methyl 3-(1-pyrrolidyl)propionate | 99233-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 3-(1-pyrrolidyl)propionate
• 英文别名: 3-pyrrol-1-yl-propionic acid methyl ester；3-Pyrrol-1-yl-propionsaeure-methylester；Methyl 3-(1H-pyrrol-1-yl)propanoate；methyl 3-pyrrol-1-ylpropanoate
• CAS: 99233-38-2
• 化学式: C₈H₁₁NO₂
• mdl: MFCD14586856
• 分子量: 153.181
• InChiKey: PMQPGLUUFXDPFM-UHFFFAOYSA-N

物化性质

• 沸点：
  232.2±23.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 3-(1-pyrrolidyl)propionate 在 lithium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 吡咯-1-丙酸
  参考文献：
  名称：

  Acyl radical cyclisation onto pyrroles

  摘要：

  Synthetically useful [1,2-a]-fused pyrroles, e.g. 2,3-dihydro-1H-pyrrolizidines substituted in the 1- and 7-positions, have been generated by acyl radical cyclisation onto pyrroles using N-(omega -acyl)-radicals generated front acyl-selenide precursors. The protocol does not require high pressures of CO. Mechanistic studies indicate the key role of azo radical initiators as oxidants of the intermediate pi -radicals. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01639-2
• 作为产物：
  描述：

  吡咯-1-丙酸 在 重氮甲烷 作用下， 生成 methyl 3-(1-pyrrolidyl)propionate
  参考文献：
  名称：

  Carol; Calvet, Anales de la Real Sociedad Espanola de Fisica y Quimica, 1958, vol. 54, p. 349,351

  摘要：

  DOI：

文献信息

• Organic Reactions in Ionic Liquids: A Simple and Highly Regioselective N-Substitution of Pyrrole
  作者：Zhen-Chu Chen、Zhang-Gao Le、Yi Hu、Qin-Guo Zheng

  DOI：10.1055/s-2004-829182

  日期：——

  In ionic liquids [Bmim][PF6] or [Bmim][BF4], pyrrole replaced the halogen atom of an alkyl halide to give the corresponding N-substituted pyrrole in excellent yield. Benzenesulfonyl chloride, p-methylbenzenesulfonyl chloride and benzoyl chloride reacted similarly with pyrroles to afford the N-substituted pyrroles in quantitative yield. Michael addition reaction of pyrrole with electrophilic olefins

  在离子液体 [Bmim][PF6] 或 [Bmim][BF4] 中，吡咯取代了卤代烷的卤素原子，以优异的收率得到相应的 N-取代吡咯。苯磺酰氯、对甲基苯磺酰氯和苯甲酰氯与吡咯类似地反应，以定量产率提供N-取代吡咯。吡咯与亲电烯烃的迈克尔加成反应以高度区域选择性的方式完成，得到 N-烷基吡咯。
• A new and high yielding synthesis of unstable pyrroles via a modified Clauson-Kaas reaction
  作者：Brendon S. Gourlay、Peter P. Molesworth、John H. Ryan、Jason A. Smith

  DOI：10.1016/j.tetlet.2005.11.104

  日期：2006.1

  An investigation of the reaction requirements to effect the Clauson-Kaas pyrrole synthesis led to the formulation of a new procedure that avoids the contact of pyrroles to heat or strongly acidic conditions that cause decomposition of the desired products. The procedure involves mild hydrolysis of 2,5-dimethoxytetrahydrofuran in water to the activated species 2,5-dihydroxytetrahydrofuran that reacts

  对影响克劳森-卡斯（Clauston-Kaas）吡咯合成的反应要求的研究导致制定了一种新的方法，该方法避免了吡咯与热或强酸性条件接触，从而避免了所需产物的分解。该方法包括将2,5-二甲氧基四氢呋喃在水中温和水解为活化的物质2,5-二羟基四氢呋喃，使其在室温下与乙酸酯缓冲液中的伯胺反应，以高收率得到N-取代的吡咯。在手性胺的情况下，吡咯的形成在没有可检测的差向异构的情况下进行。还可以高收率和高纯度获得对酸或热敏感的吡咯。
• Short, enantiogenic syntheses of (-)-indolizidine 167B and (+)-monomorine
  作者：Charles W. Jefford、Qian Tang、Alexander Zaslona

  DOI：10.1021/ja00009a043

  日期：1991.4

  The enantiogenic syntheses of (−)-indolizidine 167B (1) and (+)-monomorine (2) are described. D-Norvaline and L-alanine are converted into their 1-pyrrole derivatives by reaction with 2,5-dimethoxytetrahydrofuran. Thereafter, Arndt-Eistert homologation of the N-alkanoic acid substituent, followed by rhodium (II) acetate catalyzed decomposition of its α-diazo ketone derivative, provides the relevant

  描述了 (-)-indolizidine 167B (1) 和 (+)-monomorine (2) 的对映体合成。D-正缬氨酸和 L-丙氨酸通过与 2,5-二甲氧基四氢呋喃反应转化为它们的 1-吡咯衍生物。此后，N-链烷酸取代基的 Arndt-Eistert 同系化，然后乙酸铑 (II) 催化分解其 α-重氮酮衍生物，提供相关的双环前体，其既得手性指导催化氢化，得到 1 和 2。 2 中的 5-丁基侧链是通过从丁酰氯和 L-丙氨酸的吡咯类似物获得的混合酸酐的先前路易斯酸催化重排而制备的
• JEFFORD, CHARLES W.;TANG, QIAN;ZASLONA, ALEXANDER, J. AMER. CHEM. SOC., 113,(1991) N, C. 3513-3518
  作者：JEFFORD, CHARLES W.、TANG, QIAN、ZASLONA, ALEXANDER

  DOI：——

  日期：——
• Pentoses and Hexoses as Sources of New Melanoidin-like Maillard Polymers
  作者：Roland Tressl、Georg T. Wondrak、Leif-A. Garbe、Ralph-Peter Krüger、Dieter Rewicki

  DOI：10.1021/jf970973r

  日期：1998.5.1

  N-Substituted pyrroles (1), 2-furaldehyde (2), and N-substituted 2-formylpyrroles (3), formed in pentose (hexose) Maillard systems, were identified as components of extraordinary polycondensation activity. The polycondensation was studied in model experiments with N-methylpyrrole (1a)/N-methyl-2-formylpyrrole (3a), N-(2-methoxycarbonylethyl)pyrrole (1b)/N-(2-methoxycarbonylethyl)-2-formylpyrrole (3b), N-methyl-2-formylpyrrole (3a), N-methylpyrrole (1a)/2-furaldehyde (2), and N-(2-methoxycarbonylethyl)pyrrole (1b)/2-furaldehyde (2), respectively. MALDI-TOF-MS spectra indicated regular oligomers of up to 15-30 methine-bridged N-methyl(or N-2-methoxycarbonylethyl)-pyrroles. With participation of aldehyde 2, furan rings instead of pyrrole rings were incorporated. The oligomers 5-11 were isolated and identified by MS and NMR techniques. A complementary experiment with N-methyl-2-[C-13]formylpyrrole ([(CHO)-C-13]-3a)/N-methylpyrrole (1a) was performed. The relevance of the new (type II) melanoidin-like oligomers/polymers in Maillard reactions is discussed and, in conclusion, a corresponding structure for native melanoidins is proposed. The oligomers 5, 6, 8, and 9 were tested for antioxidative activity in an iron(III) thiocyanate assay.