2-Cyclopentadienylidene-1,3-dioxolane | 67399-79-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-Cyclopentadienylidene-1,3-dioxolane
• 英文别名: 2-cyclopentadienyliden-1,3-dioxolane；2-Cyclopentadienyliden-1,3-dioxacyclopentan；2-Cyclopenta-2,4-dien-1-ylidene-1,3-dioxolane
• CAS: 67399-79-5
• 化学式: C₈H₈O₂
• 分子量: 136.15
• InChiKey: KNRWXUMFNFEPBS-UHFFFAOYSA-N

物化性质

• 沸点：
  268.9±20.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Cyclopentadienylidene-1,3-dioxolane 在 lithium aluminium tetrahydride 、 diiron nonacarbonyl 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 2.0h， 生成 C₁₃H₁₈O₃
  参考文献：
  名称：

  Metal-Mediated [6 + 3] Cycloaddition Reactions of Fulvenes. A Novel Approach to Indan Systems

  摘要：

  The [6 + 3] cycloaddition of 2-oxyallyl cations to the electron rich fulvene ketene acetal provides an efficient route to the indan skeleton. The structures of these indan adducts were assigned by extensive 2D NMR experiments. Direct hydrolysis of these ketal adducts affords the corresponding diketones or indens. Reaction of the fulvene ketene thioacetal as well as the tandem [6 + 3]-[4 + 3] cycloadditions were also studied. A mechanism is proposed which may account for the origin of stereo-and regioselectivity in this cycloaddition.

  DOI：

  10.1021/jo970984j
• 作为产物：
  描述：

  环戊二烯 、 氯甲酸氯乙酯 生成 2-Cyclopentadienylidene-1,3-dioxolane
  参考文献：
  名称：

  2-环戊二烯基-1,3-二氧戊环的简单且经济高效的合成

  摘要：

  摘要 实现了以环戊二烯和氯甲酸2-氯乙酯为原料高效制备2-环戊二烯基-1,3-二氧戊环的方法。两当量的环戊二烯化钠和 KOH 与 0.1 M 的氯甲酸 2-氯乙酯的反应产生最高产率的富烯。

  DOI：

  10.1080/00397919708005639

文献信息

• An improved pathway to 6,6-disubstituted fulvenes
  作者：Khalil Chajara、Henrik Ottosson

  DOI：10.1016/j.tetlet.2004.07.058

  日期：2004.8

  Pentafulvenes with alkyl and/or aryl substituents at the exocyclic position are formed rapidly in high yields through reaction of crystalline sodium cyclopentadienide directly with the appropriate ketones.

  通过使环戊二烯酸钠结晶与合适的酮直接反应，可以高收率快速形成在环外位置具有烷基和/或芳基取代基的五叶黄酮。
• Facile synthesis of azulenols: [6 + 4] cycloadditions of fulveneketene acetal
  作者：Bor-Cherng Hong、Si-Shoung Sun

  DOI：10.1039/cc9960000937

  日期：——

  In contrast to the Diels–Alder reaction of fulvenes and pyrones, fulveneketene acetal reacts with α-pyrone to give the [6 + 4] cycloaddition adduct, an efficient and novel route to the azulenols.

  与富烯和吡喃酮的 Diels-Alder 反应相反，富烯酮缩醛与 α-吡喃酮反应生成 [6 + 4] 环加成加合物，这是一种高效且新颖的制备薁醇的途径。
• [6+3] Cycloaddition of fulveneketene acetal
  作者：Bor-Cherng Hong、Si-shoung Sun

  DOI：10.1016/0040-4039(95)02226-0

  日期：1996.1

  A novel [6+3] cycloaddition of 2-oxyallyl cation and fulveneketene acetal is described which provides a conceptually novel methodology for the synthesis of indan ring systems.

  描述了2-氧烯丙基阳离子和富烯烯酮缩醛的新型[6 + 3]环加成反应，其为合成茚满环系统提供了概念上新颖的方法。
• Hong, Bor-Cherng; Chen, Zhong-Yi; Sampath Kumar, Journal of the Chemical Society. Perkin transactions I, 1999, # 9, p. 1135 - 1137
  作者：Hong, Bor-Cherng、Chen, Zhong-Yi、Sampath Kumar

  DOI：——

  日期：——
• Microwave-assisted [6+4]-cycloaddition of fulvenes and α-pyrones to azulene–indoles: Facile syntheses of novel antineoplastic agents
  作者：Bor-Cherng Hong、Yea-Fen Jiang、Ellappan Sampath Kumar

  DOI：10.1016/s0960-894x(01)00349-3

  日期：2001.8

  A microwave-enhanced [6 + 4]-cycloaddition reaction between 6-aminofulvene and pyrones followed by CO2 extrusion provides azulene-indoles which display interesting antineoplastic activity. (C) 2001 Elsevier Science Ltd. All rights reserved.

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