3-phenylamino-5-bromo-2-pyrone | 515179-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-phenylamino-5-bromo-2-pyrone
• 英文别名: 3-Anilino-5-bromopyran-2-one
• CAS: 515179-36-9
• 化学式: C₁₁H₈BrNO₂
• 分子量: 266.094
• InChiKey: JSRITWFDOCAFFW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenylamino-5-bromo-2-pyrone 在 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 生成
  参考文献：
  名称：

  Diels–Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives

  摘要：

  3-Phenylamino-5-bromo-2-pyrone undergoes facile Diels-Alder cycloadditions with various electron deficient dienophiles to afford an array of functionally rich and stereochemically defined cycloadducts in good to excellent isolated yields. Due to the electron donacity 4 the amine group, it only proceeds in normal electron demand D-A cycloadditions. Subsequent ring openings with NaOMe provided constrained a-amino acid derivatives. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.12.097
• 作为产物：
  描述：

  苯胺 、 3,5-二溴-2H-吡喃-2-酮 在 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以82%的产率得到3-phenylamino-5-bromo-2-pyrone
  参考文献：
  名称：

  Regioselective palladium-catalyzed aminations of 3,5-dibromo-2-pyrone with various aryl and alkyl amines

  摘要：

  3,5-Dibromo-2-pyrone underwent facile palladium-catalyzed coupling reactions with various primary and secondary alkyl and aryl amines to furnish a variety of the previously unknown 3-arylamino- and 3-alkylamino-5-bromo-2-pyrones with good to excellent regioselectivity and chemical yields. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02484-x

文献信息

• Diels–Alder cycloadditions of 3-phenylamino-5-bromo-2-pyrone for the synthesis of constrained α-amino acid derivatives
  作者：Won-Suk Kim、Jin-Hee Lee、Jongmin Kang、Cheon-Gyu Cho

  DOI：10.1016/j.tetlet.2003.12.097

  日期：2004.2

  3-Phenylamino-5-bromo-2-pyrone undergoes facile Diels-Alder cycloadditions with various electron deficient dienophiles to afford an array of functionally rich and stereochemically defined cycloadducts in good to excellent isolated yields. Due to the electron donacity 4 the amine group, it only proceeds in normal electron demand D-A cycloadditions. Subsequent ring openings with NaOMe provided constrained a-amino acid derivatives. (C) 2004 Elsevier Ltd. All rights reserved.
• Regioselective palladium-catalyzed aminations of 3,5-dibromo-2-pyrone with various aryl and alkyl amines
  作者：Jin-Hee Lee、Cheon-Gyu Cho

  DOI：10.1016/s0040-4039(02)02484-x

  日期：2003.1

  3,5-Dibromo-2-pyrone underwent facile palladium-catalyzed coupling reactions with various primary and secondary alkyl and aryl amines to furnish a variety of the previously unknown 3-arylamino- and 3-alkylamino-5-bromo-2-pyrones with good to excellent regioselectivity and chemical yields. (C) 2002 Elsevier Science Ltd. All rights reserved.