(1H-pyrrol-2-yl)(thiophen-2-yl)methanone | 13169-77-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (1H-pyrrol-2-yl)(thiophen-2-yl)methanone
• 英文别名: Pyrrylthiophenylketon；2-(Thiophen-2-carbonyl)-pyrrol；2-Pyrrolyl-2-thienyl-keton；pyrrol-2-yl-thiophen-2-yl-methanone；pyrrol-2-yl-[2]thienyl ketone；Pyrrol-2-yl-[2]thienyl-keton；2-(2-thenoyl)pyrrole；1H-pyrrol-2-yl(thiophen-2-yl)methanone
• CAS: 13169-77-2
• 化学式: C₉H₇NOS
• 分子量: 177.227
• InChiKey: AXJJTTNDICIXGV-UHFFFAOYSA-N

物化性质

• 熔点：
  75 °C
• 沸点：
  208-210 °C(Press: 23 Torr)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1H-pyrrol-2-yl)(thiophen-2-yl)methanone 在 aluminum oxide 、 氢氧化钾 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 4.0h， 生成 3,3'-(2-hydroxy-1⁴,3⁴-dimethyl-3¹H-1,3,5(2,5)-tripyrrola-7(2,5)-thiophena-cyclooctaphane-1(2),4,6,7(8)-tetraene-1³,3³-diyl)-bis-propionic acid diethyl ester
  参考文献：
  名称：

  Clezy,P.S.; Diakiw,V., Australian Journal of Chemistry, 1971, vol. 24, p. 2665 - 2677

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基噻吩 在 selenium(IV) oxide 、 dipotassium peroxodisulfate 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 (1H-pyrrol-2-yl)(thiophen-2-yl)methanone
  参考文献：
  名称：

  Minisci反应条件下富电子吡咯的芳构化。

  摘要：

  据报道，在无银中性条件下富电子吡咯的Minisci酰化反应的发展具有无（NH）吡咯的区域选择性单酰化的特征。与常规的Minisci条件不同，避免任何可能导致吡咯聚合的酸是成功的关键。由芳基乙醛酸原位产生的亲核酰基自由基的uppolung反应性可以帮助解释富电子吡咯产物形成的机理。备选地，提出了缺电子的吡咯自由基阳离子上的酰基的亲核取代。

  DOI：

  10.1021/acs.orglett.0c00041

文献信息

• Ketopyrroles useful as ligands in organic iridium compositions
  申请人：Chichak Kelly Scott

  公开号：US20080027028A1

  公开（公告）日：2008-01-31

  The present invention provides novel ketopyrroles having structure XXIV wherein R 2 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cyclcoaliphatic radical; “a” is an integer from 0 to 3; and X 1 and X 2 are independently at each occurrence a bromine atom, a hydroxy group, or the group OR 10 , and wherein the group R 10 is independently at each occurrence a deuterium atom, a halogen, a nitro group, an amino group, a C 3 -C 40 aromatic radical, a C 1 -C 50 aliphatic radical, or a C 3 -C 40 cyclcoaliphatic radical. Ketopyrroles XXIV are useful ligands for the preparation of Type (1) and Type (2) organic iridium compositions. In one aspect, the present invention provides deuterated analogs of XXIV. Organic iridium compositions are useful in the preparation optoelectronic devices, such as OLED devices and photovoltaic devices exhibiting enhanced performance characteristics.

  本发明提供了具有结构XXIV的新型酮吡咯，其中R2在每次出现时独立地是氘原子、卤素、硝基、氨基、C3-C40芳香基、C1-C50脂肪基或C3-C40环脂基；“a”是从0到3的整数；X1和X2在每次出现时独立地是溴原子、羟基或基团OR10，其中基团R10在每次出现时独立地是氘原子、卤素、硝基、氨基、C3-C40芳香基、C1-C50脂肪基或C3-C40环脂基。酮吡咯XXIV是用于制备类型（1）和类型（2）有机铱配合物的有用配体。在一个方面，本发明提供了XXIV的氘代物。有机铱配合物在制备光电子器件方面很有用，例如OLED器件和光伏器件，表现出增强的性能特征。
• Synthesis of novel 1,3-disubstituted pyrrolo[1,2-a]pyrazine derivatives and antiproliferative effects on glioblastoma cell line
  作者：Meltem Tan Uygun

  DOI：10.1007/s00706-021-02761-3

  日期：2021.5

  Novel pyrrolopyrazine derivatives were synthesized according to a very simple protocol starting from N-propargylated-2-acyl-pyrroles. These derivatives were obtained in good to excellent yields (68–94%) in the presence of ammonium acetate and Cs2CO3, and then subjected to cytotoxicity testing against glioblastoma cell line T98G. Among the tested molecules, those that cause 68.9%, 59.1%, and 37.5% cell

  根据非常简单的方案，从N-炔丙基化-2-酰基-吡咯开始合成新的吡咯并吡嗪衍生物。这些衍生物在乙酸铵和Cs 2 CO 3的存在下以良好至极好的收率（68–94％）获得，然后针对成胶质细胞瘤细胞系T98G进行了细胞毒性测试。在测试的分子中，那些导致68.9％，59.1％和37.5％细胞死亡的分子被鉴定为先导化合物。结构-活性关系（SAR）研究表明，构象，π-π相互作用和卤素键可能对效率很重要。最后，对吡咯并吡嗪衍生物的理论ADMET研究表明，药代动力学阶段是合适的。 图形摘要
• ORGANIC IRIDIUM COMPOSITIONS AND THEIR USE IN ELECTRONIC DEVICES
  申请人：Chichak Kelly Scott

  公开号：US20100051869A1

  公开（公告）日：2010-03-04

  The present invention provides compositions comprising at least one novel organic iridium compound which comprises at least one cyclometallated ligand and at least one ketopyrrole ligand. The organic iridium compositions of the present invention are referred to as Type (1) organic iridium compositions and are constituted such that no ligand of the novel organic iridium compound has a number average molecular weight of 2,000 grams per mole or greater (as measured by gel permeation chromatography). Type (1) organic iridium compositions are referred to herein as comprising “organic iridium complexes”. The novel organic iridium compositions are useful in optoelectronic electronic devices such as OLED devices and photovoltaic devices. In one aspect, the invention provides novel organic iridium compositions useful in the preparation of OLED devices exhibiting enhanced color properties and light output efficiencies.

  本发明提供了一种组合物，包括至少一种新型有机铱化合物，其中包括至少一种环金属配体和至少一种酮吡咯配体。本发明的有机铱组合物称为类型（1）有机铱组合物，并且构成如下：新型有机铱化合物的任何配体的数量平均分子量不大于2,000克/摩尔（通过凝胶渗透色谱测量）。类型（1）有机铱组合物在本文中称为“有机铱配合物”。新型有机铱组合物在光电子器件中非常有用，例如OLED器件和光伏器件。在一方面，本发明提供了新型有机铱组合物，可用于制备具有增强颜色性能和光输出效率的OLED器件。
• Organic iridium compositions and their use in electronic devices
  申请人：Chichak Kelly Scott

  公开号：US20080023671A1

  公开（公告）日：2008-01-31

  The present invention provides compositions comprising at least one novel polymeric organic iridium compound which comprises at least one cyclometallated ligand and at least one ketopyrrole ligand. The polymeric organic iridium compositions of the present invention are referred to as Type (2) organic iridium compositions and are constituted such that at least one ligand of the novel organic iridium compound has a number average molecular weight of 2,000 grams per mole or greater (as measured by gel permeation chromatography). Type (2) organic iridium compositions are referred to herein as comprising “polymeric organic iridium complexes”. The novel organic iridium compositions are useful in optoelectronic electronic devices such as OLED devices and photovoltaic devices. In one aspect, the invention provides novel organic iridium compositions useful in the preparation of OLED devices exhibiting enhanced color properties and light output efficiencies.

  本发明提供了至少包含一种新型聚合有机铱化合物的组成物，该聚合有机铱化合物包括至少一个环金属配体和至少一个酮吡咯配体。本发明的聚合有机铱化合物被称为Type(2)有机铱化合物，其构成至少包含一种新型有机铱化合物的配体的数量平均分子量为2,000克/摩尔或更高（通过凝胶渗透色谱法测量）。Type(2)有机铱化合物在此被称为“聚合有机铱配合物”。新型有机铱化合物在光电子器件中非常有用，例如OLED器件和光伏器件。在一方面，本发明提供了用于制备显示增强色彩性能和光输出效率的OLED器件的新型有机铱化合物。
• Method for preparing polymeric organic iridium compositions
  申请人：Cella James Anthony

  公开号：US20080026477A1

  公开（公告）日：2008-01-31

  The present invention provides a method for the preparation of polymeric organic iridium complexes useful in electronic devices such as OLEDs. The method provides polymeric organic iridium compositions comprising at least one cyclometallated ligand and at least one ketopyrrole ligand. The polymeric organic iridium compositions provided are referred to as Type (2) organic iridium compositions and are constituted such that at least one ligand of the polymeric organic iridium compound has a number average molecular weight of 2,000 grams per mole or greater (as measured by gel permeation chromatography). Type (2) organic iridium compositions are referred to herein as comprising “polymeric organic iridium complexes”. In one embodiment, the method comprises providing a non-polymeric organic iridium complex comprising one or more reactive functional groups and carrying out a polymerization step to provide the polymeric organic iridium complex comprising at least one cyclometallated ligand and at least one ketopyrrole ligand.

  本发明提供了一种用于制备聚合有机铱配合物的方法，该配合物在电子设备如OLED中有用。该方法提供了聚合有机铱组合物，该组合物包括至少一个环金属配体和至少一个酮吡咯配体。所提供的聚合有机铱组合物被称为第二型有机铱组合物，并且至少该聚合有机铱化合物的一个配体具有2,000克/摩尔或更大的数量平均分子量（通过凝胶渗透色谱测量）。本文中称为“聚合有机铱配合物”的第二型有机铱组合物。在一种实施例中，该方法包括提供一种非聚合有机铱配合物，该配合物包括一个或多个反应性功能基团，并进行聚合步骤，以提供包括至少一个环金属配体和至少一个酮吡咯配体的聚合有机铱配合物。