α,α'-dicyclopentenyl ketone | 58866-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,α'-dicyclopentenyl ketone
• 英文别名: bis(1,2-cyclopentene)methanone；dicyclopent-1-enyl ketone；Di-cyclopent-1-enyl-keton；Di(cyclopenten-1-yl)methanone
• CAS: 58866-22-1
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: JTHVVAXWTIDCJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  α,α'-dicyclopentenyl ketone 在 乙醇 、 铂 作用下， 生成 二环戊基甲酮
  参考文献：
  名称：

  383.分子重排研究。第六部分 合成和oxotropic重排在环戊烯系列

  摘要：

  DOI：

  10.1039/jr9510001755
• 作为产物：
  描述：

  1-(cyclopenten-1-yl)-2-dimethoxyphosphoryl-3-hydroxypropan-1-one 在 盐酸 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 20.0h， 生成 α,α'-dicyclopentenyl ketone
  参考文献：
  名称：

  A new approach to cyclopentane annulated compounds via 1-(cyclopent-1-enylcarbonyl)vinylphosphonates

  摘要：

  含有两个或三个五元环的稠环系统是利用 1-(环戊-1-烯基羰基)乙烯基膦酸酯构建的，该膦酸酯可用作多功能成环试剂。

  DOI：

  10.1039/c39920000190

文献信息

• Olefination of α,α′-Divinyl Ketones through Catalytic Meyer−Schuster Rearrangement
  作者：Curtis J. Rieder、Karl J. Winberg、F. G. West

  DOI：10.1021/jo101497f

  日期：2011.1.7

  followed by catalytic Meyer−Schuster rearrangement has been developed for the olefination of 1,4-pentadien-3-ones to afford [3]dendralenes. Many of the traditional methods for the Meyer−Schuster rearrangement of alkynyl carbinols are not suitable with these highly unsaturated substrates because of their acid sensitivity. Unexpected reactivity during attempted rearrangement, including Nazarov-type electrocyclizations

  1,4-二烯-3-酮的直接烯烃化仍然是一个合成难题。已经开发出了两步方案，采用乙炔加成，然后进行催化的Meyer-Schuster重排，以实现1,4-戊二烯-3-酮的烯化反应，从而制得[3]树枝状烯烃。炔基甲醇的迈耶-舒斯特重排的许多传统方法由于其对酸的敏感性而不适用于这些高度不饱和的底物。提出了包括Nazarov型电环化在内的尝试重排过程中的意外反应性，以及利用催化VO（acac）2促进乙氧基乙炔加合物的Meyer-Schuster重排的条件。
• Construction of aryl-substituted triquinanes through the interrupted Nazarov reaction
  作者：Curtis J. Rieder、Ryan J. Fradette、F. G. West

  DOI：10.1039/b800800k

  日期：——

  The first examples of intermolecular trapping of Nazarov cyclopentenyl cation intermediates by simple arenes to furnish alpha-arylcyclopentanones are described.

  描述了通过简单的芳烃分子间捕获Nazarov环戊烯基阳离子中间体以提供α-芳基环戊烯酮的第一个实例。
• Heteroaromatic Trapping of Tricyclic 2-Oxidocyclopentenyl Cations: A Surprisingly Efficient Example of Intermolecular Interrupted Nazarov Reaction
  作者：Frederick G. West、Curtis J. Rieder、Ryan J. Fradette

  DOI：10.3987/com-09-s(s)132

  日期：——

  Bis(cycloalkenyl) ketones 2a and 2f underwent Nazarov cyclization and intermolecular trapping by electrophilic aromatic substitution with furans, thiophenes, pyrroles, indoles and dimethoxybenzene. Only the cis-anti-cis diastereomer was isolated with dicyclopentenyl ketone 2a, whereas a mixture of diastereomers was seen with 2f (albeit with complete regioselectivity). Comparable interrupted Nazarov trapping was not seen with acyclic dienones 2b-e, indicating the possible involvement of conformation effects in the polycyclic intermediates derived from 2a and 2f.
• Minami, Toru; Nakayama, Minoru; Fujimoto, Kouichi, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 75, # 1-4, p. 135 - 138
  作者：Minami, Toru、Nakayama, Minoru、Fujimoto, Kouichi、Matsuo, Shingo

  DOI：——

  日期：——
• Homologous Mukaiyama Reactions via Trapping of the Nazarov Intermediate with Silyloxyalkenes
  作者：Yen-Ku Wu、Robert McDonald、F. G. West

  DOI：10.1021/ol201125h

  日期：2011.7.15

  Treatment of 1,4-pentadien-3-ones and silyloxyalkenes with BF3 center dot OEt2 at room temperature or lower initiates a domino process consisting of sequential 4 pi electrocyclization and capture of the resulting cyclopentenyl cation by the electron-rich trap. The overall process furnishes 1,4-dicarbonyl products containing highly substituted cyclopentanones in good yields and with the establishment of up to five new stereocenters.