4-amino-2,3-dihydrocyclopenta[a]xanthen-11(1H)-one | 1415681-79-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-amino-2,3-dihydrocyclopenta[a]xanthen-11(1H)-one
• 英文别名: 4-amino-2,3-dihydro-1H-cyclopenta[a]xanthen-11-one
• CAS: 1415681-79-6
• 化学式: C₁₆H₁₃NO₂
• 分子量: 251.285
• InChiKey: CPCVAJXXHBQUCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(2-methyl-4-oxo-4H-chromen-3-yl)cyclopent-1-enecarbonitrile 在 3-溴氰苄 、 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以86%的产率得到4-amino-2,3-dihydrocyclopenta[a]xanthen-11(1H)-one
  参考文献：
  名称：

  An Organic Molecule Modulated Chemoselective Cyclization of Alkynyl Nitriles Tethered to 2-Alkyl Substituted Chromones with Multireactive Sites

  摘要：

  A small organic molecule phenylacetonitrile promoted chemoselective cyclization of (chromen-3-yl)alkynylnitriles to generate a novel tetracyclic or tricyclic chromone scaffold has been discovered. Importantly, the phenylacetonitrile serves as an anion transfer reagent changing the normal reaction of the substrate.

  DOI：

  10.1021/ol302964x

文献信息

• Phase Transfer Reagent Promoted Tandem Ring-Opening and Ring-Closing Reactions of Unique 3-(1-Alkynyl) Chromones
  作者：Yang Liu、Shiyu Jin、Liping Huang、Youhong Hu

  DOI：10.1021/acs.orglett.5b00721

  日期：2015.5.1

  promoted tandem ring-opening and ring-closing reaction of 3-(1-alkynyl) chromones has been developed. This process remarkably generates functionalized 3-acyl-2-substituted chromones. Interestingly, when 3-(hepta-1,6-diyn-1-yl)chromone derivatives are applied, a novel tetracyclic chromone scaffold can be obtained by a further intramolecular 4 + 2 cyclization.

  已经开发出相转移试剂促进3-（1-炔基）色酮的串联开环和闭环反应。该过程显着产生官能化的3-酰基-2-取代的色酮。有趣的是，当使用3-（庚-1,6-二炔-1-基）色酮衍生物时，可以通过进一步的分子内4 + 2环化获得新型的四环色酮支架。
• An Organic Molecule Modulated Chemoselective Cyclization of Alkynyl Nitriles Tethered to 2-Alkyl Substituted Chromones with Multireactive Sites
  作者：Liping Huang、Yang Liu、Fuchun Xie、Youhong Hu

  DOI：10.1021/ol302964x

  日期：2012.12.21

  A small organic molecule phenylacetonitrile promoted chemoselective cyclization of (chromen-3-yl)alkynylnitriles to generate a novel tetracyclic or tricyclic chromone scaffold has been discovered. Importantly, the phenylacetonitrile serves as an anion transfer reagent changing the normal reaction of the substrate.