3a-benzyl-9-chloro-6-methyl-2,3a,4,5-tetrahydrofuro<2,3-c>quinoline-2,4-dione | 220462-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 3a-benzyl-9-chloro-6-methyl-2,3a,4,5-tetrahydrofuro<2,3-c>quinoline-2,4-dione
• 英文别名: 3a-benzyl-9-chloro-6-methyl-5H-furo[2,3-c]quinoline-2,4-dione
• CAS: 220462-51-1
• 化学式: C₁₉H₁₄ClNO₃
• 分子量: 339.778
• InChiKey: RGPMZKKAPUCGSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3a-benzyl-9-chloro-6-methyl-2,3a,4,5-tetrahydrofuro<2,3-c>quinoline-2,4-dione 在 4-二甲氨基吡啶 、 环己基苯 作用下， 反应 0.67h， 以66%的产率得到1-benzyl-9-chloro-6-methyl-1,3,4,5-tetrahydrofuro<3,4-c>quinoline-3,4-dione
  参考文献：
  名称：

  呋喃[2,3- c ]喹啉-2,4（3a H，5 H）-二酮重排为呋喃[3,4- c ]喹啉-3,4（1 H，5 H）-二酮

  摘要：

  呋喃[2,3 - c ]喹啉-2,4（3a H，5 H）-二酮1的热辅助碱催化重排为相应的呋喃[3,4- c ]喹啉-3,4（1 H，报道了5 H）-二酮2，并提出了转化机理。

  DOI：

  10.1016/j.tetlet.2007.11.010
• 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 氯仿 、 溶剂黄146 、 苯 为溶剂， 反应 8.42h， 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

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.
• Rearrangement of furo[2,3-c]quinoline-2,4(3aH,5H)-diones to furo[3,4-c]quinoline-3,4(1H,5H)-diones
  作者：Stanislav Kafka、Janez Košmrlj、Antonín Klásek、Andrej Pevec

  DOI：10.1016/j.tetlet.2007.11.010

  日期：2008.1

  Thermally assisted base-catalyzed rearrangement of furo[2,3-c]quinoline-2,4(3aH,5H)-diones 1 to the corresponding furo[3,4-c]quinoline-3,4(1H,5H)-diones 2 is reported, and a mechanism of the transformation is proposed.

  呋喃[2,3 - c ]喹啉-2,4（3a H，5 H）-二酮1的热辅助碱催化重排为相应的呋喃[3,4- c ]喹啉-3,4（1 H，报道了5 H）-二酮2，并提出了转化机理。