N-苯基吡咯烷-1-甲酰胺 | 5626-53-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-苯基吡咯烷-1-甲酰胺
• 英文名称: pyrrolidine-1-carboxylic acid phenylamide
• 英文别名: N-phenylpyrrolidine-1-carboxamide；N-phenyl-(1-pyrrolidine)carboxamide
• CAS: 5626-53-9
• 化学式: C₁₁H₁₄N₂O
• mdl: MFCD00594244
• 分子量: 190.245
• InChiKey: NTBKXPQLQPBJJL-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  387.0±15.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  N-苯基吡咯烷-1-甲酰胺 在 正丁基锂 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 乙腈 为溶剂， 反应 26.0h， 生成 N-(diazoacetoacetyl)-N-phenyl-1-pyrrolidinecarboxamide
  参考文献：
  名称：

  Synthesis of nitrogen-containing polycycles via rhodium(II)-induced cyclization-cycloaddition and insertion reactions of N-(diazoacetoacetyl)amides. Conformational control of reaction selectivity

  摘要：

  A series of diazoacetoacetamides, when treated with a catalytic quantity of a rhodium(II) carboxylate, were found to afford products derived from both a carbonyl ylide intermediate and intramolecular C-H insertion. With 3-(N-(diazoacetoacetyl)amino)propanoate derivatives, the rhodium(II)-catalyzed carbenoid reactions exhibit a strong preference for formation of a beta-lactam ring. This is attributed to a conformational preference that juxtaposes the carbenoid center and the less sterically encumbered amide substituent and is consistent with an activating influence on the C-H bond adjacent to the amide nitrogen atom. Carbonyl ylide products derived from carbenoid cyclization onto the ester carbonyl group are also formed, and their relative yields are dependent on electronic influences from the bridging ligands of rhodium(II). Treatment of a series of cyclic diazoimides with rhodium(II) acetate resulted in cyclization of the rhodium carbenoid onto the adjacent imide carbonyl group to produce an isomunchnone dipole. Cyclization onto the imide carbonyl group occurs exclusively even when C-H insertion or aromatic substitution reactions of the carbenoid intermediate are favorable, and this selectivity is also attributed to conformational preferences that juxtapose the carbenoid center and imide carbonyl group. The isomunchnone dipole readily undergoes cycloaddition with several different dipolarophiles to give 1,3-dipolar cycloadducts. When acetylenic dipolarophiles were used as the trapping agents, the initial cycloadducts were found to undergo a [4 + 2]-cycloreversion, producing substituted furans in high yield. The generality of the method was demonstrated by varying the ring size of the cyclic imide. An analogous cyclization-cycloaddition reaction also occurred using diazoacetoacetyl-substituted ureas.

  DOI：

  10.1021/jo00002a058
• 作为产物：
  描述：

  N-苯基甲酰胺 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.03h， 生成 N-苯基吡咯烷-1-甲酰胺
  参考文献：
  名称：

  Synthesis of unsymmetrical phenylurea derivatives via oxidative cross coupling of aryl formamides with amines under metal-free conditions

  摘要：

  通过使用高价碘试剂作为外部氧化剂，在良好的产率下，将N-芳基甲酰胺直接转化为相应的苯基脲衍生物，通过形成异氰酸酯中间体实现。

  DOI：

  10.1039/c4nj01668h

文献信息

• Synthesis of Unsymmetrical Ureas by Sulfur-Assisted Carbonylation with Carbon Monoxide and Oxidation with Molecular Oxygen under Mild Conditions­
  作者：Takumi Mizuno、Takeo Nakai、Masatoshi Mihara

  DOI：10.1055/s-0029-1216863

  日期：2009.8

  pressure of carbon monoxide and oxygen at room temperature, N,N-dialkyl-N′-arylureas were selectively accessible from secondary amines, aromatic amines, and sulfur in good to excellent yields. For example, N-butyl-N-methyl-N′-(3,4-dichlorophenyl)urea, which is used as a herbicide (neburon), was afforded successfully from butylmethylamine (2 equiv), 3,4-dichloroaniline (1 equiv) and sulfur (1 equiv) in

  在室温下一氧化碳和氧气的环境压力下，N，N-二烷基-N'-芳基脲可以良好或极好的收率选择性地从仲胺，芳族胺和硫中获得。例如，成功地从丁基甲胺（2当量），3,4-二氯苯胺（1）获得了用作除草剂（尼布隆）的N-丁基-N-甲基-N '-（3,4-二氯苯基）脲。当在20°C的DMF中使用一氧化碳（0.1 MPa）和氧气（0.1 MPa）时，产率为79％（21.8 g），硫（1当量）。 不对称脲-一氧化碳-氧-硫-除草剂
• [EN] DIRECTED CONJUGATION TECHNOLOGIES<br/>[FR] TECHNOLOGIES DE CONJUGAISON DIRIGÉE
  申请人：KLEO PHARMACEUTICALS INC

  公开号：WO2021102052A1

  公开（公告）日：2021-05-27

  Among other things, the present disclosure provides technologies for site-directed conjugation of various moieties of interest to target agents. In some embodiments, the present disclosure utilizes target binding moieties to provide high conjugation efficiency and selectivity. In some embodiments, provided technologies are useful for preparing antibody conjugates.

  本公开提供了用于将各种感兴趣的分子与目标剂进行定点偶联的技术。在某些实施方式中，本公开利用目标结合分子以提供高偶联效率和选择性。在某些实施方式中，所提供的技术可用于制备抗体偶联物。
• Highly Efficient Synthesis of Ureas and Carbamates from Amides by Iodosylbenzene-Induced Hofmann Rearrangement
  作者：Peng Liu、Zhiming Wang、Xianming Hu

  DOI：10.1002/ejoc.201101784

  日期：2012.4

  A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. Symmetric and asymmetric ureas and carbamates can be prepared by this procedure in up to 98 % yield. Ureidopeptides can also be prepared in good yield by this method.

  描述了一种使用碘代苯作为氧化剂从酰胺合成 1,3-二取代脲和氨基甲酸酯的简单有效的方法。对称和不对称尿素和氨基甲酸酯可以通过该程序以高达 98% 的产率制备。通过该方法也可以以良好的产率制备脲肽。
• Accelerating effects of <i>N</i> -aryl-<i>N</i> ′,<i>N</i> ′-dialkyl ureas on epoxy-dicyandiamide curing system
  作者：Xiang Dong Liu、Mika Kimura、Atsushi Sudo、Takeshi Endo

  DOI：10.1002/pola.24329

  日期：2010.12.1

  This report focuses on epoxy‐dicyandiamide (DICY) curing system accelerated by N‐aryl‐N′,N′‐dialkyl urea, aiming at clarifying the accelerating mechanism and the relationship between accelerating effect and molecular structure of the accelerators. Nine N‐aryl‐N′,N′‐dialkyl ureas were synthesized and investigated with measurements of differential scanning calorimetry, thermo gravimetric/differential

  本报告重点介绍了由N-芳基-N '，N'-二烷基脲促进的环氧-双氰胺（DICY）固化体系，旨在阐明促进机理以及促进效果与促进剂分子结构之间的关系。九个N-芳基-N '，N合成了``-二烷基脲''，并通过差示扫描量热法，热重/差热分析和NMR光谱进行了研究。结果表明，脲在环氧化物的存在下通过热解离而释放出相应的仲胺，这导致了叔胺的形成，从而催化了DICY与环氧化物的加成反应。此外，发现了能够释放更多的致密胺的尿素表现出更高的促进效果的趋势。©2010 Wiley Periodicals，Inc. J Polym Sci A部分：Polym Chem，2010年
• Hydroamination of carbodiimides, isocyanates, and isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(<scp>iv</scp>) complex
  作者：Jayeeta Bhattacharjee、Suman Das、Ravi K. Kottalanka、Tarun K. Panda

  DOI：10.1039/c6dt03063g

  日期：——

  isothiocyanates by a bis(phosphinoselenoic amide) supported titanium(IV) complex as a precatalyst is reported here. The titanium(IV) complex [Ph2P(Se)NCH2CH2NPPh2(Se)}Ti(NMe2)2] (1) was synthesised by the reaction of tetrakis-(dimethylamido)titanium(IV) [Ti(NMe2)4] with [Ph2P(Se)NHCH2CH2NHPPh2(Se)}] in toluene at ambient temperature. Titanium complex 1 proved to be a competent pre-catalyst for the addition of

  此处报道了由双（膦亚硒酸酰胺）负载的钛（IV）配合物作为预催化剂对诸如碳二亚胺，异氰酸酯和异硫氰酸酯之类的杂枯烯的加氢胺化反应。通过四-（二甲基氨基）钛（IV）的反应合成了钛（IV）络合物[Ph 2 P（Se）NCH 2 CH 2 NPPh 2（Se）} Ti（NMe 2）2 ]（1）[ Ti（NMe 2）4 ]和[Ph 2 P（Se）NHCH 2 CH 2 NHPPh 2（Se）}]在室温下于甲苯中。钛配合物1被证明是在碳二亚胺，异氰酸酯和异硫氰酸酯上加成胺N–H键的有效预催化剂。反应范围扩大到脂肪族和芳香族胺与苯基异氰酸酯和苯基异硫氰酸酯在甲苯溶剂中的反应，在室温下以5摩尔％的催化剂负载量快速进行，从而生成相应的尿素和硫脲衍生物，最高可达99％。然而，环境温度对于1，3-二环己基碳二亚胺的氢化胺化是必需的。与异氰酸酯的胺加成反应显示出相对于催化剂1的一级动力学以及基材。通过分离作为

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