cyclopentenone | 58774-08-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cyclopentenone
• 英文别名: tetraphenylcyclopentadienone；2,3,4,5-tetraphenylcyclopentadienone；2,3,4,5-Tetraphenyl-cyclopent-3-enon；2,3,4,5-Tetraphenylcyclopentenon；2,3,4,5-Tetraphenylcyclopent-3-en-1-one
• CAS: 58774-08-6
• 化学式: C₂₉H₂₂O
• 分子量: 386.493
• InChiKey: ZIFUPAPAQKKQOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  cyclopentenone 在 CaO₂*2H₂O₂ 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到1,2,3,4-四苯基-2-丁烯-1,4-二酮
  参考文献：
  名称：

  过氧化钙二氧水合物可作为有机合成的可存储单线态氧的化学生成剂。

  摘要：

  过氧化钙二氧水合物（CaO（2）.2H（2）O（2））是可用于有机合成的单线态氧（（1）O（2），（1）Delta（g））的环保型发生器作为常规光化学方法的替代方法。该化合物在各种溶剂中产生（1）O（2），可以很容易地通过过滤回收以进一步再生。监视（1）O（2）在1270 nm处的发光以及特定的捕获都显示CaO（2）.2H（2）O（2）可以在-80摄氏度下存储几天，并且（ 1）O（2）等于25％。通过[4 + 2]或[2 + 2]环加成反应和甲醇反应，可以在甲醇或THF中对典型的有机底物进行氧化，并且制备规模达到了总转化率和选择性。

  DOI：

  10.1021/jo010766x
• 作为产物：
  描述：

  四苯基环戊二烯酮 在 甲基膦酸 、 三乙胺 作用下， 以 苯 为溶剂， 生成 cyclopentenone
  参考文献：
  名称：

  Fookes,C.J.R.; Gallagher,M.J., Journal of the Chemical Society. Perkin transactions I, 1975, p. 1876 - 1879

  摘要：

  DOI：

文献信息

• A chemical and thermochemical study of non-observed symmetry allowed reactions
  作者：S. Ranganathan、D. Ranganathan、P.V. Ramachandran、M.K. Mahanty、S. Bamezai

  DOI：10.1016/0040-4020(81)85008-9

  日期：1981.1

  A variety of reactions, whilst predicted to be symmetry allowed, are not observed experimentally. Several such non-observed yet allowed reactions have been studied in order to understand them and to possibly bring about, with suitably modified substrates, their observation. For example, although ozone adds to π-bonds, the isoelectronic nitro group does not, due to a high activation energy barrier.

  虽然预计不会出现对称反应，但无法通过实验观察到各种反应。为了理解它们并可能通过适当修饰的底物进行观察，已研究了几种此类未观察到但允许的反应。例如，尽管臭氧加成了π键，但是由于高的活化能垒，因此等电子硝基没有。该反应的类型为A→B→C。一系列1,3-偶极子物种的分子轨道计算表明，在[4 + 2]加成中π键顺序与其有效性相关。基于此，硝基和臭氧都应视为不良的偶极试剂。异常高的ΔH ˚F °臭氧的（+ 34.00千卡摩尔-1）与硝基苯（+3.8 kcal mol -1）相比，可能可以解释前者的反应性。这反映在-45.5千卡mol的估计ΔH°值-1的乙烯-臭氧加成与+ 7.5千卡摩尔比-1的非存在的乙烯-硝基苯加成。热化学计算表明，与作为1，3-偶极试剂相比，硝基更容易以2π伴侣形式加成。
• REACTIONS OF BENZENES WITH ACETYLENES CATALYZED BY RHODIUM CARBONYL UNDER CARBON MONOXIDE
  作者：Pangbu Hong、Bo-Re Cho、Hiroshi Yamazaki

  DOI：10.1246/cl.1979.339

  日期：1979.4.5

  The reaction of benzene with diphenylacetylene catalyzed by Rh4(CO)12 under carbon monoxide gives triphenylethylene and 2,3-diphenylindenone. The reactions of mono-/di-substituted benzenes with the acetylene also give the corresponding olefins and 2,3-diphenylindenones.

  苯与二苯乙炔在一氧化碳下由 Rh4(CO)12 催化反应生成三苯乙烯和 2,3-二苯茚酮。单/二取代苯与乙炔的反应也产生相应的烯烃和 2,3-二苯基茚酮。
• Controlled deposition of large-area and highly-ordered thin films: effect of dip-coating-induced morphological evolution on resistive memory performance
  作者：Yang Li、Cheng Zhang、Zhuang Li、Peiyang Gu、Zilong Wang、Hua Li、Jianmei Lu、Qichun Zhang

  DOI：10.1039/c9tc00431a

  日期：——

  efficient technique that enables both large-scale production and nano-scale control is highly desirable but very challenging for achieving high-performance organic-based memory electronic devices. Herein, we employed a dip-coating method to fabricate reliable and cost-effective organic memory devices (OMDs). This technique enables us to deposit high-quality, homogeneous and large-area nanopatterns on the

  迫切需要开发一种既能实现大规模生产又能进行纳米级控制的简单，通用和高效的技术，但对于实现高性能的基于有机物的存储电子设备而言，却是非常困难的。在本文中，我们采用浸涂法来制造可靠且具有成本效益的有机存储设备（OMD）。该技术使我们能够在薄膜表面上沉积高质量，均匀且大面积的纳米图案，并实现均匀的OMD性能，记录再现性高达96％。据我们所知，这是迄今为止观察到的具有最高重现性的浸涂OMD的第一份报告，这证明了浸涂技术在制造有机存储器件方面具有广阔的前景，并且适用于大规模生产吞吐量解决方案处理。
• Selective Conversion of Levulinic and Formic Acids to γ-Valerolactone with the Shvo Catalyst
  作者：Viktória Fábos、László T. Mika、István T. Horváth

  DOI：10.1021/om400938h

  日期：2014.1.13

  The selective transfer hydrogenation of levulinic acid (LA) with formic acid (FA) to 4-hydroxyvaleric acid (4-HVA) and carbon dioxide followed by the intramolecular dehydration of 4-HVA to gamma-valerolactone (GVL) are key steps of the conversion of carbohydrate-based biomass to GVL, which can be used for the production of both energy and carbon-based products. LA was converted to GVL in the presence of a small excess of FA and the Shvo catalysts [2,5-Ph-2-3,4-(Ar)(2)(eta(5)-C4CO)](2)H}Ru-2(CO)(4)(mu-H)]} (Ar = p-MeOPh (1a), p-MePh (1b), Ph (1c)). The reactions were performed at 100 degrees C with yields higher than 99% after a few hours. The formation of 1,4-pentanediol and 2-methyltetrahydrofuran remained below detection limits. The only side products were water and carbon dioxide, as expected, which were easily removed and separated from the product GVL under reduced pressure. The Shvo catalyst 1c was recycled four times without losing catalytic activity, and the product GVL was isolated each time as a colorless liquid of 99.9% purity with only trace amounts of water present.