methyl 4-(1H-indol-3-yl)-2-oxopyrrolidine-3-carboxylate | 92191-85-0

• 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 4-(1H-indol-3-yl)-2-oxopyrrolidine-3-carboxylate
• 英文别名: 4-(Indol-3-yl)-3-methoxycarbonyl-2-pyrrolidone
• CAS: 92191-85-0
• 化学式: C₁₄H₁₄N₂O₃
• 分子量: 258.277
• InChiKey: QTPWPZYBXKCFCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 4-(1H-indol-3-yl)-2-oxopyrrolidine-3-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.17h， 生成 4-(1H-吲哚-3-基)吡咯烷-2-酮
  参考文献：
  名称：

  Indole-containing derivatives of α-pyrrolidone: Synthesis and structure

  摘要：

  4-(Indol-3-yl)-2-pyrrolidone and its derivatives have been synthesized via sequential hydrogenation of indole-containing esters of 4-nitrobutanoic acid, alkaline hydrolysis of the resulting 3-methoxycarbonyl-2- pyrrolidones, and decarboxylation of the isolated 2-pyrrolidone-3-carboxylic acids. Structures of the products have been confirmed by IR, H-1 NMR, H-1-C-13 HMQC, and H-1-H-1 NOESY spectroscopy methods.

  DOI：

  10.1134/s1070363215080095
• 作为产物：
  描述：

  dimethyl 2-(1-(1H-indol-3-yl)-2-nitroethyl)malonate 在 sodium hypophosphite monohydrate 、 5%-palladium/activated carbon 、 亚膦酸 作用下， 以 2-甲基四氢呋喃 、 水 为溶剂， 反应 7.0h， 以78%的产率得到methyl 4-(1H-indol-3-yl)-2-oxopyrrolidine-3-carboxylate
  参考文献：
  名称：

  Reduction of aromatic and aliphatic nitro groups to anilines and amines with hypophosphites associated with Pd/C

  摘要：

  芳香和脂肪族硝基化合物在较短的反应时间内，以良好的收率和选择性还原为苯胺和胺。在多相催化剂2.5 mol%的Pd/C（5%）存在下，使用次磷酸钠和膦酸的混合物在两相水/2-甲基四氢呋喃体系中进行还原。

  DOI：

  10.1039/c3gc37024k

文献信息

• Reduction of aromatic and aliphatic nitro groups to anilines and amines with hypophosphites associated with Pd/C
  作者：Marc Baron、Estelle Métay、Marc Lemaire、Florence Popowycz

  DOI：10.1039/c3gc37024k

  日期：——

  The reduction of aromatic and aliphatic nitro groups to anilines and amines is performed with good yield and selectivity in short reaction times. A mixture of sodium hypophosphite and phosphinic acid is used in the presence of a heterogeneous catalyst 2.5 mol% of Pd/C (5%) in a biphasic water/2-MeTHF system.

  芳香和脂肪族硝基化合物在较短的反应时间内，以良好的收率和选择性还原为苯胺和胺。在多相催化剂2.5 mol%的Pd/C（5%）存在下，使用次磷酸钠和膦酸的混合物在两相水/2-甲基四氢呋喃体系中进行还原。
• Hydrazides of 4-aryl(hetaryl)-2-oxopyrrolidine-3-carboxylic acids: Synthesis and structure
  作者：N. V. Gorodnicheva、E. S. Ostroglyadov、O. S. Vasil’eva、V. V. Pelipko、V. V. Gurzhii、V. M. Berestovitskaya、E. S. Lipina

  DOI：10.1134/s1070428016110129

  日期：2016.11

  Proceeding from reactions of methyl 4-aryl(hetaryl)-2-oxopyrrolidine-3-caroxylates with hydrazine and phenylhydrazine a series of hydrazides of the corresponding 2-oxopyrrolidine-3-carboxylic acids was obtained combining in the molecule a lactam ring and carbohydrazide groups. Phenylhydrazides of 2-oxopyrrolidine-3-carboxylic acids possess the Z-configuration.

  从4-芳基（杂芳基）-2-氧吡咯烷-3-甲基丙烯酸甲酯与肼和苯肼的反应开始，得到一系列相应的2-氧吡咯烷-3-羧酸的酰肼，在分子中结合了内酰胺环和碳酰肼基团。 。2-氧吡咯烷-3-羧酸的苯酰肼具有Z-构型。
• Facile synthesis of heteroaryl substituted $\gamma$-lactams from nitrovinyl arenes
  作者：Seda ÇINAR、Canan ÜNALEROĞLU

  DOI：10.3906/kim-1705-25

  日期：——

  Aliphatic nitroalkanes with different functional groups were synthesized from the Michael addition reactions of active methylene compounds 2 and nitrovinyl arenes 1 in high yields. The synthesized Michael adducts were subjected to intramolecular cyclization to give heteroaryl substituted γ-lactams in good to high yields under mild reaction conditions.

  通过活泼的亚甲基化合物2与硝基乙烯芳烃1的迈克尔加成反应，合成了具有不同功能团的脂肪族硝基烷烃，产率较高。合成的迈克尔加成产物经受分子内环化反应，在温和反应条件下成功生成了杂芳基取代的γ-内酰胺，产率从良好到高。
• Indole-containing derivatives of α-pyrrolidone: Synthesis and structure
  作者：E. S. Ostroglyadov、O. S. Vasil’eva、S. M. Aleksandrova、V. V. Pelipko、V. M. Berestovitskaya、I. N. Tyurenkov、V. V. Bagmetova

  DOI：10.1134/s1070363215080095

  日期：2015.8

  4-(Indol-3-yl)-2-pyrrolidone and its derivatives have been synthesized via sequential hydrogenation of indole-containing esters of 4-nitrobutanoic acid, alkaline hydrolysis of the resulting 3-methoxycarbonyl-2- pyrrolidones, and decarboxylation of the isolated 2-pyrrolidone-3-carboxylic acids. Structures of the products have been confirmed by IR, H-1 NMR, H-1-C-13 HMQC, and H-1-H-1 NOESY spectroscopy methods.