3-phenyl-5H-<1>benzopyrano<4,3-b>pyridine | 139584-93-3

• 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: 3-phenyl-5H-<1>benzopyrano<4,3-b>pyridine
• 英文别名: 3-phenyl-5H-benzopyrano[4,3-b]pyridine；3-phenyl-5H-chromeno[4,3-b]pyridine
• CAS: 139584-93-3
• 化学式: C₁₈H₁₃NO
• 分子量: 259.307
• InChiKey: HHQGNXNODCGHPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(2-丙炔氧基)苯甲醛 以 氯仿 、 xylene 为溶剂， 反应 84.0h， 生成 3-phenyl-5H-<1>benzopyrano<4,3-b>pyridine
  参考文献：
  名称：

  Synthesis of Aza Polycyclic Compounds Derived from Pyrrolidine, Indolizidine, and Indole via Intramolecular Diels−Alder Cycloadditions of Neutral 2-Azadienes

  摘要：

  A method for the preparation of novel oxaza and diaza polycyclic 9-oxa-4-azaphenanthrene, 5H-pyrido[2,3-alpha]pyrrolizine, 5H,6H-pyrido[3,2-g]indolizine, and 5H,6H-indeno[2,1-alpha]indole is described, based on tandem reactions: aza-Wittig reaction of N-vinylic phosphazenes with functionalized aldehydes and an intramolecular aza-Diels-Alder reaction.

  DOI：

  10.1021/jo016325v

文献信息

• Intramolecular Diels-Alder reactions of pyrimidines and a computational study toward their structure and reactivity
  作者：Werner A. W. Stolle、August E. Frissen、Antonius T. M. Marcelis、Henk C. Van der Plas

  DOI：10.1021/jo00037a011

  日期：1992.5

  The syntheses of 2-[(prop-2-ynyloxy)carbonyl]pyrimidine (1), 5-[(prop-2-ynyloxy)carbonyl]pyrimidine (2), 5-phenyl-2-[2-(1-prop-2-ynylpyrryl)]pyrimidine (8),5-phenyl-2-[2-(1-prop-2-ynylpyrrolidinyl)]pyrimidine (9) and 2-[2-(prop-2-ynyloxy)phenyl]-4,6-R2-5-R1-pyrimidine (R1 = H, Cl, Ph; R2 = H, Me) (14a-d) are described. Upon heating, the compounds 1, 9, and 14 undergo an intramolecular Diels-Alder reaction and a subsequent retro Diels-Alder reaction to yield the annelated pyridines 15, 16, and 17, respectively. The compounds 2 and 8 did not react. The nonreactivity of the compounds 2 and 8 is ascribed to conjugation of the pyrimidine aromatic system with part of the dienophilic side chain, giving rise to conformations in which the diene and dienophile moieties cannot interact. For the compounds 1, 9, and 14 conjugation is absent, due to steric hindrance. To support this, semiempirical (MDNO-PM3) and molecular mechanics (MMX, CHEMX) calculations were performed. The HOMO-LUMO energy separation of the compounds did not consequently reflect the observed reactivity. However, the probability of the compounds to be in a reactive conformation appeared to correlate with the observed rate of reaction (9 > 14a > 1 >> 2, 8).
• Synthesis of Aza Polycyclic Compounds Derived from Pyrrolidine, Indolizidine, and Indole via Intramolecular Diels−Alder Cycloadditions of Neutral 2-Azadienes
  作者：Francisco Palacios、Concepción Alonso、Patricia Amezua、Gloria Rubiales

  DOI：10.1021/jo016325v

  日期：2002.3.1

  A method for the preparation of novel oxaza and diaza polycyclic 9-oxa-4-azaphenanthrene, 5H-pyrido[2,3-alpha]pyrrolizine, 5H,6H-pyrido[3,2-g]indolizine, and 5H,6H-indeno[2,1-alpha]indole is described, based on tandem reactions: aza-Wittig reaction of N-vinylic phosphazenes with functionalized aldehydes and an intramolecular aza-Diels-Alder reaction.