2-butyl-3-propylpyrrole | 63045-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-butyl-3-propylpyrrole
• 英文别名: 2-butyl-3-propyl-1H-pyrrole
• CAS: 63045-62-5
• 化学式: C₁₁H₁₉N
• 分子量: 165.279
• InChiKey: JLCGJMDSOFIRGD-UHFFFAOYSA-N

物化性质

• 沸点：
  244.2±9.0 °C(Predicted)
• 密度：
  0.903±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2-butyl-3-propylpyrrole 在 potassium hydroxide semihydrate 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 6.5h， 生成 2-[anilino(5-butyl-4-propyl-1H-pyrrol-2-yl)methylene]malononitrile
  参考文献：
  名称：

  通过3-亚氨基-3 H-吡咯烷嗪-2-甲腈合成功能化的2,2'-和2,3'-联吡咯

  摘要：

  通过容易获得的1-氨基-3-亚氨基-3 H合成4-氨基-3-氰基-2,2'-和5'-氨基-4'-氰基-2,3'-联吡咯的新策略已经开发了-吡咯烷嗪-2-腈。导致5'-氨基-4'-氰基-2,3'-联吡咯的重排涉及中间体氮丙啶的形成，该中间体进行另一侧的开环。

  DOI：

  10.1016/j.tetlet.2016.07.006
• 作为产物：
  描述：

  5-壬酮 在 ammonium hydroxide 、 盐酸羟胺 、 potassium hydroxide 作用下， 以 氘代二甲亚砜 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 2-butyl-3-propylpyrrole
  参考文献：
  名称：

  方便地从酮，羟胺和1,2-二氯乙烷一锅合成吡咯

  摘要：

  在KOH / DMSO系统中（120°C，2-4 h），可通过酮，盐酸羟胺和1,2-二氯乙烷的一锅法轻松合成2-和2,3-取代的吡咯。吡咯含量为11–85％。脂族，脂环族，芳族和杂芳族酮可耐受反应条件。

  DOI：

  10.1016/j.tet.2014.11.031

文献信息

• Reaction of 2-(2,2-dicyano-1-ethylsulfanylethenyl)pyrroles with aniline: a route to 1-anilino-3-iminopyrrolizine-2-carbonitriles and 2-(1-anilino-2,2-dicyanoethenyl)pyrroles
  作者：Olga V. Petrova、Elena F. Sagitova、Igor A. Ushakov、Lyubov N. Sobenina、Al'bina I. Mikhaleva、Boris A. Trofimov

  DOI：10.1080/17415993.2014.987277

  日期：2015.3.4

  2-(2,2-Dicyano-1-ethylsulfanylethenyl)pyrroles readily react (ethanol, reflux) with aniline at position 1 of the ethenyl moiety in the presence of triethylamine to eliminate ethanethiol affording 1-anilino-3-iminopyrrolizine-2-carbonitriles or 2-(1-anilino-2,2-dicyanoethenyl)pyrroles in good yields. GRAPHICAL ABSTRACT

  在三乙胺的存在下，2-(2,2-Dicyano-1-ethylsulfanylethenyl)pyrroles 容易与苯胺反应（乙醇，回流）以消除乙硫醇，得到 1-anilino-3-iminopyrrolizine-2-carbonitriles或 2-(1-苯胺基-2,2-二氰基乙烯基)吡咯，收率良好。图形概要
• Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles
  作者：Olga V. Petrova、Arsalan B. Budaev、Elena F. Sagitova、Igor A. Ushakov、Lyubov N. Sobenina、Andrey V. Ivanov、Boris A. Trofimov

  DOI：10.3390/molecules26061692

  日期：——

  An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed.

  一种高效的方法已经开发出来，通过易得的酰基乙炔吡咯与硝酸胍的环缩合反应，合成了具有药用前景的吡咯-氨基嘧啶组合物（收率高达91%）。该反应在KOH/DMSO体系中在加热条件下进行（110-115°C，4小时）。在2-苯甲酰基乙炔吡咯的情况下，观察到形成的吡咯-氨基嘧啶作为N-（吡咯环的NH部分）和C-（氨基嘧啶的CH）亲核试剂意外地加到三键上。
• Eco-friendly, in-water, and catalyst-free assembly of acylethenylpyrroloimidazoindoles from 3<i>H</i>-indoles and acylpyrrolylacetylenes
  作者：Ludmila A. Oparina、Kseniya V. Belyaeva、Nikita A. Kolyvanov、Igor A. Ushakov、Denis N. Tomilin、Lyubov N. Sobenina、Anton V. Kuzmin、Boris A. Trofimov

  DOI：10.1039/d3nj05049a

  日期：——

  presumably proceeds in a micellar-like microreactor self-assembled in a two-phase aqueous medium that secures favorable mutual orientation of the merging molecules, providing a facile [2+3] concerted cycloaddition to finally form fused polyheterocyclic systems. The performed DFT calculations are in agreement with such mechanistic considerations, particularly those underlying the crucial role of water in the

  在E-酰基乙烯基官能化的二氢吡咯并[1',2':3,4]咪唑并[1,2- a ]吲哚分子中，基本和生物学上重要的杂环结构（例如吡咯、吲哚和咪唑）的合并是使用容易获得的酰基吡咯乙炔作为附加结构单元，在商业 3 H-吲哚平台上在水中实现了这一目标。整体产率达到88%（100℃，8h），明显优于使用传统溶剂（MeCN、MeNO 2、DMSO和CF 3 CH 2 OH）产生的产率，其中反应以一定速率进行大约长 10 倍（96 小时），但目标产物的产率较低（不高于 80%）。该反应可能在两相水介质中自组装的胶束状微反应器中进行，确保合并分子有利的相互取向，提供容易的[2+3]协同环加成，最终形成稠合多杂环系统。所执行的 DFT 计算与此类机械考虑一致，特别是那些水在所研究的级联过程中的关键作用的考虑。
• New Prodigiosin Derivatives Obtained by Mutasynthesis in <i>Pseudomonas putida</i>
  作者：Andreas S. Klein、Andreas Domröse、Patrick Bongen、Hannah U. C. Brass、Thomas Classen、Anita Loeschcke、Thomas Drepper、Luca Laraia、Sonja Sievers、Karl-Erich Jaeger、Jörg Pietruszka

  DOI：10.1021/acssynbio.7b00099

  日期：2017.9.15

  The deeply red-colored natural compound prodigiosin is a representative of the prodiginine alkaloid family, which possesses bioactivities as antimicrobial, antitumor, and antimalarial agents. Various bacteria including the opportunistic human pathogen Serratia marcescens and different members of the Streptomycetaceae and Pseudoalteromonadaceae produce prodiginines. In addition, these microbes generally accumulate many structurally related alkaloids making efficient prodiginine synthesis and purification difficult and expensive. Furthermore, it is known that structurally different natural prodiginine variants display differential bioactivities. In the herein described mutasynthesis approach, 13 different derivatives of prodigiosin were obtained utilizing the GRAS (generally recognized as safe) classified strain Pseudomonas putida KT2440. Genetic engineering of the prodigiosin pathway together with incorporation of synthetic intermediates thus resulted in the formation of a so far unprecedented structural diversity of new prodiginine derivatives in P. putida. Furthermore, the formed products allow reliable conclusions regarding the substrate specificity of PigC, the final condensing enzyme in the prodigiosin biosynthesis pathway of S. marcescens. The biological activity of prodigiosin toward modulation of autophagy was preserved in prodiginine derivatives. One prodiginine derivative displayed more potent autophagy inhibitory activity than the parent compound or the synthetic clinical candidate obatoclax.
• One-pot synthesis of pyrroles from ketones, hydroxylamine, and 1,2-dibromoethane in the system KOH-DMSO
  作者：A. V. Ivanov、V. S. Shcherbakova、A. I. Mikhaleva、B. A. Trofimov

  DOI：10.1134/s1070428014120100

  日期：2014.12

  Dibutyl ketone, cyclohexanone, acetophenone, alpha-tetralone, and methyl 2-thienyl ketone were converted into the corresponding 2,3-substituted pyrroles by reaction with hydroxylamine hydrochloride and 1,2-dibromoethane in the system KOH-DMSO.