3-methyl-2,4-diphenylcyclopent-2-enone | 1332458-52-2

• 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: 3-methyl-2,4-diphenylcyclopent-2-enone
• 英文别名: 3-Methyl-2,4-diphenylcyclopent-2-en-1-one
• CAS: 1332458-52-2
• 化学式: C₁₈H₁₆O
• 分子量: 248.324
• InChiKey: HKBOHFCWCSJLCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-苯基-1-丙炔 、 (E)-肉桂酸苯酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 锌 、 三环己基膦 作用下， 以 异丙醇 为溶剂， 反应 5.0h， 以64%的产率得到3-methyl-2,4-diphenylcyclopent-2-enone
  参考文献：
  名称：

  Nickel-Catalyzed Formation of Cyclopentenone Derivatives via the Unique Cycloaddition of α,β-Unsaturated Phenyl Esters with Alkynes

  摘要：

  Oxygen-containing organic compounds, such as ethers, carboxylates, and carbamates, have recently received increasing attention because of their newly discovered applications as electrophiles in cross-coupling reactions via transition metal-catalyzed C-O bond activation. However, no cycloaddition reaction involving their C-O bond activation has been demonstrated thus far. The present study developed a Ni(O)-catalyzed unique [3+2] cycloaddition reaction of alpha,beta-unsaturated phenyl esters with alkynes in (PrOH)-Pr-i to yield cydopentenone derivatives.

  DOI：

  10.1021/ja2059999

文献信息

• Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition
  作者：Aireal D. Jenkins、Ananda Herath、Minsoo Song、John Montgomery

  DOI：10.1021/ja206722t

  日期：2011.9.14

  Strategies for the reductive cycloaddition of enals or enoates with alkynes have been developed. The enal-alkyne cycloaddition directly affords cyclopentenols, whereas the enoate-alkyne cycloaddition affords the analogous cyclopentenones. The mechanism of these processes likely involves formation and protonation of a metallacyclic intermediate. The general strategy provides a straightforward entry

  已经开发了烯醛或烯酸酯与炔烃的还原环加成的策略。烯醛-炔环加成直接提供环戊烯醇，而烯酸酯-炔环加成提供类似的环戊烯酮。这些过程的机制可能涉及金属环中间体的形成和质子化。一般策略提供了从简单、稳定的 π 系统到五元环产品的直接入口。
• Nickel(0)-Catalyzed Enantioselective Annulations of Alkynes and Arylenoates Enabled by a Chiral NHC Ligand: Efficient Access to Cyclopentenones
  作者：Joachim S. E. Ahlin、Pavel A. Donets、Nicolai Cramer

  DOI：10.1002/anie.201408364

  日期：2014.11.24

  nickel‐catalyzed reductive [3+2] cycloaddition of α,β‐unsaturated aromatic esters and alkynes constitutes an efficient method for their synthesis. Here, nickel(0) catalysts comprising a chiral bulky C1‐symmetric N‐heterocyclic carbene ligand were shown to enable an efficient asymmetric synthesis of cyclopentenones from mesityl enoates and internal alkynes under mild conditions. The bulky NHC ligand

  环戊烯酮是天然产物以及反应性合成中间体的多功能结构基序。镍催化的α，β-不饱和芳族酯和炔烃的还原[3 + 2]环加成反应是合成它们的有效方法。在这里，包含手性庞大的C 1-对称的N-杂环卡宾配体的镍（0）催化剂被证明能够在温和的条件下由均三烯酸酯和内部炔烃有效地不对称合成环戊烯酮。庞大的NHC配体以非常高的对映选择性提供了环戊烯酮产物，并导致不对称取代的炔烃的区域选择性结合。