4-oxo-9-phenyl-2,3,3a,4-tetrahydro-1H-cyclopenta[b]naphthalene-3α-carbonitrile | 1415336-93-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基四氢萘木脂素
• 英文名称: 4-oxo-9-phenyl-2,3,3a,4-tetrahydro-1H-cyclopenta[b]naphthalene-3α-carbonitrile
• 英文别名: 4-oxo-9-phenyl-2,3,3α,4-tetrahydro-1H-cyclopenta[b]naphthalene-3α-carbonitrile；4-oxo-9-phenyl-2,3-dihydro-1H-cyclopenta[b]naphthalene-3a-carbonitrile
• CAS: 1415336-93-4
• 化学式: C₂₀H₁₅NO
• 分子量: 285.345
• InChiKey: ASCNASCWGPLAFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-benzoyl-7-phenylhept-6-ynenitrile 在 叔丁基过氧化氢 、 四丁基碘化铵 作用下， 以 水 、 苯 为溶剂， 反应 1.0h， 以85%的产率得到4-oxo-9-phenyl-2,3,3a,4-tetrahydro-1H-cyclopenta[b]naphthalene-3α-carbonitrile
  参考文献：
  名称：

  Tandem Cyclization of α-Cyano α-Alkynyl Aryl Ketones Induced by tert-Butyl Hydroperoxide and Tetrabutylammonium Iodide

  摘要：

  The radical cascade protocol of the alpha-cyano alpha-TMS/aryl-capped alkynyl aryl ketones promoted by tert-butyl hydroperoxide under catalysis with tetrabutylammonium iodide in refluxing benzene has been developed, leading to the construction of a variety of highly functionalized [6,6,5] tricyclic frameworks in an efficient manner.

  DOI：

  10.1021/ol3028972

文献信息

• Palladium(0)/Copper(I)-Catalyzed Tandem Cyclization of Aryl 1-Cyanoalk-5-ynyl Ketone System: Rapid Assembly of Cyclopenta[<i>b</i>]naphthalene and Benzo[<i>b</i>]fluorene Derivatives
  作者：Ying-Chieh Wong、Tzu-Ting Kao、Yu-Cheng Yeh、Bing-Siou Hsieh、Kak-Shan Shia

  DOI：10.1002/adsc.201300107

  日期：2013.5.3

  cyclopenta‐[b]naphthalene derivatives via the palladium(0)/copper(I)‐catalyzed tandem cyclization of aryl 1‐cyanoalk‐5‐ynyl ketone systems in an extremely efficient manner. The key operation lies in the copper(I)‐catalyzed aerobic oxidation, which allows for activation of two successive intramolecular cycloadditions immediately after the Sonogashira coupling reaction has occurred.

  我们已经开发出一种新的通用方法，可通过钯（0）/铜（I）催化的芳基1-氰基烷基-5-炔基的串联环化反应来构建各种苯并[ b ]芴和环戊[ b ]萘衍生物。酮系统的效率极高。关键操作在于铜（I）催化的好氧氧化，该反应可在Sonogashira偶联反应发生后立即激活两个连续的分子内环加成反应。
• Tandem Cyclization of α-Cyano α-Alkynyl Aryl Ketones Induced by <i>tert</i>-Butyl Hydroperoxide and Tetrabutylammonium Iodide
  作者：Ying-Chieh Wong、Chen-Tso Tseng、Tzu-Ting Kao、Yu-Cheng Yeh、Kak-Shan Shia

  DOI：10.1021/ol3028972

  日期：2012.12.7

  The radical cascade protocol of the alpha-cyano alpha-TMS/aryl-capped alkynyl aryl ketones promoted by tert-butyl hydroperoxide under catalysis with tetrabutylammonium iodide in refluxing benzene has been developed, leading to the construction of a variety of highly functionalized [6,6,5] tricyclic frameworks in an efficient manner.