2-((4-cyanophenyl)ethynyl)cyclohex-2-enone | 1283730-75-5

• 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: 2-((4-cyanophenyl)ethynyl)cyclohex-2-enone
• 英文别名: 4-[2-(6-Oxocyclohexen-1-yl)ethynyl]benzonitrile；4-[2-(6-oxocyclohexen-1-yl)ethynyl]benzonitrile
• CAS: 1283730-75-5
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: BUWDAOCIRVWTGH-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  417.8±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((4-cyanophenyl)ethynyl)cyclohex-2-enone 在 1,1'-双(二苯基膦)二茂铁 、 碘 、 palladium diacetate 、 碳酸氢钠 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 20.0~80.0 ℃ 、101.33 kPa 条件下， 反应 9.5h， 生成 4-(5-oxo-2,3,8,9,10,10a-hexahydro-5H-[1,4]dioxocino[7,6,5-cd]benzofuran-6-yl)benzonitrile
  参考文献：
  名称：

  Highly Substituted Lactone/Ester-Containing Furan Library by the Palladium-Catalyzed Carbonylation of Hydroxyl-Substituted 3-Iodofurans

  摘要：

  Highly substituted lactone- and ester-containing furans have been prepared by the efficient palladium-catalyzed intramolecular cyclocarbonylation or intermolecular carboalkoxylation, respectively, of hydroxyl-containing 3-iodofurans, readily prepared by the iodocyclization of 2(1-alkynyl)-2-alken-1-ones in the presence of various diols.

  DOI：

  10.1021/co100088q
• 作为产物：
  描述：

  1-(4-喹啉基)甲胺 、 4-乙炔基苯甲腈 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到2-((4-cyanophenyl)ethynyl)cyclohex-2-enone
  参考文献：
  名称：

  Highly Substituted Lactone/Ester-Containing Furan Library by the Palladium-Catalyzed Carbonylation of Hydroxyl-Substituted 3-Iodofurans

  摘要：

  Highly substituted lactone- and ester-containing furans have been prepared by the efficient palladium-catalyzed intramolecular cyclocarbonylation or intermolecular carboalkoxylation, respectively, of hydroxyl-containing 3-iodofurans, readily prepared by the iodocyclization of 2(1-alkynyl)-2-alken-1-ones in the presence of various diols.

  DOI：

  10.1021/co100088q

文献信息

• Mechanism of a No-Metal-Added Heterocycloisomerization of Alkynylcyclopropylhydrazones: Synthesis of Cycloheptane-Fused Aminopyrroles Facilitated by Copper Salts at Trace Loadings
  作者：Sidney M. Wilkerson-Hill、Diana Yu、Phillip P. Painter、Ethan L. Fisher、Dean J. Tantillo、Richmond Sarpong、Jason E. Hein

  DOI：10.1021/jacs.7b06007

  日期：2017.8.2

  heterocycloisomerization reaction that forms annulated aminopyrroles is presented. Density functional theory calculations and kinetic studies suggest the reaction is catalyzed by trace copper salts and that a Z- to E-hydrazone isomerization occurs through an enehydrazine intermediate before the rate-determining cyclization of the hydrazone onto the alkyne group. The aminopyrrole products are obtained in 36-93% isolated

  介绍了形成环氨基吡咯的新杂环异构化反应的机理研究。密度泛函理论计算和动力学研究表明，该反应是由痕量铜盐催化的，并且在腙到炔基上的限速环化之前，通过烯肼中间体发生 Z 到 E 腙异构化。取决于炔基取代基的性质，以36-93%的分离产率获得氨基吡咯产物。开发了一种新的自动采样技术以获得可靠的机械数据。
• Silver(I)-Mediated Cascade Reaction of 2-(1-Alkynyl)-2-alken-1-ones with 2-Naphthols
  作者：Zhanhuan Li、Jingyi Peng、Chonglong He、Jianfeng Xu、Hongjun Ren

  DOI：10.1021/acs.orglett.0c01803

  日期：2020.8.7

  efficient cascade reaction of 2-(1-alkynyl)-2-alken-1-ones with 2-naphthols promoted by silver trifluoroacetate is disclosed, providing an expeditious access to 1,2-dihydronaphtho[2,1-b]furans with moderate to good yields. This domino process involves highly regio- and diastereoselective sequential cyclization/nucleophilic addition/oxidative ring opening/oxa-Michael addition reactions to construct three

  公开了由三氟乙酸银促进的2-（1-炔基）-2-链烯-1-酮与2-萘的有效级联反应，提供了快速接触1,2-二氢萘并[2,1- b ]呋喃的途径。中等至良好的产量。该多米诺过程涉及高度区域和非对映选择性的连续环化/亲核加成/氧化性开环/ oxa-Michael加成反应，以构建三个新的化学键和一个新的五元环。还提出了克级实验和开发不对称变体的初步结果，以显示当前反应的实用性和潜力。
• Cooperative Gold(I)/DMAP Catalysis Enabled (2 + 3) Cycloadditions of Yne–Enones with Oxindole-Derived MBH Carbonates
  作者：Hongli Zhao、Laiping Yao、Yiqiao Gu、Yadi Niu、Bo Han、Wei Huang、Gu Zhan

  DOI：10.1021/acs.orglett.4c00916

  日期：2024.5.10

  cooperative gold(I)/DMAP system catalyzes the (2 + 3) cycloadditions of yne–enones with oxindole-derived Morita–Baylis–Hillman (MBH) carbonates, yielding diverse bispiro-cyclopentene oxindole products. The mild, scalable protocol demonstrates broad substrate scope and excellent chemo- and diastereoselectivity. Mechanistic study reveals pivotal roles of both catalysts in the unique (2 + 3) cycloaddition. This

  合作的金 (I)/DMAP 系统催化炔-烯酮与羟吲哚衍生的 Morita-Baylis-Hillman (MBH) 碳酸盐发生 (2 + 3) 环加成，产生多种双螺环戊烯羟吲哚产物。温和、可扩展的方案展示了广泛的底物范围和出色的化学和非对映选择性。机理研究揭示了两种催化剂在独特的 (2 + 3) 环加成反应中的关键作用。该策略展示了通过独特的化学选择性和优异的非对映选择性实现转化的优越性，这是通过传统的单催化方法无法实现的。
• Solution-Phase Synthesis of a Highly Substituted Furan Library
  作者：Chul-Hee Cho、Feng Shi、Dai-Il Jung、Benjamin Neuenswander、Gerald H. Lushington、Richard C. Larock

  DOI：10.1021/co300040q

  日期：2012.7.9

  A library of furans has been synthesized by iodocyclization and further diversified by palladium-catalyzed coupling processes. The key intermediate 3-iodofurans have been prepared by the electrophilic iodocyclization of 2-iodo-2-alken-1-ones in the presence of various nucleophiles in good to excellent yields under mild reaction conditions. These 3-iodofurans are the key components for library generation through subsequent elaboration by palladium-catalyzed processes, such as Suzuki-Miyaura, Sonagashira, Heck, aminocarbonylation, and carboalkoxylation chemistry to afford a diverse set of 2,3,4,5-tetrasubstituted furans.
• Access to Chiral Polycyclic 1,4-Dihydropyridines via Organocatalytic Formal [3 + 3] Annulation of 2-(1-Alkynyl)-2-alken-1-ones with 3-Aminobenzofurans
  作者：Zhanhuan Li、Hongwei Zhou、Jianfeng Xu

  DOI：10.1021/acs.orglett.1c02211

  日期：2021.8.20