4-(but-2-ynyloxy)-2,4-dimethylcyclohexa-2,5-dienone | 1184937-25-4

• 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)-2,4-dimethylcyclohexa-2,5-dienone
• 英文别名: 4-But-2-ynoxy-2,4-dimethylcyclohexa-2,5-dien-1-one
• CAS: 1184937-25-4
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: MXNSENLIPQOIKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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)-2,4-dimethylcyclohexa-2,5-dienone 、 溶剂黄146 在 2,2'-联吡啶 、 palladium diacetate 作用下， 生成 1-(6,7a-dimethyl-5-oxo-3a,4-dihydro-1-benzofuran-3-ylidene)ethyl acetate
  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：

  2-丁炔-1-醇 、 2,4-二甲基苯酚 在 碘苯二乙酸 作用下， 反应 0.5h， 以47%的产率得到4-(but-2-ynyloxy)-2,4-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