3-benzyl-5-chloro-4-hydroxy-8-methyl-1H-quinolin-2-one | 220462-68-0

• 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-benzyl-5-chloro-4-hydroxy-8-methyl-1H-quinolin-2-one
• CAS: 220462-68-0
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: QRTHGPIYMXGHCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzyl-5-chloro-4-hydroxy-8-methyl-1H-quinolin-2-one 在 吡啶 、 过氧乙酸 、 sodium hydroxide 作用下， 以 氯仿 、 溶剂黄146 、 xylene 、 苯 为溶剂， 反应 10.67h， 生成 (Z)-3a-benzyl-9-chloro-4-ethoxycarbonylmethylene-6-methyl-2,3a,4,5-tetrahydrofuro<2,3-c>quinolin-2-one
  参考文献：
  名称：

  Unprecedented Reactivity of 5-Substituted 3-Hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones with Ethyl (Triphenylphosphoranylidene)acetate

  摘要：

  3,5,8-Trisubstituted 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones (3) reacted with ethyl (triphenylphosphoranylidene)acetate (4) to yield several products. The major products, 4,7-disubstituted 1,3-dihydro-3-phenylacetoxy-2H-indol-2-ones (5) and (11), were formed via the molecular rearrangement of 3, catalyzed by the strongly basic Wittig reagent. The Wittig reaction at the lactam group of 3, resulting in 2-ethoxycarbonylmethylene derivatives, can be explained by the poor reactivity of the sterically hindered 4-oxo group. Under acid catalysis, the Wittig reaction proceeded at the hindered 4-oxo group as well. A series of minor products were also obtained through the Wittig reaction of 3. A reaction mechanism of the molecular rearrangement of substances (3) is proposed.

  DOI：

  10.3987/com-98-8305
• 作为产物：
  描述：

  苄基丙二酸二乙酯 、 5-氯邻甲苯胺 以43%的产率得到3-benzyl-5-chloro-4-hydroxy-8-methyl-1H-quinolin-2-one
  参考文献：
  名称：

  Unprecedented Reactivity of 5-Substituted 3-Hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones with Ethyl (Triphenylphosphoranylidene)acetate

  摘要：

  3,5,8-Trisubstituted 3-hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones (3) reacted with ethyl (triphenylphosphoranylidene)acetate (4) to yield several products. The major products, 4,7-disubstituted 1,3-dihydro-3-phenylacetoxy-2H-indol-2-ones (5) and (11), were formed via the molecular rearrangement of 3, catalyzed by the strongly basic Wittig reagent. The Wittig reaction at the lactam group of 3, resulting in 2-ethoxycarbonylmethylene derivatives, can be explained by the poor reactivity of the sterically hindered 4-oxo group. Under acid catalysis, the Wittig reaction proceeded at the hindered 4-oxo group as well. A series of minor products were also obtained through the Wittig reaction of 3. A reaction mechanism of the molecular rearrangement of substances (3) is proposed.

  DOI：

  10.3987/com-98-8305

文献信息

• Synthesis of 3-thiocyanato-1<i>H</i>,3<i>H</i>-quinoline-2,4-diones
  作者：Antonín Klásek、Jirí Polis、Vladimír Mrkvička、Janez Košmrlj

  DOI：10.1002/jhet.5570390632

  日期：2002.11

  4-Hydroxy-1H-quinolin-2-ones (1) react with thiocyanogen in acetic acid to the corresponding 3-thiocyanato-1H,3H-quinoline-2,4-diones (2) in good yields. In some cases, 3-bromo-1H,3H-quinoline-2,4-diones (4) were isolated as minor reaction products. Compounds 2 are very reactive towards nucleophiles and easily hydrolyze to the corresponding 4-hydroxy-1H-quinoline-2-ones (1).

  4-Hydroxy-1 H -quinolin-2-ones（1）在乙酸中与硫氰酸根反应生成相应的3-thiocyanato-1 H，3 H -quinoline-2,4-diones（2），产率高。在某些情况下，3-溴1 H，3 H-喹啉-2,4-二酮（4）被分离为次要反应产物。化合物2对亲核试剂具有很高的反应性，并容易水解为相应的4-羟基-1 H-喹啉-2-酮（1）。