5-(4-methylthiophenyl)dipyrromethane | 305830-96-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(4-methylthiophenyl)dipyrromethane
• 英文别名: 2-[(4-methylsulfanylphenyl)-(1H-pyrrol-2-yl)methyl]-1H-pyrrole
• CAS: 305830-96-0
• 化学式: C₁₆H₁₆N₂S
• 分子量: 268.382
• InChiKey: JIXTWQMOVNVIFP-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  476.6±45.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  56.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-(4-methylthiophenyl)dipyrromethane 在 盐酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 23.0h， 生成 5-[(4-cyanophenyl)ethynyl]-15-[3,5-bis(trifluoromethyl)phenyl]-10,20-bis[4-(methylthio)phenyl]porphyrin
  参考文献：
  名称：

  高效合成具有不同内消旋取代基的卟啉，可避免在水性介质中发生争夺

  摘要：

  我们已经开发出了新的条件，可以提供区域异构纯的带有芳基和芳基乙炔基取代基的反式A 2 B 2，A 3 B和反式AB 2 C卟啉。卟啉的制备方法是：将二吡咯甲烷与醛进行酸催化缩合，然后用对氯苯醌或2,3-二氯-5,6-二氰基-1,4-苯并醌（DDQ）进行氧化。通过检查各种反应参数（例如溶剂组成，酸浓度和反应时间），可以确定最佳的缩合条件。确定的条件（对于芳族醛：EtOH / H 2 O 4：1，[DPM] = 4 m M，[醛] = 4 mM，[HCl] ＝ 38m M，16小时；m，[m / z] 。对于芳基乙炔醛：THF / H 2 O 2：1，[DPM] = 13 m M，[醛] = 13 m M，[HCl] = 150 m M，3小时）导致卟啉的形成，产率为9 –38％，无可检测的加扰。该合成与各种官能团如酯或腈相容。总共有20个新的trans- A 2 B 2-，A 3 B-和trans-

  DOI：

  10.1002/chem.201403677
• 作为产物：
  描述：

  吡咯 、 4-(甲基巯基)苯甲醛 在 三氟乙酸 作用下， 反应 0.08h， 以64.7%的产率得到5-(4-methylthiophenyl)dipyrromethane
  参考文献：
  名称：

  研究由相同单体组成的紧密耦合卟啉阵列用于多位信息存储

  摘要：

  我们基于分子的信息存储设备的现有设计采用了以弱耦合，共价连接的阵列形式组织的多个氧化还原活性单元。为了探索一种更简单的设计，我们在此报告了卟啉阵列的合成方法，其中具有相同氧化电位的卟啉直接相互连接，而不是通过分子接头连接。通过合理合成获得的与锌（II）-5,15-双（4-叔丁基苯基）-10-苯基卟啉的AgPF（6）的氧化偶合，提供了预期的二聚体，该二聚体通过介观键和意外键连接三聚体通过介观介导联系而加入。为了附着在电活性表面上，我们合成了一个介孔连接的卟啉二聚体，其中一个介孔位置带有硫醇连接基。使用S-乙酰基保护基以避免处理游离的硫醇基。锌（II）-5,10的偶联 15-三（3，5-二叔丁基苯基）卟啉（“上半部分”）和锌（II）-5- [4-（S-乙酰硫基）苯基] -10,20-双（3，5-二叔丁基苯基）卟啉（“下半部分”）提供了三种不同的内消旋连接的二聚体，其中所需的二聚体为主要产物。溶

  DOI：

  10.1021/jo000489e

文献信息

• Efficient Synthesis of meso-Substituted Corroles in a H₂O−MeOH Mixture
  作者：Beata Koszarna、Daniel T. Gryko

  DOI：10.1021/jo060007k

  日期：2006.5.1

  of various reaction parameters (cosolvent, reagent, and acid concentration), high yields of bilanes were obtained. Additionally, the bilane derived from 4-cyanobenzaldehyde was isolated, and the oxidative macrocyclization reaction was performed under various reaction conditions (different solvents, different concentrations, and various oxidants). As a result, triphenylcorrole was obtained in the highest

  开发了新的有效的条件合成内消旋取代的coroles。第一步，涉及醛与吡咯的反应，是在HCl存在下的水-甲醇混合物中进行的。通过仔细控制醛-吡咯低聚物在反应介质中的溶解度，可以获得相对较窄的分布。在对各种反应参数（助溶剂，试剂和酸浓度）进行彻底优化之后，获得了高产率的联苯胺。另外，分离出衍生自4-氰基苯甲醛的胆烷，并在各种反应条件下（不同的溶剂，不同的浓度和各种氧化剂）进行氧化大环化反应。结果，以迄今报道的最高收率（32％）获得了三苯甲酰基。研究的范围和局限性表明，该方法对于中等反应性醛和带有供电子基团的醛特别有效（收率14-27％）。在这些条件下，首次获得了带有强供电子基团的酚。另外，发现在类似条件下不受阻碍的二吡咯甲烷与醛的反应提供了反式-A 2 B酯的收率非常高（45-56％；比以前报道的高出8倍），而且没有加扰。尽管HCl浓度很高（0.3 M），但在该反应中仍未观察到加扰这一事实是前
• Access to Corrole-Appended Persubstituted Benzofurans by a Multicomponent Reaction: The Dual Role of <i>p</i>-Chloranil
  作者：Agnieszka Nowak-Król、Beata Koszarna、Maciej Krzeszewski、Trevor D. Lohrey、John Arnold、Daniel T. Gryko

  DOI：10.1021/acs.orglett.0c03133

  日期：2020.10.16

  A multicomponent reaction among dipyrranes, aryl-propargyl aldehydes, and p-chloranil leading to 10-(benzofuran-2-yl)corroles is described. p-Chloranil was identified as a crucial reagent playing a twofold role: an oxidant taking part in the formation of the corrole macrocycle and a component undergoing heteroannulation to the incipient 10-arylethynylcorrole. A series of corroles bearing persubstituted benzofuran-2-yl moieties have been synthesized, and their fundamental electronic properties have been studied via UV-vis absorption and fluorescence spectroscopies.
• DNA/Protein Binding, Molecular Docking, and in Vitro Anticancer Activity of Some Thioether-Dipyrrinato Complexes
  作者：Rakesh Kumar Gupta、Gunjan Sharma、Rampal Pandey、Amit Kumar、Biplob Koch、Pei-Zhou Li、Qiang Xu、Daya Shankar Pandey

  DOI：10.1021/ic401662d

  日期：2013.12.16

  Syntheses and characterizations of the arene ruthenium [(eta(6)-C6H6)RuCl(4-mtdpm)] (1), eta(6)-p-MeC6H4Pri?)RuCl(4-mtdpm)] (2), and structurally analogous rhodium/iridium complexes [(eta(5)-C5Me5)RhCl(4-mtdpm)] (3) and [(eta(5)-C5Me5)IrCl(4-mtdpm)] (4) [4-mtdpm = 5-(4-methylthiophenyl)-dipyrromethene] have been reported. Their identities have been established by satisfactory elemental analyses, electrospray ionization-mass spectrometry (ESI-MS), FT-IR, NMR (H-1, C-13), UV/vis, emission spectral, and electrochemical studies. Structure of the representative complex 3 has been authenticated by X-ray single crystal analyses. The complexes 1-4 effectively bind with calf thymus DNA (CT DNA) through intercalative/electrostatic interactions. In addition, these exhibit significant cytotoxicity toward Dalton lymphoma (DL) cell line and cause static quenching of the bovine serum albumin (BSA) fluorophore. The antiproliferative activity, morphological changes, and apoptosis have been evaluated by MTT assay, acridine orange/ethidium bromide (AO/EtBr) fluorescence staining, and DNA ladder assay. Mode of interaction of the complexes with DNA/protein has also been supported by molecular docking. Various studies revealed remarkable decrease in the in vitro DL cell proliferation and induction of the apoptosis by 1-4, which lies in the order 2 > 1 > 4 > 3.
• Photocurrent Generation in Multilayer Organic−Inorganic Thin Films with Cascade Energy Architectures
  作者：Feras B. Abdelrazzaq、Raymond C. Kwong、Mark E. Thompson

  DOI：10.1021/ja011700m

  日期：2002.5.1

  Zirconium organobisphosphonate multilayer thin films of viologen derivatives were grown on copper dithiolate multilayers of 5,15-di(p-thiolphenyl)-10,20-di(p-tolyl)porphyrin (POR) and 5,15-di(p-thiolphenyl)-10,20-di(p-tolyl)porphyrinzinc (ZOR) on a variety of substrates (e.g. Au, SiO2), using solution depositions methods. The multilayer structures were studied by atomic force microscopy, UV-vis spectroscopy, and ellipsometry. In the case of copper dithiolate thin films, layer-by-layer lamellar growth with low surface roughness resulted, while higher surface roughness was observed in the growth of Zr viologen bisphosphonate films. Gold electrodes modified with zirconium bisphosphonate multilayers of viologen on top of copper dithiolate multilayers of porphyrin derivatives (ZOR or POR) were photoelectroactive and produced efficient and stable photocurrents using visible light. By arranging the zinc-porphyrin (ZOR) and the free base porphyrin (POR) donors in an energetically favorable fashion, according to their redox potentials and optical energy gaps, the photoinduced charge separation was improved, and higher photocurrent quantum yields (similar to4%) and fill factor (similar to50%) of the photoelectrode were achieved.