1-[4-amino-3-(phenylethynyl)phenyl]ethanone | 1200659-75-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-amino-3-(phenylethynyl)phenyl]ethanone
• 英文别名: 1-[4-Amino-3-(2-phenylethynyl)phenyl]ethanone
• CAS: 1200659-75-1
• 化学式: C₁₆H₁₃NO
• 分子量: 235.285
• InChiKey: KAGNNAZWIGAQOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-amino-3-(phenylethynyl)phenyl]ethanone 以 水 为溶剂， 反应 1.5h， 以20%的产率得到1-(2-phenyl-1H-indol-5-yl)ethanone
  参考文献：
  名称：

  Microwave-assisted synthesis of indole-derivatives via cycloisomerization of 2-alkynylanilines in water without added catalysts, acids, or bases

  摘要：

  An unprecedented green methodology is described for the preparation of differently substituted indoles via microwave-assisted cycloisomerization of 2-alkynylaniline derivatives in water. Moderate to good yields in the cyclization can be achieved for a variety of 2-aminoaryl alkynes. Reactions are run without any added metal catalyst, acid, or base, and do not take place by applying conventional heating. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.135
• 作为产物：
  描述：

  苯乙炔 、 1-(4-氨基-3-碘苯基)乙酮 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 三乙胺 为溶剂， 反应 4.0h， 生成 1-[4-amino-3-(phenylethynyl)phenyl]ethanone
  参考文献：
  名称：

  Diaceno[a,e]pentalenes from Homoannulations of o-Alkynylaryliodides Utilizing a Unique Pd(OAc)₂/n-Bu₄NOAc Catalytic Combination

  摘要：

  A heterogeneous catalytic system, Pd(OAc)(2)/n-Bu4NOAc, for the efficient synthesis of diaceno[a,e)pentalenes via a tandem Pd catalytic cycle is reported. The catalytic partner n-Bu4NOAc played indispensable and versatile roles, acting as both the media for recovering active Pd(0) species and their stabilizer. A series of new diaceno[a,dpentalenes were obtained in moderate to high yields, among which the octacydic dianthracenopentalene was found to be highly emissive.

  DOI：

  10.1021/ol502440d

文献信息

• Microwave-assisted synthesis of indole-derivatives via cycloisomerization of 2-alkynylanilines in water without added catalysts, acids, or bases
  作者：Adriano Carpita、Arianna Ribecai

  DOI：10.1016/j.tetlet.2009.09.135

  日期：2009.12

  An unprecedented green methodology is described for the preparation of differently substituted indoles via microwave-assisted cycloisomerization of 2-alkynylaniline derivatives in water. Moderate to good yields in the cyclization can be achieved for a variety of 2-aminoaryl alkynes. Reactions are run without any added metal catalyst, acid, or base, and do not take place by applying conventional heating. (C) 2009 Elsevier Ltd. All rights reserved.
• Diaceno[<i>a</i>,<i>e</i>]pentalenes from Homoannulations of <i>o</i>-Alkynylaryliodides Utilizing a Unique Pd(OAc)₂/<i>n</i>-Bu₄NOAc Catalytic Combination
  作者：Junjian Shen、Dafei Yuan、Yan Qiao、Xingxing Shen、Zhongbo Zhang、Yuwu Zhong、Yuanping Yi、Xiaozhang Zhu

  DOI：10.1021/ol502440d

  日期：2014.9.19

  A heterogeneous catalytic system, Pd(OAc)(2)/n-Bu4NOAc, for the efficient synthesis of diaceno[a,e)pentalenes via a tandem Pd catalytic cycle is reported. The catalytic partner n-Bu4NOAc played indispensable and versatile roles, acting as both the media for recovering active Pd(0) species and their stabilizer. A series of new diaceno[a,dpentalenes were obtained in moderate to high yields, among which the octacydic dianthracenopentalene was found to be highly emissive.
• Microwave-assisted synthesis of indole- and azaindole-derivatives in water via cycloisomerization of 2-alkynylanilines and alkynylpyridinamines promoted by amines or catalytic amounts of neutral or basic salts
  作者：Adriano Carpita、Arianna Ribecai、Paolo Stabile

  DOI：10.1016/j.tet.2010.06.083

  日期：2010.8

  An efficient methodology is described and exploited for the preparation of differently substituted indoles and azaindoles via microwave-assisted cycloisomerization in water of 2-alkynylanilines and alkynylpyridinamines, which is promoted by catalytic amounts of neutral or basic salts or by stoichiometric weak organic bases. Good to high yields in the cyclization can be achieved for a variety of 2-amino (hetero)aryl alkynes. Reactions are run without any added metal catalyst. A comparison with the cycloisomerization conducted under conventional heating is also described. (C) 2010 Elsevier Ltd. All rights reserved.