且可回收的催化剂使该方法在环境方面无害且可持续。
• One‐pot synthesis of unsymmetrical 1,3‐butadiyne derivatives
  作者：Zhicai Zhao

  DOI：10.1002/bkcs.12762

  日期：2023.10

  An efficient co-operative Ni/Cu system for Cadiot–Chodkiewicz coupling utilizes CaC2 as the alkyne source. The advantage of this cross-coupling reaction lies in the low cost of using cheap and readily available raw materials and the simplicity of operation. A series of functionalized diaryl, aryl-alkyl, and aryl-heteroaryl 1,3-diynes are obtained in moderate to high yields.

  Cadiot-Chodkiewicz 耦合的高效协同 Ni/Cu 系统利用 CaC 2作为炔烃源。这种交叉偶联反应的优点在于使用廉价易得的原材料成本低且操作简单。以中等到高产率获得了一系列官能化二芳基、芳基-烷基和芳基-杂芳基1,3-二炔。
• Multicomponent Synthesis of 3(2H)‐Furanones Initiated by Copper(II)‐Catalyzed Alkyne‐Carbonyl Cross Metathesis
  作者：Zhenjie Su、Shaozhong Wang

  DOI：10.1002/chem.202401999

  日期：2024.8.27

  The cooperative Lewis- and Brønsted acid catalysis enables a multicomponent synthesis of 3(2H)-furanones from 1,3-diynes, alkyl glyoxylates and water, in which a highly chemo-, regio- and stereoselective alkyne-carbonyl cross metathesis of 1,3-diynes has been developed and suggested as the initial step of the annulation.

  路易斯酸和布朗斯台德酸协同催化能够从 1,3-二炔、乙醛酸烷基酯和水多组分合成 3(2H)-呋喃酮，其中 1、 3-二炔已被开发并建议作为环化的初始步骤。
• Copper-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with 1,1-Dibromo-1-alkenes
  作者：Zheng Huang、Rui Shang、Zi-Rong Zhang、Xiao-Dan Tan、Xiao Xiao、Yao Fu

  DOI：10.1021/jo400616r

  日期：2013.5.3

  A copper-catalyzed decarboxylative coupling reaction of potassium alkynyl carboxylates with 1,1-dibromo-1-alkenes was developed for the synthesis of unsymmetrical 1,3-diyne and 1,3,5-triyne derivatives. Diverse aryl, alkenyl, alkynyl, and alkyl substituted 1,1-dibromo-1-alkenes can react smoothly with aryl and alkyl substituted propiolates to produce unsymmetrical 1,3-diynes and 1,3,5-triynes with high selectivity and good functional group compatibility.