2-benzyl-5-benzylidenecyclopentanone | 23911-64-0

• 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: 2-benzyl-5-benzylidenecyclopentanone
• 英文别名: (+/-)-3-Benzyl-1-benzyliden-cyclopentan-2-on；(5E)-2-benzyl-5-benzylidenecyclopentan-1-one
• CAS: 23911-64-0
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: PVAYOBPFYZHJKI-GHRIWEEISA-N

物化性质

• 沸点：
  428.1±25.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  2-benzyl-5-benzylidenecyclopentanone 以 甲醇 、 水 为溶剂， 反应 65.5h， 生成 2.9-Dibenzyl-6.12-diphenyl-dispiro-<4.1.4.1>dodecan-1.8-dion
  参考文献：
  名称：

  固态光二聚反应的静态和动态单晶X射线衍射研究

  摘要：

  DOI：

  10.1021/j150624a022
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 镍 作用下， 生成 2-benzyl-5-benzylidenecyclopentanone
  参考文献：
  名称：

  Cornubert et al., Bulletin de la Societe Chimique de France, 1938, vol. <5> 5, p. 534,535, 536, 540

  摘要：

  DOI：

文献信息

• Photodimerisation of 2-benzyl-5-benzylidenecyclopentanone
  作者：G. C. Forward、D. A. Whiting

  DOI：10.1039/j39690001868

  日期：——

  The title compound yields a photodimer on u.v. irradiation, and not a phototrimer as described in the literature. This dimer has been shown to be 2,9-dibenzyl-6,12-diphenyl-dispiro[4.1.4.1]dodecan-1,8-dione (XII); its stereochemistry has been elucidated by chemical and spectroscopic methods.

  标题化合物在紫外线照射下产生光二聚体，而不是文献中所述的光三聚体。已经表明该二聚体是2，9-二苄基-6，12-二苯基-二螺[4.1.4.1] dodecan-1，8-二酮（XII）； m。其立体化学已通过化学和光谱方法阐明。
• Monitoring the crystallographic course of a single-crystal ? single-crystal photodimerization by X-ray diffractometry
  作者：Hachiro Nakanish、William Jones、John M. Thomas、Michael B. Hursthouse、Majid Motevalli

  DOI：10.1039/c39800000611

  日期：——

  Using four-circle diffractometry in a dynamic mode, the course of the topochemical photodimerization of 2-benzyl-5-benzylidenecyclopentanone has been determined.

  在动态模式下使用四圆衍射法，已经确定了2-苄基-5-亚苄基环戊酮的拓扑化学光二聚化过程。
• Structural Transformations in a Crystal during the Photochemical Reaction of 2-Benzyl-5-benzylidenecyclopentanone
  作者：Ilona Turowska-Tyrk

  DOI：10.1002/1521-3765(20010803)7:15<3401::aid-chem3401>3.0.co;2-f

  日期：2001.8.3

  presented are the first example in which the substrate and product molecules were monitored separately over many stages during the chemical reaction progress in a crystal to understand the reaction path of the molecules in detail during the whole transformation. The BBCP, 2-benzyl-5-benzylidenecyclopentanone, single crystal was irradiated without any destruction over several steps. After each of step

  提出的研究是第一个实例，其中在晶体化学反应过程中的多个阶段分别监控底物和产物分子，以详细了解整个转化过程中分子的反应路径。BBCP 2-苄基-5-亚苄基环戊酮单晶经过数步辐照而没有任何破坏。在每个步骤之后，确定具有不同底物/产物比率和无序的X射线结构。研究表明，晶体中BBCP的光化学[2 + 2]-环加成反应不表现出协同特性，可以被认为是一阶的。在转化过程中，产物分子未采用分子在最终纯二聚体晶体中的位置，但朝这个方向逐渐平稳地移动。还观察到了底物分子的运动。产物和反应物分子的这种显着行为带有旋转分量。相邻BBCP底物分子的反应中心之间的距离随着反应的进行而顺畅地减小，但不小于范德华半径之和。
• Mayer, Chemische Berichte, 1955, vol. 88, p. 1853,1857
  作者：Mayer

  DOI：——

  日期：——
• ——
  作者：Haitao Chen、Zhizhong Ji、Lan K. Wong、Jerome F. Siuda、Ven L. Narayanan

  DOI：10.1023/a:1016067210281

  日期：——

  Purpose. A series of 2-substituted-2-dimethylaminomethyl-5-(E)-arylidene cyclopentanones, 4 were synthesized. The main objective of this investigation was to explore the structural parameters necessary for antiinflammatory activity in this series of compounds, while keeping cytotoxic action to a minimum.Methods. The target compounds were synthesized in two steps commencing with 2-alkyl-cyclopentanones. Antiinflammatory, analgesic and cytotoxic activities were determined in rats. Cytotoxic results were examined in human cell lines.Results. Eight of the eighteen synthetic substances possessed significant antiinflammatory activity and twelve showed appreciable analgesic action. Cytotoxicity was minimal or nonexistent for most of the compounds. The stability of one of the compounds, 4b in both aqueous and non-aqueous media, and an amine exchange reaction with aniline wee used to explain the observed antiinflammatory and cytotoxic activities.Conclusions. Unlike monosubstituted aminomethyl groups (Mannich bases) at the 2-position of 5-arylidene-2-cyclopentanones, a second substituent at the 2-position increases stability of the Mannich base and significantly decreases cytotoxic activity, Antiinflammatory and analgesic action is retained in many of the compounds, thus strongly indicating that these desired pharmacological results can be obtained without untoward damage to cells.