1',7'-dihydro-5',5',7',7'-tetramethylspiro(1,3-dioxolane-2,4'-[4H]inden)-6'(5'H)-one | 174747-11-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 1',7'-dihydro-5',5',7',7'-tetramethylspiro(1,3-dioxolane-2,4'-[4H]inden)-6'(5'H)-one
• 英文别名: 4',4',6',6'-tetramethylspiro[1,3-dioxolane-2,7'-3H-indene]-5'-one
• CAS: 174747-11-6
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: AGOWGTIWMMKDLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1',7'-dihydro-5',5',7',7'-tetramethylspiro(1,3-dioxolane-2,4'-[4H]inden)-6'(5'H)-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 以85%的产率得到5,5,7,7-Tetramethyl-1,7-dihydro-indene-4,6-dione
  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：

  2-Cyclopentadienylidene-1,3-dioxolane 、 2,4-二溴-2,4-二甲基-3-戊酮 在 diiron nonacarbonyl 作用下， 以 苯 为溶剂， 反应 2.0h， 以86%的产率得到1',7'-dihydro-5',5',7',7'-tetramethylspiro(1,3-dioxolane-2,4'-[4H]inden)-6'(5'H)-one
  参考文献：
  名称：

  [6 + 3]富烯烯酮缩醛的环加成

  摘要：

  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。

  DOI：

  10.1016/0040-4039(95)02226-0

文献信息

• [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。
• Metal-Mediated [6 + 3] Cycloaddition Reactions of Fulvenes. A Novel Approach to Indan Systems
  作者：Bor-cherng Hong、Si-shoung Sun、Yann-chien Tsai

  DOI：10.1021/jo970984j

  日期：1997.10.1

  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.