diethyl 2-(1-methyl-2-oxoindolin-3-yl)malonate | 811418-56-1

• 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: diethyl 2-(1-methyl-2-oxoindolin-3-yl)malonate
• 英文别名: diethyl (1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)propanedioate；diethyl 2-(1-methyl-2-oxo-3H-indol-3-yl)propanedioate
• CAS: 811418-56-1
• 化学式: C₁₆H₁₉NO₅
• 分子量: 305.331
• InChiKey: IQAJHLXTBWRNMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-(1-methyl-2-oxoindolin-3-yl)malonate 以 水 、 二甲基亚砜 为溶剂， 反应 5.0h， 以74%的产率得到ethyl 2-(1-methyl-2-oxoindolin-3-yl)acetate
  参考文献：
  名称：

  A Lewis-Acid Catalyzed Synthesis of Substituted Oxindole Derivatives

  摘要：

  Lewis acid-catalyzed cyclization of various 2-(N-arylcarbamoyl)-methylenemalonates to give nitrogen-containing benzo-annelated heterocycles was investigated in terms of selectivity. Reaction of substrates with various alkyl groups on nitrogen proceeded to give oxindole derivatives. Cyclization reaction of diester-amides of MeO and halooen-substituted anilines in the presence of catalytic Lewis acid (ZnCl2, SnCl4, AlCl3, Zn(OTf)(2), Sc(OTf)(3), etc.) gave oxindoles in high yields. Interesting regioselectivity was observed for meta- halogen substrates. Dimethoxyisoquinoline analogs were also obtained by this reaction using a catalytic Lewis acid.

  DOI：

  10.3987/com-05-s(t)25
• 作为产物：
  描述：

  1,1-diethyl 2-hydrogen ethenetricarboxylate 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 diethyl 2-(1-methyl-2-oxoindolin-3-yl)malonate
  参考文献：
  名称：

  刘易斯酸促进乙烯三羧酸酯衍生物芳族化合物的环化。通过Friedel-Crafts分子内迈克尔加成反应，新型合成羟吲哚和苯并呋喃酮。

  摘要：

  在各种路易斯酸的存在下，乙烯三​​羧酸酯衍生物芳族化合物的新型环化反应可通过弗里德-克来福特分子内迈克尔加成反应以高收率得到苯并环化的环状化合物，例如羟吲哚和苯并呋喃衍生物。例如，在室温下在ZnCl 2存在下使2-[（（N-甲基-N-苯基氨基甲酰基）亚甲基]丙二酸二乙酯（1a）在室温下反应，得到2-（1-甲基-2-氧代吲哚-3-基）二乙基酯。丙二酸酯（2a），产率98％。反应还用催化量的路易斯酸例如AlCl 3，ZnCl 2，ZnBr 2，Sc（OTf）3或InBr 3进行。

  DOI：

  10.1039/b408728c

文献信息

• [3+2]-Annulation of oxindolinyl-malononitriles with Morita–Baylis–Hillman acetates of nitroalkenes for the regio- and diastereoselective synthesis of spirocyclopentane-indolinones
  作者：Abhishek Pareek、Sudheesh T. Sivanandan、Shweta Bhagat、Irishi N.N. Namboothiri

  DOI：10.1016/j.tet.2022.132650

  日期：2022.2

  highly regio- and stereoselective [3 + 2] annulation with 1,3-bielectrophilic nitroallylic acetates leading to spirocyclopentane-indolinones. The reaction takes place in the presence of DABCO in THF at room temperature and affords the multi-functional spirocyclic compounds possessing three chiral centers, including a spiro-chiral center in good to excellent yields and short reaction time. The key role

  3-Oxindolinyl-丙二腈作为 1,2-双亲核试剂参与高度区域和立体选择性的 [3 + 2] 环化反应，与 1,3-双亲电子硝基烯丙基乙酸酯形成螺环戊烷-吲哚啉酮。该反应在 THF 中的 DABCO 存在下于室温下进行，并提供具有三个手性中心（包括一个螺手性中心）的多功能螺环化合物，其产率良好至极好，反应时间短。丙二腈部分在控制反应性和选择性方面的关键作用也已得到证实。基于DFT计算结果，提出了用于[3 + 2]环化的S N 2'-分子内迈克尔加成途径。
• A Lewis-Acid Catalyzed Synthesis of Substituted Oxindole Derivatives
  作者：Shoko Yamazaki、Machiko Yamamoto、Satoshi Morikawa

  DOI：10.3987/com-05-s(t)25

  日期：——

  Lewis acid-catalyzed cyclization of various 2-(N-arylcarbamoyl)-methylenemalonates to give nitrogen-containing benzo-annelated heterocycles was investigated in terms of selectivity. Reaction of substrates with various alkyl groups on nitrogen proceeded to give oxindole derivatives. Cyclization reaction of diester-amides of MeO and halooen-substituted anilines in the presence of catalytic Lewis acid (ZnCl2, SnCl4, AlCl3, Zn(OTf)(2), Sc(OTf)(3), etc.) gave oxindoles in high yields. Interesting regioselectivity was observed for meta- halogen substrates. Dimethoxyisoquinoline analogs were also obtained by this reaction using a catalytic Lewis acid.
• A Lewis acid-promoted cyclization of ethenetricarboxylate derivative aromatic compounds. Novel syntheses of oxindoles and benzofuranones via Friedel–Crafts intramolecular Michael addition
  作者：Shoko Yamazaki、Satoshi Morikawa、Yuko Iwata、Machiko Yamamoto、Kaori Kuramoto

  DOI：10.1039/b408728c

  日期：——

  A novel cyclization reaction of ethenetricarboxylate derivative aromatic compounds in the presence of various Lewis acids gave benzo-annulated cyclic compounds such as oxindole and benzofuran derivatives via Friedel-Crafts intramolecular Michael addition in high yields. For example, the reaction of diethyl 2-[(N-methyl-N-phenylcarbamoyl)methylene]malonate (1a) in the presence of ZnCl2 at room temperature

  在各种路易斯酸的存在下，乙烯三​​羧酸酯衍生物芳族化合物的新型环化反应可通过弗里德-克来福特分子内迈克尔加成反应以高收率得到苯并环化的环状化合物，例如羟吲哚和苯并呋喃衍生物。例如，在室温下在ZnCl 2存在下使2-[（（N-甲基-N-苯基氨基甲酰基）亚甲基]丙二酸二乙酯（1a）在室温下反应，得到2-（1-甲基-2-氧代吲哚-3-基）二乙基酯。丙二酸酯（2a），产率98％。反应还用催化量的路易斯酸例如AlCl 3，ZnCl 2，ZnBr 2，Sc（OTf）3或InBr 3进行。