1-Cyclodecyn-5-one | 78485-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Cyclodecyn-5-one
• 英文别名: 4-cyclodecynone；5-cyclodecynone；Cyclodec-4-yn-1-one
• CAS: 78485-95-7
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: VIQAZASFTMQRJD-UHFFFAOYSA-N

物化性质

• 沸点：
  256.3±29.0 °C(Predicted)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-Cyclodecyn-5-one 在 ammonium cerium(IV) nitrate 、 air 、 硝酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 60.5h， 生成 1,2,3,4-tetrahydrobenzanthracene-7,12-dione
  参考文献：
  名称：

  Studies in the benzannulation of a cycloalkynone: an approach to the synthesis of antibiotics containing the benz[a]anthracene core structure

  摘要：

  The chromium(0)-carbene complex benzannulation reaction was shown to be applicable to cyclodec-4-yn-1-one. Significant regioselectivity was realized in this reaction with ortho-substituted benzylchromium complexes. Reactions of a novel resultant fused cyclodecenone-naphthoquinone with several bases have been studied. Products apparently arising from either intramolecular Michael addition of a ketone enolate to the quinone or intramolecular aldol condensation of a quinone-stabilized anion with the ketone have been observed. The latter mode constitutes a route to the title substructure and, in principle, provides a route to reach certain angucycline antibiotics.

  DOI：

  10.1021/jo00052a014
• 作为产物：
  描述：

  1,7-Epoxy-8-oxobicyclo<5.3.0>decane 在 2,4,6-三甲基苯磺酰肼 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.33h， 生成 1-Cyclodecyn-5-one
  参考文献：
  名称：

  Use of Mesitylene-2-sulphonyl Hydrazide in the Synthesis of Medium-Ring Cycloalkynones by the Eschenmoser Fragmentation Reaction

  摘要：

  DOI：

  10.1055/s-1981-29412

文献信息

• Transannular Cyclizations of Medium-Sized Cycloalkynes and Cycloalkynones Induced by Electro- and Photochemically Generated NO3 Radicals
  作者：Uta Wille、Christian Plath

  DOI：10.1002/jlac.199719970117

  日期：1997.1

  Transannular radical cyclizations of medium-sized cycloalkynes and cycloalkynones induced by addition of NO3 radicals to the C–C triple bond were studied. In the reaction of NO3 with medium-sized cycloalkynes oxidation of the triple bond to a carbonyl group occurred and formation of cis-fused bicyclic alkanones by transannular cyclization was observed. In the reaction of NO3 radicals with medium-sized

  研究了中型环炔烃和环炔酮的环戊基环化反应，该环化反应是通过将NO 3自由基加至C-C三键而引起的。在NO 3与中型环炔烃的反应中，发生了三键氧化成羰基的现象，并观察到通过环过环化形成顺式稠合双环烷酮。在NO 3自由基与中等大小的环炔酮的反应中，α，β-环氧酮以环空反应顺序形成，可以正式地认为是Eschenmoser-Ohloff逆向裂解反应。介绍了这些反应的范围和局限性，并提出了反应机理。
• Mechanism of the transannular cyclization of 5-cyclodecynone
  作者：Charles E. Harding、G. Richard Stanford

  DOI：10.1021/jo00274a018

  日期：1989.6
• REESE C. B.; SANDERS H. P., SYNTHESIS, 1981, NO 4, 276-278
  作者：REESE C. B.、 SANDERS H. P.

  DOI：——

  日期：——
• Use of Mesitylene-2-sulphonyl Hydrazide in the Synthesis of Medium-Ring Cycloalkynones by the Eschenmoser Fragmentation Reaction
  作者：Colin B. Reese、H. Paul Sanders

  DOI：10.1055/s-1981-29412

  日期：——
• Studies in the benzannulation of a cycloalkynone: an approach to the synthesis of antibiotics containing the benz[a]anthracene core structure
  作者：Dana M. Gordon、Samuel J. Danishefsky、Gayle K. Schulte

  DOI：10.1021/jo00052a014

  日期：1992.12

  The chromium(0)-carbene complex benzannulation reaction was shown to be applicable to cyclodec-4-yn-1-one. Significant regioselectivity was realized in this reaction with ortho-substituted benzylchromium complexes. Reactions of a novel resultant fused cyclodecenone-naphthoquinone with several bases have been studied. Products apparently arising from either intramolecular Michael addition of a ketone enolate to the quinone or intramolecular aldol condensation of a quinone-stabilized anion with the ketone have been observed. The latter mode constitutes a route to the title substructure and, in principle, provides a route to reach certain angucycline antibiotics.