2,5-dimethyl-1,3,4-triphenyl-cyclopentadiene | 67209-33-0

• 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: 2,5-dimethyl-1,3,4-triphenyl-cyclopentadiene
• 英文别名: 3,5-Dimethyl-1,2,4-triphenylcyclopenta-1,3-dien；(2,5-Dimethyl-3,4-diphenylcyclopenta-1,3-dien-1-yl)benzene
• CAS: 67209-33-0
• 化学式: C₂₅H₂₂
• 分子量: 322.45
• InChiKey: OKKPTFXANBWBGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,5-dimethyl-1,3,4-triphenyl-cyclopentadiene 在 2,3,4,5-四氟苯硼酸 作用下， 以 硝基甲烷 为溶剂， 反应 16.0h， 生成 (2,4-Dimethyl-3,5-diphenylcyclopenta-1,3-dien-1-yl)benzene
  参考文献：
  名称：

  Mild boronic acid catalyzed Nazarov cyclization of divinyl alcohols in tandem with Diels–Alder cycloaddition

  摘要：

  Boronic acid catalysis (BAC) was applied to a sequential Nazarov cyclization of divinyl alcohols/Diels-Alder cycloadditions leading to the preparation of highly functionalized bicyclic compounds in a highly diastereoselective fashion. In these one-pot transformations, highly functionalized dienes were generated in situ through boronic acid catalyzed Nazarov cyclizations of divinyl alcohols and were subsequently trapped with different dienophiles such as maleic anhydride and phenylmaleimide. The tandem reactions proceed directly from divinyl alcohols under very mild reaction conditions using air-stable catalysts, and as such this methodology represents a greener alternative to existing methods employing strong Lewis and Bronsted acids. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.100
• 作为产物：
  描述：

  2,5-dimethyl-3,4-diphenylcyclopent-2-en-1-one 在 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 2,5-dimethyl-1,3,4-triphenyl-cyclopentadiene
  参考文献：
  名称：

  Synthesis of Multisubstituted Cyclopentadienes from Cyclopentenones Prepared via Catalytic Double Aldol Condensation and Nazarov Reaction Sequence

  摘要：

  通过铼催化的双Aldol缩合反应及随后的Nazarov反应，描述了环戊烯酮衍生物的合成方法。环戊烯酮可利用有机锂试剂转化为相应的环戊二烯。通过逐步双Aldol缩合反应，以酮和两种醛为原料，随后用有机锂试剂处理，可以合成具有四种不同取代基的环戊二烯。

  DOI：

  10.1055/s-0030-1260324

文献信息

• Direct synthesis of polysubstituted cyclopentenones from ketones and aldehydes catalyzed by zirconium compounds
  作者：Tsuyoshi Yuki、Motochika Hashimoto、Yutaka Nishiyama、Yasutaka Ishii

  DOI：10.1021/jo00068a060

  日期：1993.7
• Base-catalyzed alkylation of cyclopentadiene rings with alcohols and amines
  作者：Stephen S. Hirsch、William J. Bailey

  DOI：10.1021/jo00415a022

  日期：1978.10
• HIRSCH S. S.; BAILEY W. J., J. ORG.CHEM., 1978, 43, NO 21, 4090-4094
  作者：HIRSCH S. S.、 BAILEY W. J.

  DOI：——

  日期：——
• Synthesis of Multisubstituted Cyclopentadienes from Cyclopentenones Prepared via Catalytic Double Aldol Condensation and Nazarov Reaction Sequence
  作者：Yoichiro Kuninobu、Kazuhiko Takai、Yuta Nishina、Tomohiro Tatsuzaki、Ayano Tsubakihara

  DOI：10.1055/s-0030-1260324

  日期：2011.10

  The rhenium-catalyzed synthesis of cyclopentenone derivatives via double aldol condensation and successive Nazarov reaction is described. The cyclopentenones were converted to the corresponding cyclopentadienes using organolithium reagents. Cyclopentadienes with four different substituents could be synthesized by stepwise double aldol condensation using a ketone and two types of aldehydes, followed by treatment with an organolithium reagent.

  通过铼催化的双Aldol缩合反应及随后的Nazarov反应，描述了环戊烯酮衍生物的合成方法。环戊烯酮可利用有机锂试剂转化为相应的环戊二烯。通过逐步双Aldol缩合反应，以酮和两种醛为原料，随后用有机锂试剂处理，可以合成具有四种不同取代基的环戊二烯。
• Mild boronic acid catalyzed Nazarov cyclization of divinyl alcohols in tandem with Diels–Alder cycloaddition
  作者：Hongchao Zheng、Michal Lejkowski、Dennis G. Hall

  DOI：10.1016/j.tetlet.2012.10.100

  日期：2013.1

  Boronic acid catalysis (BAC) was applied to a sequential Nazarov cyclization of divinyl alcohols/Diels-Alder cycloadditions leading to the preparation of highly functionalized bicyclic compounds in a highly diastereoselective fashion. In these one-pot transformations, highly functionalized dienes were generated in situ through boronic acid catalyzed Nazarov cyclizations of divinyl alcohols and were subsequently trapped with different dienophiles such as maleic anhydride and phenylmaleimide. The tandem reactions proceed directly from divinyl alcohols under very mild reaction conditions using air-stable catalysts, and as such this methodology represents a greener alternative to existing methods employing strong Lewis and Bronsted acids. (C) 2012 Elsevier Ltd. All rights reserved.