phenyl(2-phenylcyclopent-2-en-1-yl)methanone | 1601-09-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl(2-phenylcyclopent-2-en-1-yl)methanone
• 英文别名: 1-phenyl-5-benzoylcyclopentene；phenyl-(2-phenyl-cyclopent-2-enyl)-ketone；Phenyl-(2-phenyl-cyclopent-2-enyl)-keton；1-Phenyl-2-benzoyl-cyclopenten-(5)；(+/-)-Phenyl-<2-phenyl-cyclopent-2-enyl>-keton；2-Benzoyl-1-phenyl-cyclopent-5-en；Ketone, phenyl 2-phenyl-2-cyclopenten-1-yl；phenyl-(2-phenylcyclopent-2-en-1-yl)methanone
• CAS: 1601-09-8
• 化学式: C₁₈H₁₆O
• 分子量: 248.324
• InChiKey: MLJGTOVDVQNNRY-UHFFFAOYSA-N

物化性质

• 熔点：
  98 °C
• 沸点：
  392.4±42.0 °C(Predicted)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  phenyl(2-phenylcyclopent-2-en-1-yl)methanone 在 sodium amide 、 苯 作用下， 生成 1-phenyl-5-methylcyclopentene
  参考文献：
  名称：

  Bauer, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1913, vol. 156, p. 1472

  摘要：

  DOI：
• 作为产物：
  描述：

  己二酰氯 在 aluminum (III) chloride 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 26.08h， 生成 phenyl(2-phenylcyclopent-2-en-1-yl)methanone
  参考文献：
  名称：

  AlCl₃-Mediated Aldol Cyclocondensation of 1,6- and 1,7-Diones to Cyclopentene and Cyclohexene Derivatives

  摘要：

  Exactly 1/3 mol of AlCl3 is sufficient to cyclize 1 mol of 1,omega-dibenzoylbutane (or pentane) to a cyclopentenone (or hexenone) derivative in high yield at room temperature in 40 min to several hours. This condensation is driven by removing elements of water as HCl and Al(OH)(3), and the product enones are exclusively unconjugated, unlike the base-catalyzed condensations providing thermodynamically more stable conjugated enones.

  DOI：

  10.1021/jo5006137

文献信息

• Tropylium-promoted carbonyl–olefin metathesis reactions
  作者：Uyen P. N. Tran、Giulia Oss、Domenic P. Pace、Junming Ho、Thanh V. Nguyen

  DOI：10.1039/c8sc00907d

  日期：——

  carbonyl–olefin metathesis (COM) reaction is a highly valuable chemical transformation in a broad range of applications. However, its scope is much less explored compared to analogous olefin–olefin metathesis reactions. Herein we demonstrate the use of tropylium ion as a new effective organic Lewis acid catalyst for both intramolecular and intermolecular COM and new ring-opening metathesis reactions. This represents

  羰基-烯烃复分解 (COM) 反应是一种在广泛应用中非常有价值的化学转化。然而，与类似的烯烃-烯烃复分解反应相比，其范围的探索要少得多。在此，我们展示了将鎓离子用作分子内和分子间 COM 和新的开环复分解反应的新型有效有机路易斯酸催化剂。与最近报道的该领域的发展相比，这代表了底物范围的显着改进。
• Carbonyl–Olefin Metathesis Catalyzed by Molecular Iodine
  作者：Uyen P. N. Tran、Giulia Oss、Martin Breugst、Eric Detmar、Domenic P. Pace、Kevin Liyanto、Thanh V. Nguyen

  DOI：10.1021/acscatal.8b03769

  日期：2019.2.1

  The carbonyl–olefin metathesis reaction could facilitate rapid functional group interconversion and allow construction of complicated organic structures. Herein, we demonstrate that elemental iodine, a very simple catalyst, can efficiently promote this chemical transformation under mild reaction conditions. Our mechanistic studies revealed intriguing aspects of the activation mode via molecular iodine

  羰基-烯烃复分解反应可以促进官能团的快速相互转化，并可以构建复杂的有机结构。在这里，我们证明元素碘，一种非常简单的催化剂，可以在温和的反应条件下有效地促进这种化学转化。我们的机理研究揭示了通过分子碘和碘鎓离子引起的活化模式的有趣方面，这些方面可能会改变先前建立的对羰基-烯烃复分解反应的催化剂和底物设计的认识。
• AuCl ₃ ‐Catalyzed Ring‐Closing Carbonyl–Olefin Metathesis
  作者：Rui Wang、Yi Chen、Mao Shu、Wenwen Zhao、Maoling Tao、Chao Du、Xiaoya Fu、Ao Li、Zhihua Lin

  DOI：10.1002/chem.201905199

  日期：2020.2.11

  Compared with the ripeness of olefin metathesis, exploration of the construction of carbon-carbon double bonds through the catalytic carbonyl-olefin metathesis reaction remains stagnant and has received scant attention. Herein, a highly efficient AuCl3 -catalyzed intramolecular ring-closing carbonyl-olefin metathesis reaction is described. This method features easily accessible starting materials,

  与烯烃复分解的成熟相比，通过催化羰基-烯烃复分解反应构建碳-碳双键的研究仍然停滞不前，受到关注的很少。在此，描述了高效的AuCl 3催化的分子内闭环羰基-烯烃复分解反应。该方法具有易于获得的原料，操作简单，对官能团的耐受性强和反应时间短的特点，并以优异的产率提供了目标环戊烯，多环化合物，苯并碳环化合物和N-杂环衍生物。
• Iodonium-Catalyzed Carbonyl–Olefin Metathesis Reactions
  作者：Giulia Oss、Thanh Vinh Nguyen

  DOI：10.1055/s-0039-1690297

  日期：2019.10

  organic synthesis due to its versatility in functional group interconversion chemistry. Recent developments in the field have identified a number of transition-metal and organic Lewis acids as effective catalysts for this reaction. Herein, we report the use of simple organic compounds such as N-iodosuccinimide or iodine monochloride to catalyze the carbonyl–olefin metathesis process under mild reaction

  羰基-烯烃复分解反应由于其在官能团互变化学中的多功能性而在有机合成中变得越来越重要。该领域的最新发展已确定许多过渡金属和有机路易斯酸可作为该反应的有效催化剂。在此，我们报告了使用简单的有机化合物（如 N-碘代琥珀酰亚胺或一氯化碘）在温和的反应条件下催化羰基-烯烃复分解过程。这项工作扩大了这种化学转化的范围，将碘源作为简单实用的催化剂。
• Hydrogen Bonding Networks Enable Brønsted Acid‐Catalyzed Carbonyl‐Olefin Metathesis**
  作者：Tuong Anh To、Chao Pei、Rene M. Koenigs、Thanh Vinh Nguyen

  DOI：10.1002/anie.202117366

  日期：2022.3.21

  H-bonding network: Hexafluoroisopropanol (HFIP) can act as a hydrogen-bond donor to enhance the catalytic efficiency of simple Brønsted acid catalysts in carbonyl-olefin metathesis reactions by stabilization of all transition states and intermediates along the reaction pathway.

  氢键网络：六氟异丙醇（HFIP）可以作为氢键供体，通过稳定反应路径上的所有过渡态和中间体来提高简单布朗斯台德酸催化剂在羰基-烯烃复分解反应中的催化效率。