4-chloro-1,3-dihydro-7-methyl-3-phenylacetoxy-2H-indol-2-one | 220462-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-chloro-1,3-dihydro-7-methyl-3-phenylacetoxy-2H-indol-2-one
• 英文别名: (4-Chloro-7-methyl-2-oxo-1,3-dihydroindol-3-yl) 2-phenylacetate
• CAS: 220462-47-5
• 化学式: C₁₇H₁₄ClNO₃
• 分子量: 315.756
• InChiKey: SBQWVARLJWSRNG-UHFFFAOYSA-N

物化性质

• 沸点：
  455.1±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  4-chloro-1,3-dihydro-7-methyl-3-phenylacetoxy-2H-indol-2-one 在 4-二甲氨基吡啶 作用下， 以 xylene 为溶剂， 生成 4-氯-7-甲基靛红
  参考文献：
  名称：

  新型3-Acyloxy-1,3-dihydro-2 H-吲哚-2-ones和Isomeric 4-Acyl-1,4-dihydro-3,1-benzoxazin-2-ones的合成：3-Hydroxyquinoline-的双重重排2.4（1 H，3 H）-二酮

  摘要：

  取代的3-羟基喹啉-2,4（1 H，3 H）-二酮3转化为3-酰氧基-1,3-二氢-2 H-吲哚-2-酮4和异构体4-酰基-1,4-二氢3，1-苯并恶嗪-2-酮5。研究了取代基和反应条件对反应过程的影响。在所提出的机制中，发生了双重重排。α酮醇重排的3，导致α羟基β二酮中间体8，之后是重排同分异构的α酮醇酯4和5。

  DOI：

  10.1016/s0040-4020(00)00057-0
• 作为产物：
  描述：

  3-benzyl-5-chloro-4-hydroxy-8-methyl-1H-quinolin-2-one 在 过氧乙酸 、 sodium hydroxide 、 溶剂黄146 作用下， 以 溶剂黄146 、 xylene 为溶剂， 反应 4.0h， 生成 4-chloro-1,3-dihydro-7-methyl-3-phenylacetoxy-2H-indol-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 Novel 3-Acyloxy-1,3-dihydro-2H-indol-2-ones and Isomeric 4-Acyl-1,4-dihydro-3,1-benzoxazin-2-ones: Double Rearrangement of 3-Hydroxyquinoline-2,4(1H,3H)-diones
  作者：Antonı́n Klásek、Kamil Kořistek、Jiřı́ Polis、Janez Košmrlj

  DOI：10.1016/s0040-4020(00)00057-0

  日期：2000.3

  3-dihydro-2H-indol-2-ones 4 and isomeric 4-acyl-1,4-dihydro-3,1-benzoxazin-2-ones 5. The influence of the substituents and the reaction conditions on the course of the reaction was studied. In the proposed mechanism a double rearrangement takes place; α-ketol rearrangement of 3, leading to α-hydroxy-β-diketone intermediate 8, is followed by a rearrangement to the isomeric α-ketol-esters 4 and 5.

  取代的3-羟基喹啉-2,4（1 H，3 H）-二酮3转化为3-酰氧基-1,3-二氢-2 H-吲哚-2-酮4和异构体4-酰基-1,4-二氢3，1-苯并恶嗪-2-酮5。研究了取代基和反应条件对反应过程的影响。在所提出的机制中，发生了双重重排。α酮醇重排的3，导致α羟基β二酮中间体8，之后是重排同分异构的α酮醇酯4和5。
• 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.