bis(3-ethyl-4-methyl-1H-pyrrol-2-yl)methane | 92415-30-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: bis(3-ethyl-4-methyl-1H-pyrrol-2-yl)methane
• 英文别名: bis(3-ethyl-4-methyl-2-pyrrolyl)methane；3,3'-diethyl-4,4'-dimethyldipyrrolylmethane；1H-Pyrrole, 2,2'-methylenebis[3-ethyl-4-methyl-；3-ethyl-2-[(3-ethyl-4-methyl-1H-pyrrol-2-yl)methyl]-4-methyl-1H-pyrrole
• CAS: 92415-30-0
• 化学式: C₁₅H₂₂N₂
• 分子量: 230.353
• InChiKey: LCEZKXQCADGXOI-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60 °C
• 沸点：
  359.9±37.0 °C(Predicted)
• 密度：
  1.029±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  bis(3-ethyl-4-methyl-1H-pyrrol-2-yl)methane 在 氢溴酸 、 溶剂黄146 作用下， 以 氯仿 、 正丁醇 为溶剂， 生成 10-phenyl-(2,18-diethyl-3,7,8,12,13,17-hexamethyl)porphyrin, zinc complex
  参考文献：
  名称：

  质子-供体介质中2,3,7,8,12,18-六甲基-5-苯基-13,17-二乙基卟啉及其氮取代类似物的锌，铜，钴和锰配合物的合成和离解动力学

  摘要：

  在卟啉核的10和20位以及苯环的对位带有硝基的硝基取代的2,3,7,7,8,12,18-六甲基-5-苯基-13,17-二乙基卟啉已经合成。所获得的化合物的结构已通过H 1 NMR，UV和IR光谱以及质谱法得到证实。研究了在质子供体介质中获得的卟啉的锌，铜，钴和锰配合物的解离动力学。卟啉金属配合物的稳定性与四吡咯循环中取代基的电子效应和后者的空间畸变有关。

  DOI：

  10.1134/s1070363219040169
• 作为产物：
  描述：

  5,5-亚甲基双(4-乙基-3-甲基-2-吡咯羧酸二乙酯) 在 sodium hydroxide 作用下， 以89%的产率得到bis(3-ethyl-4-methyl-1H-pyrrol-2-yl)methane
  参考文献：
  名称：

  Simple Methodology for the Synthesis of meso-Unsubstituted β-Substituted Alkyl Porphyrins

  摘要：

  无内消旋的β-烷基二吡咯甲烷与不同的无内消旋的1,9-双(甲酰基)二吡咯甲烷的麦克唐纳[2+2]型缩合产生新的不对称空间无阻碍的卟啉。

  DOI：

  10.1055/s-2006-950263

文献信息

• Synthesis and Structure–Activity Relationships of Tambjamines and B-Ring Functionalized Prodiginines as Potent Antimalarials
  作者：Papireddy Kancharla、Jane Xu Kelly、Kevin A. Reynolds

  DOI：10.1021/acs.jmedchem.5b00560

  日期：2015.9.24

  Synthesis and antimalarial activity of 94 novel bipyrrole tambjamines (TAs) and a library of B-ring functionalized tripyrrole prodiginines (PGs) against a panel of Plasmodium falciparum strains are described. The activity and structure–activity relationships demonstrate that the ring-C of PGs can be replaced by an alkylamine, providing for TAs with retained/enhanced potency. Furthermore, ring-B of

  描述了94种新型联吡咯他布明胺（TAs）的合成和抗疟活性以及针对一系列恶性疟原虫菌株的B环功能化三联吡咯酮（PGs）库。活性和结构-活性之间的关系表明，PGs的C环可以被烷基胺取代，从而为TAs提供保留/增强的效力。此外，PG / TA的B环可以在4位（取代OMe）或3位和4位上被短烷基取代而不影响效能。已评估了八个代表性TA和两个PG对耐多药疟原虫的抗疟活性口服给药的小鼠剂量范围为5-100 mg / kg×4天。KAR425 TA的功效比以前任何PG所观察到的都要大，在25天和50 mg / kg×4天的剂量下，直到28天之前，对感染疟疾的小鼠提供100％的保护，并且在该模型中也可以单次口服治疗（80毫克/公斤）。这项研究提出了TAmbjamines中抗疟活性的第一个解释。
• [EN] TAMBJAMINES AND B-RING FUNCTIONALIZED PRODIGININES<br/>[FR] TAMBJAMINES ET PRODIGININES FONCTIONNALISÉES À CYCLE B
  申请人：UNIV PORTLAND STATE

  公开号：WO2016176450A1

  公开（公告）日：2016-11-03

  Embodiments of tambjamines and B-ring functionalized prodiginines are disclosed. Methods of synthesizing and using the disclosed compounds are also disclosed. Some embodiments of the disclosed compounds have antimalarial activity. Certain embodiments of the disclosed compounds have been shown to clear parasitemia in mice, and/or are curative in a single dose without toxicity.

  本文披露了tambjamine和B环功能化的prodiginines的实施例。还披露了合成和使用所披露化合物的方法。所披露化合物的一些实施例具有抗疟活性。已经证明所披露化合物的某些实施例能够清除小鼠体内的寄生虫，或者在单剂量下具有治愈作用且无毒性。
• Thermotropic phase transitions in 5,15-bis(4-alkoxyphenyl)octaalkylporphyrins
  作者：Ernst J. R. Sudhöulter、Marinus van Dijk、Cees J. Teunis、Georgine M. Sanders、Sybolt Harkema、Gerrit M. H. van de Velde、Pieter G. Schouten、John M. Warman

  DOI：10.1039/jm9960600357

  日期：——

  Nineteen novel alkyl substituted porphyrins have been synthesized and their thermal phase behaviour has been investigated in detail. Twelve compounds showed a reversible phase transition below the isotropization temperature. From time resolved microwave conductivity (TRMC) measurements and powder X-ray diffractometry it was concluded that the molecular packing does not change significantly at the lower phase transition temperature and that the porphyrin cores occupy isolated positions. Single X-ray diffraction measurements showed that the porphyrins are arranged in a layered structure and that the space between the layers is occupied by the alkyl substituents of the pyrrole units. The phase transitions at the lower temperature were therefore identified as changes in the crystal ordering of the porphyrins.

  合成了19种新型烷基取代卟啉，并详细研究了它们的热相行为。其中12种化合物在各向同性化温度以下显示可逆的相变。通过时间分辨微波电导率（TRMC）测量和粉末X射线衍射分析得出结论：在较低的相变温度下，分子排列没有显著改变，卟啉核心占据孤立位置。单晶X射线衍射测量显示，卟啉呈层状排列，层间由吡咯单元的烷基取代基占据。因此，低温下的相变被确定为卟啉晶体有序性的变化。
• Synthesis and photophysical properties of porphyrins containing viologen units for ultrafast molecular photonics
  作者：Robert Laudien、Iori Yoshida、Toshihiko Nagamura

  DOI：10.1039/b202991j

  日期：——

  Several 5,15-diarylporphyrin derivatives containing viologen units as an electron acceptor for ultrafast intramolecular electron transfer have been synthesized. The fluorescence of the porphyrin–viologen linked systems was appreciably quenched by the attached viologens. In accordance with this, the formation of a charge-separated state was observed upon excitation with a femtosecond (fs) laser at 400 nm. The rate of electron transfer and back transfer was controlled by the different length of alkyl chain spacers between porphyrin and viologen. Attempts to use these porphyrin molecules as a thin film component of ultrafast parallel data processing by guided wave mode geometry were limited by gradual deterioration upon repeated fs laser excitation.

  合成了几种含有紫精单元作为电子受体的5,15-二芳基卟啉衍生物，用于超快分子内电子转移。连接的紫精单元显著淬灭了卟啉-紫精体系的荧光。与此一致，在400 nm飞秒激光激发下观察到电荷分离态的形成。电子转移和逆转移的速率受控于卟啉和紫精之间不同长度的烷基链间隔物。试图将这些卟啉分子用作通过波导模式几何结构的薄膜组件，用于超快并行数据处理，但由于反复飞秒激光激发导致的逐渐退化而受到限制。
• Synthesis and characterization of novel cobalt aluminum cofacial porphyrins. First crystal and molecular structure of a heterobimetallic biphenylene pillared cofacial diporphyrin
  作者：Roger Guilard、Michel Angel Lopez、Alain Tabard、Philippe Richard、Claude Lecomte、Stephane Brandes、James E. Hutchison、James P. Collman

  DOI：10.1021/ja00051a021

  日期：1992.12

  The synthesis of the novel family of heterodinuclear complexes (DP)CoAl(OR) (where DP 4- is the tetraanion of the diporphyrin biphenylene DPB or the diporphyrin anthracene DPA, and R=CH 3 , CH 2 CH 3 , or CH 2 C 6 H 5 ) is reported. These complexes were obtained by selective metalation of the cofacial diporphyrins with cobalt and aluminium. Each (DP)CoAl(OR) complex was characterized by mass spectrometry

  新型异双核配合物家族 (DP)CoAl(OR) 的合成（其中 DP 4- 是双卟啉联苯 DPB 或双卟啉蒽 DPA 的四阴离子，并且 R=CH 3 、CH 2 CH 3 或 CH 2 C 6 H 5 ) 被报道。这些配合物是通过用钴和铝对共面二卟啉进行选择性金属化而获得的。每个 (DP)CoAl(OR) 复合物都通过质谱和 UV-vis、IR、ESR 和 1 H NMR 光谱进行表征。