3-hydroxy-4-(4-methoxyphenyl)-1-methylquinolin-2(1H)-one | 1134192-63-4

• 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-(4-methoxyphenyl)-1-methylquinolin-2(1H)-one
• 英文别名: 1-Methyl-3-hydroxy-4-(4-methoxyphenyl)quinoline-2(1H)-one；3-hydroxy-4-(4-methoxyphenyl)-1-methylquinolin-2-one
• CAS: 1134192-63-4
• 化学式: C₁₇H₁₅NO₃
• mdl: MFCD30836083
• 分子量: 281.311
• InChiKey: YJALINLQHRDUIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-cyano-3-(4-methoxyphenyl)-N-methyl-N-phenyloxirane-2-carboxamide 在 硫酸 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以89%的产率得到3-hydroxy-4-(4-methoxyphenyl)-1-methylquinolin-2(1H)-one
  参考文献：
  名称：

  A Concise and Versatile Synthesis of Viridicatin Alkaloids from Cyanoacetanilides

  摘要：

  The efficient synthesis of 3-hydroxy-4-arylquinolin-2(1H)-ones through one-pot Knoevenagel condensation/epoxidation of cyanoacetanilides followed by decyanative epoxide-arene cyclization is described. A convergent assembly with functionalized aldehydes allows for rapid synthesis with diverse substitution patterns. Isolation of 3-hydroxy-4-arylquinolin-2(1H)-ones is readily accomplished by precipitation and filtration.

  DOI：

  10.1021/ol900255g

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。