(E)-4-benzylidene-3-methyl-2-phenylcyclopent-2-en-1-one | 96095-49-7

• 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: (E)-4-benzylidene-3-methyl-2-phenylcyclopent-2-en-1-one
• 英文别名: (4E)-4-benzylidene-3-methyl-2-phenylcyclopent-2-en-1-one
• CAS: 96095-49-7
• 化学式: C₁₉H₁₆O
• 分子量: 260.335
• InChiKey: JRDGQCUFNFPTIQ-SFQUDFHCSA-N

物化性质

• 沸点：
  459.9±45.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-Methyl-5-(phenylmethyl)furan 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 (E)-4-benzylidene-3-methyl-2-phenylcyclopent-2-en-1-one
  参考文献：
  名称：

  Stereoselective Synthesis of (E)-4-Alkylidenecyclopent-2-en-1-ones by a Tandem Ring Closure−Michael Addition−Elimination

  摘要：

  [GRAPHICS]Reaction of (Z)-1,4-diketones with various functionalized nitroalkanes in the presence of DBU gives 4-alkylidenecyclopent-2-en-1-ones with E selectivity, A cyclopentadienone intermediate is probably formed by intramolecular aldol condensation, and this reacts with a nitroalkane giving a Michael addition-elimination.

  DOI：

  10.1021/ol0069352

文献信息

• Rhodium-Catalyzed Intermolecular Carbonylative [2 + 2 + 1] Cycloaddition of Alkynes Using Alcohol as the Carbon Monoxide Source for the Formation of Cyclopentenones
  作者：Ju Hyun Kim、Taemoon Song、Young Keun Chung

  DOI：10.1021/acs.orglett.7b00458

  日期：2017.3.3

  regioselective rhodium-catalyzed intermolecular carbonylative [2 + 2 + 1] cycloaddition of alkynes using alcohol as a CO surrogate to access 4-methylene-2-cyclopenten-1-ones has been developed. In this transformation, the alcohol performs multiple roles, including generating the Rh–H intermediate, functioning as the CO source, and assisting in the isomerization of the alkyne. Alkynes can act as both the olefin

  已开发出一种高度区域选择性的铑催化的炔烃分子间羰基化[2 + 2 + 1]环加成反应，使用醇作为一氧化碳替代物，以生成4-亚甲基-2-环戊烯-1-酮。在这种转化中，醇具有多种作用，包括生成Rh–H中间体，充当CO源以及协助炔烃的异构化。炔烃可以同时充当环戊烯酮核心中的烯烃和炔烃伙伴。
• Study of the reactions of substituted allenes with tris(triphenylphosphine)nickel(0). An analysis of the factors affecting the regio- and stereochemistry of .pi.-complex formation and coupling to form nickelacyclopentane complexes
  作者：Daniel J. Pasto、Naizhong Huang、Charles W. Eigenbrot

  DOI：10.1021/ja00297a022

  日期：1985.5
• Aumann, Rudolf; Uphoff, Juergen, Angewandte Chemie, 1987, vol. 99, # 4, p. 361 - 362
  作者：Aumann, Rudolf、Uphoff, Juergen

  DOI：——

  日期：——
• Stereoselective Synthesis of (<i>E</i>)-4-Alkylidenecyclopent-2-en-1-ones by a Tandem Ring Closure−Michael Addition−Elimination
  作者：Roberto Ballini、Giovanna Bosica、Dennis Fiorini、Maria Victoria Gil、Marino Petrini

  DOI：10.1021/ol0069352

  日期：2001.5.1

  [GRAPHICS]Reaction of (Z)-1,4-diketones with various functionalized nitroalkanes in the presence of DBU gives 4-alkylidenecyclopent-2-en-1-ones with E selectivity, A cyclopentadienone intermediate is probably formed by intramolecular aldol condensation, and this reacts with a nitroalkane giving a Michael addition-elimination.