1-(2-methylpropyl)-2,5-dimethylpyrrole | 21407-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(2-methylpropyl)-2,5-dimethylpyrrole
• 英文别名: 1-isobutyl-2,5-dimethyl-1H-pyrrole；2,5-dimethyl-1-(2-methylpropyl)-1H-pyrrole；2,5-dimethyl-1-(2-methylpropyl)pyrrole
• CAS: 21407-84-1
• 化学式: C₁₀H₁₇N
• mdl: MFCD12187091
• 分子量: 151.252
• InChiKey: IMOWSCLMRKEZJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  219.0±9.0 °C(Predicted)
• 密度：
  0.87±0.1 g/cm3(Predicted)
• LogP：
  3.540 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  异丁胺 、 2,5-己二酮 以 乙腈 为溶剂， 生成 1-(2-methylpropyl)-2,5-dimethylpyrrole
  参考文献：
  名称：

  中间体在Paal-Knorr合成吡咯。4-氧醛。

  摘要：

  研究了4-酮醛（例如4-氧己醛（4））与伯胺之间吡咯形成的机理。在有机溶剂4中容易形成分解为吡咯9的亚胺6。在磷酸盐缓冲液（pH 7.4）中，双氘（4-d2）和六氘（4-d6）类似物中的氘将反应速率降低了1.9倍和2.6，其远小于涉及碳氢键断裂的反应所表现出的同位素效应。此外，未环酮醛的氘标记物保持完整。这些结果表明，半胱氨酸5而不是烯胺8是经历环化的中间体。由于在羰基之一上不存在甲基取代基，因此4-氧代己醛的吡咯形成速率比2，5-己二酮大2个数量级。

  DOI：

  10.1021/tx00044a008

文献信息

• Efficient synthesis of substituted pyrroles through Pd(OCOCF3)2-catalyzed reaction of 5-hexen-2-one with primary amines
  作者：Xi Chen、Meng Yang、Min Zhou

  DOI：10.1016/j.tetlet.2016.10.029

  日期：2016.11

  An efficient and facile Pd(OCOCF3)2-catalyzed one-pot cascade protocol has been developed for the synthesis of multiple substituted pyrroles in good to excellent yields. Unlike the reported method starting from the 2-alkenal-1,3-carbonyl compounds, the process utilizes the less reactive 5-hexen-2-one and the method has great potential as a complement to the current developed methods.

  已经开发了一种有效且简便的Pd（OCOCF 3）2催化的一锅级联方案，用于合成多个取代的吡咯，产率高至优异。与报道的从2-链烯基-1,3-羰基化合物开始的方法不同，该方法利用了反应性较低的5-己烯-2-酮，该方法具有很大的潜力作为对当前开发方法的补充。
• Paal–Knorr Pyrrole Synthesis Using Recyclable Amberlite IR 120 Acidic Resin: A Green Approach
  作者：Aarti Devi、Shallu、M. L. Sharma、Jasvinder Singh

  DOI：10.1080/00397911.2010.540766

  日期：2012.5.15

  Abstract Amberlite IR 120 acidic resin, a polymer matrix, has been demonstrated as a catalyst for Paal-Knorr condensation of 2,5-hexadione with primary amines under solvent-free conditions. This is an efficient, mild, and green methodology for N-substituted pyrrole derivatives. GRAPHICAL ABSTRACT

  摘要 Amberlite IR 120 酸性树脂是一种聚合物基质，已被证明可作为 2,5-己二酮与伯胺在无溶剂条件下进行 Paal-Knorr 缩合的催化剂。这是一种用于 N 取代吡咯衍生物的高效、温和且绿色的方法。图形概要
• An h-1, c-13 and n-15 nmr study of the paal-knorr condensation of acetonylacetone with primary amines
  作者：Alan R. Katritzky、Taher I. Yousaf、Ban Chi Chen、Zeng Guang-Zhi

  DOI：10.1016/s0040-4020(01)87462-7

  日期：1986.1

  The reaction of primary amines with acetonylacetone is shown by H-1, C-13 and N-15 NMR spectroscopy to proceed to the -substituted -2, 5-dimethylpyrroles the intermediacy of -substituted imines. Increased steric hindrance reduces rates of imine formation and decay.

  H-1，C-13和N-15NMR光谱表明伯胺与丙酮基丙酮的反应进行到-取代的-2，5-二甲基吡咯的-取代的亚胺的中间体。空间位阻的增加会降低亚胺的形成和衰变速率。
• Novel 2,5-Hexanedione Analogues. Substituent-Induced Control of the Protein Cross-Linking Potential and Oxidation Susceptibility of the Resulting Primary Amine-Derived Pyrroles
  作者：Guozhang Xu、Malvinder P. Singh、Damodaragounder Gopal、Lawrence M. Sayre

  DOI：10.1021/tx000169q

  日期：2001.3.1

  The neurotoxic gamma -diketone, 2,5-hexanedione (2,5-HD), induces neurofilamentous swellings at prenodal sites in proximal axons as a consequence of pyrrolation of lysine E-amino groups on neurofilament proteins. However, there is disagreement as to whether pyrrole formation and the associated alteration of noncovalent interactions is sufficient to cause neurofilament accumulation, or whether pyrrole autoxidation and subsequent protein-protein cross-linking is an obligatory event. To investigate gamma -diketones that might form pyrroles inert to autoxidative-induced cross-linking, we synthesized 1,1,1-trifluoro-2,5-hexanedione, 3-(trifluoromethyl)-2,5-hexanedione (3-TFMHD), and two 3-(dialkylaminocarbonyl)-2,5-diketones and assessed their rates of pyrrole formation with amines, the oxidation susceptibility of the resulting pyrroles, and the protein cross-linking potential in vitro, relative to those of 3-methyl-2,5-hexanedione. 1,1,1-Trifluoro-2,5-hexanedione does not form pyrroles, but the three 2,5-HD analogues with an electron-withdrawing 3-substituent all rapidly formed pyrroles that were inert to autoxidation. Although 3-TMFHD nonetheless still induced cross-linking of ribonuclease A, by a nonoxidative mechanism independent of the pyrrole, the two 3-(dialkylaninocarbonyl)-2,5-diketones did not exhibit any protein cross-linking. As these two gamma -diketones possess aqueous-organic partitioning properties similar to those of 2,5-HD, they should serve as useful mechanistic probes in further studies.
• Layered zirconium phosphate and phosphonate as heterogeneous catalyst in the preparation of pyrroles
  作者：Massimo Curini、Francesca Montanari、Ornelio Rosati、Eduardo Lioy、Roberto Margarita

  DOI：10.1016/s0040-4039(03)00810-4

  日期：2003.5

  Pyrroles may be prepared by condensation of alkyl and aryl amines and 1,4-diketones (Paal-Knorr reaction) under potassium exchanged layered Zirconium phosphate and zirconium sulfophenyl phosphonate catalyst in solvent free conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.

表征谱图