methyl 1-acetyl-2-oxindolin-3-ylideneacetate | 61936-92-3

• 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: methyl 1-acetyl-2-oxindolin-3-ylideneacetate
• 英文别名: methyl 1-acetyl-2-oxo-3(2H)-indolylideneacetate；(E)-methyl 2-(1-acetyl-2-oxoindolin-3-ylidene)acetate；((E)-1-acetyl-2-oxo-1,2-dihydro-indol-3-ylidene)-acetic acid methyl ester；Methyl 2-(1-acetyl-2-oxoindolin-3-ylidene)acetate；methyl (2E)-2-(1-acetyl-2-oxoindol-3-ylidene)acetate
• CAS: 61936-92-3
• 化学式: C₁₃H₁₁NO₄
• 分子量: 245.235
• InChiKey: ASWBFUSHNDQBPA-JXMROGBWSA-N

物化性质

• 沸点：
  422.5±45.0 °C(Predicted)
• 密度：
  1.405±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 1-acetyl-2-oxindolin-3-ylideneacetate 在 copper diacetate 、 三乙胺 作用下， 以 1,4-二氧六环 、 苯 为溶剂， 反应 2.0h， 生成 dimethyl 5-<(o-acetylamino)phenyl>-1-(p-chlorophenyl)pyrazole-3,4-dicarboxylate
  参考文献：
  名称：

  Coda, Andreina Corsico; Desimoni, Giovanni; Monaco, Hugo Luis, Gazzetta Chimica Italiana, 1989, vol. 119, # 1, p. 13 - 18

  摘要：

  DOI：
• 作为产物：
  描述：

  靛红 、 alkaline earth salt of/the/ methylsulfuric acid 以 溶剂黄146 为溶剂， 反应 11.0h， 生成 methyl 1-acetyl-2-oxindolin-3-ylideneacetate
  参考文献：
  名称：

  Intramolecular Reactions of Oxindolyl Diazo Ketones

  摘要：

  重氮酮是通过标准方法从氧杂吲哚亚基乙酸甲酯（2-氧代-3(2H)-吲哚亚基乙酸甲酯）和 1,3-丁二烯以及 1,3-环己二烯的 Diels-Alder 加合物中制备出来的。然而，在研究的每种情况下，重氮酮都会与邻近的苯环发生作用，从而生成一种去甲卡二烯。

  DOI：

  10.1055/s-1992-26101

文献信息

• Core Structure-Based Design of Organocatalytic [3+2]-Cycloaddition Reactions: Highly Efficient and Stereocontrolled Syntheses of 3,3′-Pyrrolidonyl Spirooxindoles
  作者：Bin Tan、Xiaofei Zeng、Wendy Wen Yi Leong、Zugui Shi、Carlos F. Barbas、Guofu Zhong

  DOI：10.1002/chem.201103449

  日期：2012.1.2

  Extraordinary levels of stereocontrol were achieved in an efficient organocatalytic asymmetric [3+2]‐cycloaddition reaction between an α‐isothiocyanato imide and various methyleneindolinones. Simple precursors were used for the rapid construction of spirocyclic oxindole derivatives with high enantiopurity and structural diversity, thus providing a new avenue of significance to medicinal chemistry and

  在α-异硫氰酸根酰亚胺和各种亚甲基吲哚满酮之间进行有效的有机催化不对称[3 + 2]-环加成反应时，可以达到非同寻常的立体控制水平。简单的前体被用于快速构建具有高对映体纯度和结构多样性的螺环羟吲哚衍生物，从而为药物化学和面向多样性的合成提供了重要的新途径。
• Heterodiene synthesis. Part XVII. Reactions of 2-oxoindolin-3-ylidene derivatives with enamines: a Michael pathway as an alternative to 1,2- and 1,4-cycloadditions
  作者：Gianfranco Tacconi、Anna Gamba Invernizzi、Giovanni Desimoni

  DOI：10.1039/p19760001872

  日期：——

  The reactions of enamines with 2-oxoindolin-3-ylidene-acetates and -acetophenones have been studied. With enamines derived from aldehydes the former gave either 1,2- or 1,4-cycloaddition products, as previously described for the latter. However, both substrates gave only Michael-type adducts with enamines derived from cyclopentanone. The mechanism is discussed in terms of both frontier orbital interaction

  已经研究了烯胺与2-氧吲哚-3-基-乙酸酯和-苯乙酮的反应。用衍生自醛的烯胺，前者得到1，2-或1，4-环加成产物，如前所述。但是，两种底物仅与衍生自环戊酮的烯胺一起给出了迈克尔型加合物。从边界轨道相互作用和稳定的偶极中间体的角度讨论了该机理。
• Reaction of 2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetic acid esters with benzene-1,2-diamine and 2-aminobenzenethiol
  作者：V. O. Koz’minykh、V. I. Goncharov、K. Sh. Lomidze、E. N. Koz’minykh

  DOI：10.1134/s1070428007010071

  日期：2007.1

  2-(2-Oxo-2,3-dihydro-1H-indol-3-ylidene)acetic acid esters reacted with benzene-1,2-diamine or 2-aminobenzenethiol to give (2-oxo-2,3-dihydro-1H-indol-3-yl)-substituted 3,4-dihydroquinoxalin-2(1H)-ones or 2H-1,4-benzothiazin-3(4H)-ones.
• Reaction of 2-(2-Oxo-1,2-dihydro-3H-indol-3-ylidene)acetic acids esters with phenylhydrazine
  作者：E. N. Koz’minykh、V. I. Goncharov、V. O. Koz’minykh、K. Sh. Lomidze、A. N. Berezin

  DOI：10.1134/s107042800710017x

  日期：2007.10

  2-(2-Oxo-1,2-dihydro-3H-indol-3-ylidene)acetic acids esters reacted with phenylhydrazine yielding products of the regioselective addition of the latter in the alpha-(C-2)-position of the exo ethylene bond, (2-oxo-2,3-dihydro-1H-indol-3-yl)(2-phenylhydrazino)acetic acids esters.
• CODA, ANDREINA CORSICO;DESIMONI, GIOVANNI;MONACO, HUGO LUIS;QUADRELLI, PA+, GAZZ. CHIM. ITAL., 119,(1989) N, C. 13-17
  作者：CODA, ANDREINA CORSICO、DESIMONI, GIOVANNI、MONACO, HUGO LUIS、QUADRELLI, PA+

  DOI：——

  日期：——

表征谱图