ethyl 4-hexyl-3,5-dimethylpyrrole-2-carboxylate | 4758-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 4-hexyl-3,5-dimethylpyrrole-2-carboxylate
• 英文别名: 2-Ethoxycarbonyl-4-hexyl-3,5-dimethylpyrrole；ethyl 4-hexyl-3,5-dimethyl-1H-pyrrole-2-carboxylate
• CAS: 4758-65-0
• 化学式: C₁₅H₂₅NO₂
• 分子量: 251.369
• InChiKey: LOXPERIWJSOOAG-UHFFFAOYSA-N

物化性质

• 沸点：
  367.4±30.0 °C(Predicted)
• 密度：
  0.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 4-hexyl-3,5-dimethylpyrrole-2-carboxylate 在 platinum(IV) oxide 、 palladium on activated charcoal 磺酰氯 、 氢气 、 碘 、 sodium acetate 、 sodium 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 50.0~90.0 ℃ 、2.13 kPa 条件下， 反应 73.67h， 生成 benzyl 3-hexyl-4-methylpyrrole 2-carboxylate
  参考文献：
  名称：

  Aryl Ring Rotation in Porphyrins. A Carbon-13 NMR Spin−Lattice Relaxation Time Study

  摘要：

  Overall tumbling and internal rotational motions in porphyrins bearing meso aryl substituents and, in some cases, flanking alkyl groups at the beta-pyrrolic positions have been determined using C-13 spin-lattice relaxation time measurements. In deuteriochloroform solution at 303 K, the overall reorientation of all three porphyrins investigated occurs with diffusion coefficients of similar to 1 x 10(9) s(-1). In porphyrins with only hydrogen at the beta-pyrrolic positions, the meso phenyl rings undergo rotations about their single bonds to the porphyrin with diffusion coefficients of similar to 4 x 10(9) s(-1). Introduction of methyl substituents at the beta-pyrrolic positions adjacent to the phenyl rings reduces these motions, but only to similar to 1 x 10(9) s(-1). Thus, significant internal motions are present in both types of molecules. These motions occur on the time scale of many photoinduced electron and energy transfer processes in porphyrins covalently linked to electron or energy donors or accepters through meso aryl groups. Thus, the internal librational motions may affect rates of photoinduced electron and energy transfer, even in relatively ''rigid'' molecular constructs.

  DOI：

  10.1021/jp962209y
• 作为产物：
  描述：

  2-壬酮 以78%的产率得到ethyl 4-hexyl-3,5-dimethylpyrrole-2-carboxylate
  参考文献：
  名称：

  Brown, David; Griffiths, David; Rider, Margaret E., Journal of the Chemical Society. Perkin transactions I, 1986, p. 455 - 464

  摘要：

  DOI：

文献信息

• Thermal oxidative degradation of the functionally substituted 2,2′-dipyrrolylmethenes hydrobromides and difluoroborates
  作者：S. L. Yutanova、M. B. Berezin、A. S. Semeikin、E. V. Antina、G. B. Guseva、A. I. V’yugin

  DOI：10.1134/s1070363213030237

  日期：2013.3

  Thermal oxidative decomposition of samples of crystalline hydrobromide and borofluoride complexes (BODIPY) of a series of 2,2′-dipyrrolylmethenes (HL) was studied by means of thermogravimetry in an atmosphere of air oxygen. An increase in the degree and symmetry of substitution, aromaticity, and the length of the substituents in 4,4′-positions of the pyrrole ligand rings increases stability of the

  在空气氧气氛中，通过热重分析法研究了一系列2,2'-二吡咯基亚甲基（HL）的结晶氢溴酸盐和硼氟化物配合物（BODIPY）样品的热氧化分解。吡咯配体环的4，4′-位的取代度和对称性，芳香性和取代基的长度的增加，增加了BODIPY染料对氧化降解的稳定性。进行了结构因素对氢溴化物（HL·HBr），d-金属（ML 2）和硼（III）与2,2'-二吡咯基亚甲基配合物的热解性的影响的比较分析。
• Thermochemistry of substituted pyrroles
  作者：M. V. Berezin、A. S. Semeikin、A. I. V'yugin、G. A. Krestov

  DOI：10.1007/bf00698428

  日期：1993.3

  The heats of solution of a series of substituted pyrroles in benzene, carbon tetrachloride, chloroform, DMF, and pyridine were measured by a calorimetric method at 298.15 K. The influence of substituents in the pyrrole molecule on the energy parameters of solvation by organic solvents is discussed.

  一系列取代的吡咯在苯、四氯化碳、氯仿、DMF和吡啶中的溶解热在298.15 K下通过量热法测量。吡咯分子中的取代基对有机溶剂溶剂化能量参数的影响为讨论。
• Synthesis of Chrysoporphyrins and a Related Benzopyrene-Fused System
  作者：Timothy D. Lash、Melissa A. Mathius、Deyaa I. AbuSalim

  DOI：10.1021/acs.joc.2c01859

  日期：2022.12.16

  Reaction of 6-nitrochrysene with ethyl isocyanoacetate in the presence of a non-nucleophilic base gave a c-annulated pyrrole ethyl ester that was used to prepare chrysene-fused tripyrranes and a chrysopyrrole dialdehyde. Chrysene-fused tripyrranes were reacted with a pyrrole dialdehyde, but poor yields of chrysoporphyrins were obtained. However, condensation of the chrysopyrrole dialdehyde with a series

  6-硝基屈与异氰基乙酸乙酯在非亲核碱存在下反应得到c-环化吡咯乙酯，用于制备屈烯稠合三吡喃和金吡咯二醛。将 Chrysene-fused tripyrranes 与吡咯二醛反应，但获得的金卟啉收率很低。然而，金吡咯二醛与一系列三吡喃的缩合提供了优异的金卟啉和苊-金卟啉收率。氯化铁 (III) 介导的二己基菊卟啉的氧化环化提供了一种苯并芘稠合卟啉，它表现出强烈的红移电子吸收光谱。DFT 计算表明，金卟啉和苯并芘稠合卟啉都具有互变异构体，这些互变异构体具有通过卟啉核和稠合多环芳烃 (PAH) 单元的 34π 电子离域途径。c-环化吡咯二醛也与卡巴三吡林缩合，生成 PAH 稠合卡巴卟啉，保留了完全的芳香特性。
• Berezin, M. B.; Semeikin, A. S.; V'yugin, A. I., Russian Journal of Physical Chemistry, 1996, vol. 70, # 8, p. 1265 - 1268
  作者：Berezin, M. B.、Semeikin, A. S.、V'yugin, A. I.

  DOI：——

  日期：——