3-hydroxy-4-(3-methoxyphenyl)quinolin-2(1H)-one | 94298-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-hydroxy-4-(3-methoxyphenyl)quinolin-2(1H)-one
• 英文别名: 3-hydroxy-4-(3-methoxy-phenyl)-1H-quinolin-2-one；3'-O-Methyl-viridicatol
• CAS: 94298-63-2
• 化学式: C₁₆H₁₃NO₃
• 分子量: 267.284
• InChiKey: FQYWYCNWHYJURY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  62.32
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-(3-methoxyphenyl)-3-oxo-N-phenylpropanamide 在 硫酸 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 二氯甲烷 为溶剂， 反应 3.2h， 生成 3-hydroxy-4-(3-methoxyphenyl)quinolin-2(1H)-one
  参考文献：
  名称：

  One-Pot Synthesis of 3-Hydroxyquinolin-2(1H)-ones from N-Phenylacetoacetamide via PhI(OCOCF₃)₂-Mediated α-Hydroxylation and H₂SO₄-Promoted Intramolecular Cyclization

  摘要：

  A clean, one-pot synthesis of the biologically important 3-hydroxyquinolin-2(1H)-one compounds has been realized from the readily available N-phenylacetoacetamide derivatives through a PhI(OCOCF3)(2)-mediated alpha-hydroxylation and a H2SO4-promoted intramolecular condensation. The hydroxyl group in the generated alpha-hydroxylated intermediate can be well tolerated in the second H2SO4-promoted cyclization step.

  DOI：

  10.1021/jo400541s

文献信息

• Regioselective Ring Expansion of Isatins with <i>In Situ</i> Generated α-Aryldiazomethanes: Direct Access to Viridicatin Alkaloids
  作者：Yellaiah Tangella、Kesari Lakshmi Manasa、Namballa Hari Krishna、B. Sridhar、Ahmed Kamal、Bathini Nagendra Babu

  DOI：10.1021/acs.orglett.8b01417

  日期：2018.6.15

  A novel efficient one-pot regioselective ring-expansion reaction of isatins with in situ generated α-aryl/heteroaryldiazomethanes for the construction of viridicatin alkaloids has been described under metal-free conditions. The utility of this protocol is further demonstrated in the synthesis of naturally occurring viridicatin, viridicatol, and substituted 3-O-methyl viridicatin and their scale up

  在无金属条件下，已经描述了一种新型的靛红与原位生成的α-芳基/杂芳基重氮甲烷的有效的一锅区域选择性环扩环反应，用于构建ridicatin的生物碱。该协议的效用在天然存在的viridicatin，viridicatol和取代的3- O-甲基viridicatin的合成及其规模放大中得到了进一步证明。