3-氧代-3-(吡咯烷-1-基)丙酸甲酯 | 76311-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 3-氧代-3-(吡咯烷-1-基)丙酸甲酯
• 英文名称: methyl 3-oxo-3-pyrrolidin-1-yl-propionate
• 英文别名: N-(carbomethoxymethyl)pyrrolidine；3-oxo-3-(pyrrolidin-1-yl)propionic acid methyl ester；methyl 3-oxo-3-pyrrolidin-1-yl-propanoate；methyl 3-(pyrrolidin-1-yl)-3-oxopropanoate；methyl 3-oxo-3-pyrrolidin-1-ylpropanoate
• CAS: 76311-92-7
• 化学式: C₈H₁₃NO₃
• 分子量: 171.196
• InChiKey: GAMWBIRNDXNLPK-UHFFFAOYSA-N

物化性质

• 沸点：
  110-113 °C(Press: 0.2 Torr)
• 密度：
  1.160±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-氧代-3-(吡咯烷-1-基)丙酸甲酯 在 氢气 作用下， 以 乙二醇二甲醚 为溶剂， 160.0 ℃ 、3.0 MPa 条件下， 反应 40.0h， 生成 N-正丙基吡咯烷
  参考文献：
  名称：

  在温和条件下将酰胺催化加氢为胺

  摘要：

  在（不是很大）压力下：已开发出一种使用双金属Pd-Re催化剂将叔酰胺和仲酰胺氢化成胺的通用方法，具有优异的选择性。反应在低压和较低温度下进行。该方法为有机化学家提供了一种简单可靠的胺合成工具。

  DOI：

  10.1002/anie.201207803
• 作为产物：
  描述：

  methyl 7-azido-3-oxoheptanoate 在 三氟乙酸 作用下， 以69%的产率得到3-氧代-3-(吡咯烷-1-基)丙酸甲酯
  参考文献：
  名称：

  Intramolecular Schmidt Reactions of Alkyl Azides with Ketones: Scope and Stereochemical Studies

  摘要：

  The intramolecular Schmidt reaction of alkyl azides and ketones has been demonstrated. The reaction is proposed to occur via initial attack of an azide on a ketone activated by a variety of protic or Lewis acids, including trifluoroacetic acid, titanium tetrachloride, and others. The resulting azidohydrin undergoes a direct rearrangement to afford the product amide and molecular nitrogen. When cyclic ketones are used, fused bicyclic lactams of types encountered in a wide variety of natural products are obtained. Although the distance allowed between the carbonyl group and the alkyl azide is quite restricted, the reaction is general with respect to the ketone component, including acyclic ketones and cyclic substrates ranging from standard to large ring sizes. The reaction also succeeds with aldehydes, although elimination or hydride migration products compete. In several cases examined, the reaction was found to proceed with retention of configuration at the migrating carbon. Competing reactions with beta-diketones and alpha,beta-unsaturated ketones were found to predominate over ring expansion.

  DOI：

  10.1021/ja00147a006

文献信息

• NOVEL USES OF ESTERAMIDE COMPOUNDS
  申请人：Guglieri Massimo

  公开号：US20130210933A1

  公开（公告）日：2013-08-15

  The use of an esteramide compound, alone or as a mixture of the following formula (I): R 1 OOC-A-CONR 2 R 3 (I) is described, wherein: A is a covalent bond or a methylene group —CH 2 —, R 1 is an optionally substituted hydrocarbon group having from 1 to 36 carbon atoms, R 2 and R 3 , either identical or different, are groups selected from a hydrogen atom and optionally substituted hydrocarbon groups comprising from 1 to 36 carbon atoms, R 2 and R 3 may form together a ring having the nitrogen atom to which they are bound, said ring being, if need be, substituted and/or having an additional heteroatom and R 2 and R 3 not being simultaneously hydrogens. Also described, are applications for using the esteramide compound as a solvent, a co-solvent, a coalescence agent, a crystallization inhibitor, a plasticizer or an agent for increasing biological activity.

  该专利描述了一种酯酰胺化合物的使用，可以单独使用，也可以作为以下式（I）的混合物： R1OOC-A-CONR2R3（I） 其中： A是一个共价键或一个亚甲基基团-CH2-， R1是一个可选择取代的碳原子数为1到36的碳氢基团， R2和R3，可以相同也可以不同，是从氢原子和可选择取代的碳原子数为1到36的碳氢基团中选择的基团， R2和R3可以一起形成一个含有它们结合的氮原子的环，该环如有必要，可以被取代和/或具有额外的杂原子， R2和R3不能同时是氢原子。 此外，还描述了将该酯酰胺化合物用作溶剂、共溶剂、凝聚剂、结晶抑制剂、增加生物活性的塑化剂或剂。
• Synthesis of Some 4-Oxothiochromenes and Related Compounds
  作者：Andris J. Liepa、Oanh Nguyen、Simon Saubern

  DOI：10.1071/ch05205

  日期：——

  Thiosalicylic acids react with 2-substituted N,N-dialkyl acetamides to give 3-substituted-N,N-dialkyl-2-amino-4-oxothiochromenes 13. N-Alkyl 2-piperidone and analogous caprolactams give derivatives of 1,2,3,4-tetrahydrothiochromeno[2,3-b]pyridin-5-one 16a–16d and 7,8,9,10-tetrahydro-6H-5-thia-6-aza-cyclohepta-[b]naphthalen-11-one 16e, 16f. 2-Mercaptonicotinic acid gave a 1,2,3,4-tetrahydro-9-thia-1

  硫代水杨酸与 2-取代的 N,N-二烷基乙酰胺反应生成 3-取代的-N,N-二烷基-2-氨基-4-氧代噻吩 13。N-烷基 2-哌啶酮和类似的己内酰胺生成 1,2 的衍生物， 3,4-tetrahydrothiochromeno[2,3-b]pyridin-5-one 16a-16d 和 7,8,9,10-tetrahydro-6H-5-thia-6-aza-cyclohepta-[b]naphthalen-11-一个 16e、16f。2-Mercaptonicotinic acid 得到 1,2,3,4-tetrahydro-9-thia-1,8-diazaanthracen-10-one 16g 和 1,2,3,4-tetrahydro-9-thia-1,8-二氮杂蒽-10-硫酮 16h。
• REACTION OF α-BROMO-α,β-UNSATURATED ESTERS AND BUTENOLIDES WITH MALONAMIC ESTERS
  作者：Hisashi Takei、Yoshimasa Fukuda、Kazuhiro Sugaya、Takeo Taguchi、Tatsuo Kawara

  DOI：10.1246/cl.1980.1307

  日期：1980.10.5

  α-Bromo-α,β-unsaturated esters and α-bromobutenolides reacted with sodium salts of methyl malonamates to afford cyclopropanes, α-methoxycarbonyllactams and 5-amino-4-methoxycarbonyl-2,3-dihydrofurans. The last compounds could be easily converted into α-methoxycarbonyl-γ-lactones. The ratio of these compounds formed is influenced by the structures of both malonamates and unsaturated compounds, especially

  α-溴-α,β-不饱和酯和 α-溴丁烯内酯与丙二酸甲酯的钠盐反应生成环丙烷、α-甲氧基羰基内酰胺和 5-氨基-4-甲氧基羰基-2,3-二氢呋喃。最后的化合物可以很容易地转化为 α-甲氧基羰基-γ-内酯。形成的这些化合物的比例受丙二酸酯和不饱和化合物的结构影响，特别是受丙二酸酯氮原子上的取代基和反应条件的影响。
• Ir-catalyzed chemoselective reduction of β-amido esters: A versatile approach to β-enamino esters
  作者：Zhi-Ping Yang、Guang-Sheng Lu、Jian-Liang Ye、Pei-Qiang Huang

  DOI：10.1016/j.tet.2018.12.024

  日期：2019.3

  The conversion of β-amido esters to β-enamino esters is an indispensable step for some synthetic approaches to alkaloids and related medicines. Known methods for such transformation are not only stepwise, but also proceed with low atom-efficiency. Herein, we report a direct and versatile approach that features the Ir-catalyzed chemoselective reduction of β-amido esters with 1,1,3,3-tetramethyldisiloxane

  对于某些生物碱和相关药物的合成方法，β-酰胺基酯向β-烯氨基酯的转化是必不可少的步骤。用于这种转化的已知方法不仅是逐步的，而且以低原子效率进行。本文中，我们报道了一种直接且通用的方法，其特征在于用1,1,3,3-四甲基二硅氧烷（TMDS）进行Ir催化的β-酰胺基酯的化学选择性还原。另外，在某些脂环族β-烯胺酯的13 C NMR光谱中观察到缺少某些信号。这揭示了文献中长期存在但被忽略的现象。
• Design, synthesis, biological evaluation and molecular modelling studies of novel quinoline derivatives against Mycobacterium tuberculosis
  作者：Ram Shankar Upadhayaya、Jaya Kishore Vandavasi、Nageswara Rao Vasireddy、Vivek Sharma、Shailesh S. Dixit、Jyoti Chattopadhyaya

  DOI：10.1016/j.bmc.2009.02.026

  日期：2009.4

  our molecular modelling and docking studies on well-known diarylquinoline antitubercular drug R207910, the presence of phenyl, naphthyl and halogen moieties seem critical. Comparison of docking studies on different stereoisomers of R207910 as well as compounds from our data set, suggests importance of electrostatic interactions. Further structural analysis of docking studies on our compounds suggests

  我们在此描述了一系列的27种3-苄基-6-溴-2-溴-2-甲氧基-喹啉和2-[（6-溴-2-甲氧基-喹啉-3-基）酰胺的衍生物的合成和抗分枝杆菌活性。 -苯基-甲基]-丙二酸单甲酯。在Bactec分析的第1天，在固定浓度（6.25μg/ mL）的情况下，连续9天在体外评估了这些化合物的抗结核分枝杆菌H37Rv的抗分枝杆菌活性，并将其与未经处理的TB细胞培养物以及经异烟肼处理的对应物进行了比较，在相同的实验条件下 化合物3，8，17和18已显示出分枝杆菌活性的92–100％生长抑制，最小抑制浓度（MIC）为6.25μg/ mL。根据我们对著名的二芳基喹啉抗结核药物R207910的分子建模和对接研究，苯基，萘基和卤素部分的存在似乎至关重要。比较R207910的不同立体异构体以及我们数据集中的化合物的对接研究，表明静电相互作用的重要性。对我们化合物的对接研究的进一步结构分析表明，寻找具有潜在改进潜力的新的先导化合物是有吸引力的起点。