4-[(4-methoxyphenyl)amino]-6-phenyl-2H-pyran-2-one | 1304104-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[(4-methoxyphenyl)amino]-6-phenyl-2H-pyran-2-one
• 英文别名: 4-(4-Methoxyanilino)-6-phenylpyran-2-one
• CAS: 1304104-58-2
• 化学式: C₁₈H₁₅NO₃
• 分子量: 293.322
• InChiKey: KKGIMOJRNPWEIQ-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：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(4-methoxyphenyl)amino]-6-phenyl-2H-pyran-2-one 在 silver(I) acetate 、 palladium diacetate 、 溶剂黄146 作用下， 反应 16.0h， 以94%的产率得到8-methoxy-3-phenylpyrano[4,3-b]indol-1(5H)-one
  参考文献：
  名称：

  Access to Indole-Fused Polyheterocycles via Pd-Catalyzed Base-Free Intramolecular Cross Dehydrogenative Coupling

  摘要：

  A base-free process to access indole-fused polyheterocycles via a highly efficient and atom-economic palladium-catalyzed intramolecular cross dehydrogenetive coupling (CDC) reaction of 4-aniline substituted coumarins, quinolinones, and pyrones has been developed. A wide range of indolo[3,2-c]coumarins, indolo[3,2-c]quinolinones, and indolo[3,2-c]pyrones can be facilely afforded in good to excellent yields (up to 99%).

  DOI：

  10.1021/acs.joc.6b02160
• 作为产物：
  描述：

  4-羟基-6-苯基吡喃-2-酮 在 三乙胺 、 三氯氧磷 作用下， 以 乙二醇 为溶剂， 反应 2.0h， 生成 4-[(4-methoxyphenyl)amino]-6-phenyl-2H-pyran-2-one
  参考文献：
  名称：

  Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity

  摘要：

  4-Amino-2H-benzo[h] chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H-benzo[h] chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 mu M. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.084

文献信息

• Antitumor agents 287. Substituted 4-amino-2H-pyran-2-one (APO) analogs reveal a new scaffold from neo-tanshinlactone with in vitro anticancer activity
  作者：Yizhou Dong、Kyoko Nakagawa-Goto、Chin-Yu Lai、Susan L. Morris-Natschke、Kenneth F. Bastow、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2011.02.084

  日期：2011.4

  4-Amino-2H-benzo[h] chromen-2-one (ABO) and 4-amino-7,8,9,10-tetrahydro-2H-benzo[h] chromen-2-one (ATBO) analogs were found to be significant in vitro anticancer agents in our previous research. Our continuing study has now discovered a new simplified (monocyclic rather than tricyclic) class of cytotoxic agents, 4-amino-2H-pyran-2-one (APO) analogs. By incorporating various substituents on the pyranone ring, we have established preliminary structure-activity relationships (SAR). Analogs 19, 20, 23, and 26-30 displayed significant tumor cell growth inhibitory activity in vitro. The most active compound 27 exhibited ED50 values of 0.059-0.090 mu M. (C) 2011 Elsevier Ltd. All rights reserved.
• Access to Indole-Fused Polyheterocycles via Pd-Catalyzed Base-Free Intramolecular Cross Dehydrogenative Coupling
  作者：Chao Cheng、Wen-Wen Chen、Bin Xu、Ming-Hua Xu

  DOI：10.1021/acs.joc.6b02160

  日期：2016.11.18

  A base-free process to access indole-fused polyheterocycles via a highly efficient and atom-economic palladium-catalyzed intramolecular cross dehydrogenetive coupling (CDC) reaction of 4-aniline substituted coumarins, quinolinones, and pyrones has been developed. A wide range of indolo[3,2-c]coumarins, indolo[3,2-c]quinolinones, and indolo[3,2-c]pyrones can be facilely afforded in good to excellent yields (up to 99%).