7-Phenyl-3,4,4a,5-tetrahydro-cyclopenta[c]pyran-1,6-dione | 143121-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 7-Phenyl-3,4,4a,5-tetrahydro-cyclopenta[c]pyran-1,6-dione
• 英文别名: Cyclopenta[c]pyran-1,6-dione, 3,4,4a,5-tetrahydro-7-phenyl-；7-phenyl-3,4,4a,5-tetrahydrocyclopenta[c]pyran-1,6-dione
• CAS: 143121-34-0
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: FYZSIIUNGDKBID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  but-3-en-1-yl 3-phenylpropiolate 在 dicobalt octacarbonyl 、 N-甲基吗啉氧化物 作用下， 生成 7-Phenyl-3,4,4a,5-tetrahydro-cyclopenta[c]pyran-1,6-dione
  参考文献：
  名称：

  Pauson-Khand reaction with electron-deficient alkynes

  摘要：

  Cobalt carbonyl complexes of electron-deficient internal alkynes undergo Pauson-Khand cycloaddition efficiently and regioselectively.

  DOI：

  10.1021/jo00046a001

文献信息

• Pauson–Khand reactions in water
  作者：Marie E Krafft、James A Wright、Llorente VR Boñaga

  DOI：10.1139/v05-112

  日期：2005.6.1

  We have investigated the cobalt mediated Pauson–Khand (PK) reaction in water. In the presence of detergents and surfactants, Co₂(CO)₈ and Co₄(CO)₁₂ are effective under aqueous-phase, thermal PK reactions. In a water–Triton^®X-100 medium, Co₄(CO)₁₂ is catalytically active. Further, dicobalthexacarbonyl complexes of alkynes and enynes undergo effective cyclization under thermal (70 °C) and NMO-promoted conditions. The oxidative nature of the latter conditions inhibits the reductive PK reaction. In all protocols, moderate to excellent yields of the cycloadducts are obtained. Substrates that are prone to hydrolysis, such as acetals, highly activated carboxylic acid derivatives, and those bearing propargylic heteroatom groups are tolerated under appropriate conditions. Finally, the more challenging intermolecular cycloadditions can also be easily achieved under aqueous conditions.Key words: alkyne, cycloaddition, green chemistry, Pauson–Khand reaction, water.

  我们已经在水中研究了钴介导的Pauson-Khand（PK）反应。在存在洗涤剂和表面活性剂的情况下，Co₂(CO)₈和Co₄(CO)₁₂在水相、热力PK反应中是有效的。在水-Triton® X-100介质中，Co₄(CO)₁₂具有催化活性。此外，炔烃和烯炔烃的二钴六羰基络合物在热（70°C）和NMO促进条件下进行有效的环化反应。后一条件的氧化性质抑制了还原性PK反应。在所有方案中，环加成产物的产率从中等到优良。易水解的底物，如缩醛、高度活化的羧酸衍生物以及带有丙炔基杂原子基团的底物在适当条件下是可容忍的。最后，更具挑战性的分子间环加成也可以在水相条件下轻松实现。关键词：炔烃，环加成，绿色化学，Pauson-Khand反应，水。
• Catalytic activity of dodecacarbonyltetracobalt in aqueous media: a “greening” of the Pauson–Khand reaction
  作者：Llorente V. R. Boñaga、James A. Wright、Marie E. Krafft

  DOI：10.1039/b403827d

  日期：——

  The unprecedented reactivity of Co(4)(CO)(12) with enynes under aqueous conditions, representing the development of a mild and simple aqueous-phase cobalt-catalyzed PK reaction protocol, is described herein.

  本文描述了Co（4）（CO）（12）与烯类在水相条件下的空前反应性，代表了温和简单的水相钴催化的PK反应规程的发展。
• Pauson-Khand reaction with electron-deficient alkynes
  作者：Marie E. Krafft、Romulo H. Romero、Ian L. Scott

  DOI：10.1021/jo00046a001

  日期：1992.9

  Cobalt carbonyl complexes of electron-deficient internal alkynes undergo Pauson-Khand cycloaddition efficiently and regioselectively.