Bromo-acetic acid 3-benzyl-5-chloro-8-methyl-2,4-dioxo-1,2,3,4-tetrahydro-quinolin-3-yl ester | 220462-63-5

• 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: Bromo-acetic acid 3-benzyl-5-chloro-8-methyl-2,4-dioxo-1,2,3,4-tetrahydro-quinolin-3-yl ester
• CAS: 220462-63-5
• 化学式: C₁₉H₁₅BrClNO₄
• 分子量: 436.689
• InChiKey: OPJVJIJJXJMIAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  72.47
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Bromo-acetic acid 3-benzyl-5-chloro-8-methyl-2,4-dioxo-1,2,3,4-tetrahydro-quinolin-3-yl ester 在 sodium hydroxide 作用下， 以 氯仿 、 苯 为溶剂， 反应 6.17h， 生成 3a-benzyl-9-chloro-6-methyl-2,3a,4,5-tetrahydrofuro<2,3-c>quinoline-2,4-dione
  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 在 吡啶 、 过氧乙酸 、 sodium hydroxide 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 2.25h， 生成 Bromo-acetic acid 3-benzyl-5-chloro-8-methyl-2,4-dioxo-1,2,3,4-tetrahydro-quinolin-3-yl ester
  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

• Unprecedented Reactivity of 5-Substituted 3-Hydroxy-1,2,3,4-tetrahydroquinoline-2,4-diones with Ethyl (Triphenylphosphoranylidene)acetate
  作者：Antonín Klásek、Kamil Koristek、Jirí Polis Polis、Janez Kosmrlj

  DOI：10.3987/com-98-8305

  日期：——

  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.