4-(but-2-ynyloxy)-3,4-dimethylcyclohexa-2,5-dienone | 1184937-24-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(but-2-ynyloxy)-3,4-dimethylcyclohexa-2,5-dienone
• 英文别名: 4-But-2-ynoxy-3,4-dimethylcyclohexa-2,5-dien-1-one
• CAS: 1184937-24-3
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: SFPCQZYXRKKZRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(but-2-ynyloxy)-3,4-dimethylcyclohexa-2,5-dienone 、 溶剂黄146 在 2,2'-联吡啶 、 palladium diacetate 作用下， 生成 C₁₄H₁₈O₄
  参考文献：
  名称：

  Bicyclic Cyclohexenones as Inhibitors of NF-κB Signaling

  摘要：

  A series of structurally simplified cryptocaryone analogues were synthesized by a facile Pd-catalyzed acetoxylation of alkyne-tethered cyclohexadienones and evaluated as inhibitors of NF-kappa B signaling. Compounds 10 and 11 were found to possess low micromolar inhibitory properties toward induced NF-kappa B activity by blocking p50/p65 nuclear protein through a covalent inhibition mechanism. Both compounds were: able to inhibit NF-kappa B-induced IL-8 expression and exhibited antiproliferative activity against two model cancer cell lines. These analogues constitute a promising new scaffolc. for the development of novel NF-kappa B inhibitors and anticancer agents.

  DOI：

  10.1021/ml300034a
• 作为产物：
  描述：

  3,4-二甲基苯酚 、 2-丁炔-1-醇 在 碘苯二乙酸 作用下， 反应 0.5h， 以42%的产率得到4-(but-2-ynyloxy)-3,4-dimethylcyclohexa-2,5-dienone
  参考文献：
  名称：

  Palladium-Catalyzed Reactions of Cyclohexadienones: Regioselective Cyclizations Triggered by Alkyne Acetoxylation

  摘要：

  Regioselective cyclizations of alkyne-tethered cyclohexadienones can be accomplished under palladium catalysis. The cyclization involves an Initial Pd-mediated acetoxylation of the alkyne, followed by migratory insertion and protonolysis of the resulting palladium enolate. The predictable regloselectivity of these atom-economical and stereoselective reactions is influenced by developing steric interactions during migratory insertion of a vinyl palladium intermediate.

  DOI：

  10.1021/ol901642w

文献信息

• Palladium-catalyzed desymmetric [2+2+2] cycloaddition of 1,6-enyne and alkyne
  作者：Wei-Cheng Zhao、Xin Wang、Juhua Feng、Ping Tian、Zhi-Tao He

  DOI：10.1016/j.tet.2020.131862

  日期：2021.1

  desymmetric [2+2+2] cycloaddition reaction of alkyne-tethered cyclohexadienone and internal alkyne is established. Widely existing fused tricyclic hydronaphthofuran and hydronaphthopyrrole frameworks are prepared diastereoselectively in moderate to excellent yields. One-step aromatization process provides a new and facile access to important benzene-containing tricycles from above cycloaddition products

  建立了新颖且直接的炔烃系环己二酮与内部炔烃的钯催化不对称[2 + 2 + 2]环加成反应。非对映选择性地以中等到优异的产率制备了广泛存在的稠合三环氢萘呋喃和氢萘吡咯骨架。一步芳构化工艺提供了一种新的途径，可以轻松地从上述环加成产物中获得重要的含苯三环。