2,4-二苯基吡咯 | 3274-56-4

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2,4-二苯基吡咯
• 英文名称: 2,4-diphenylpyrrole
• 英文别名: 2,4-diphenyl-1H-pyrrole
• CAS: 3274-56-4
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: FSBPQTRUHOMNPG-UHFFFAOYSA-N

物化性质

• 熔点：
  179-180 °C(Solv: benzene (71-43-2))
• 沸点：
  416.4±24.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)
• 保留指数：
  1790;1790

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H317
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  2,4-二苯基吡咯 在 盐酸 、 sodium nitrate 作用下， 以 乙醇 为溶剂， 以79%的产率得到2-nitroso-3,5-diphenyl-1H-pyrrole
  参考文献：
  名称：

  A Modular Synthesis of Unsymmetrical Tetraarylazadipyrromethenes

  摘要：

  A stepwise route to unsymmetrical tetraarylazadipyrromethenes by a condensation of 2,4-diaryl-5-nitroso-pyrroles with 2,4-diarylpyrroles is described. This modular building-block approach allows for the introduction of up to four different aryl substituents on the azadipyrromethene and is tolerant of a varied substituent set. An efficient synthesis of the 2,4-diarylpyrroles building blocks from 1,3-diaryl-4-nitro-butan-1-ones by nitro hydrolysis to a keto-aldehyde and subsequent ammonia condensation reaction has been achieved. The facile conversion of 2,4-diarylpyrroles into their alpha-nitroso analogues by their reaction with sodium nitrite generated the second building block required for the synthesis.

  DOI：

  10.1021/jo050696k
• 作为产物：
  描述：

  4,4-dimethoxy-1,3-diphenyl-butan-1-one 在 ammonium acetate 、 溶剂黄146 作用下， 反应 1.0h， 以0.31 g的产率得到2,4-二苯基吡咯
  参考文献：
  名称：

  A Modular Synthesis of Unsymmetrical Tetraarylazadipyrromethenes

  摘要：

  A stepwise route to unsymmetrical tetraarylazadipyrromethenes by a condensation of 2,4-diaryl-5-nitroso-pyrroles with 2,4-diarylpyrroles is described. This modular building-block approach allows for the introduction of up to four different aryl substituents on the azadipyrromethene and is tolerant of a varied substituent set. An efficient synthesis of the 2,4-diarylpyrroles building blocks from 1,3-diaryl-4-nitro-butan-1-ones by nitro hydrolysis to a keto-aldehyde and subsequent ammonia condensation reaction has been achieved. The facile conversion of 2,4-diarylpyrroles into their alpha-nitroso analogues by their reaction with sodium nitrite generated the second building block required for the synthesis.

  DOI：

  10.1021/jo050696k

文献信息

• NOVEL TYPE OF TRANSFORMATIONS OF α-AZIDOSTYRENE DERIVATIVES AND 3-ARYL-2<i>H</i>-AZIRINES IN THE PRESENCE OF HEXACARBONYLMOLYBDENUM
  作者：Makoto Nitta、Tomoshige Kobayashi

  DOI：10.1246/cl.1983.1715

  日期：1983.11.5

  The reaction of α-azidostyrene derivatives with hexacarbonylmolybdenum was found to give 2,5-diarylpyrroles and acetophenone derivatives via a complexed 1-arylvinylnitrene intermediate, while that of 3-aryl-2H-azirines gave 2,4-diarylpyrroles in addition to acetophenone derivatives and 2,5-diarylpyrazines.

  发现 α-叠氮苯乙烯衍生物与六羰基钼的反应通过络合的 1-芳基乙烯基硝基中间体产生 2,5-二芳基吡咯和苯乙酮衍生物，而 3-芳基-2H-吖啶的反应除苯乙酮衍生物外还产生 2,4-二芳基吡咯和 2,5-二芳基吡嗪。
• Efficient Far-Red/Near-IR Absorbing BODIPY Photocages by Blocking Unproductive Conical Intersections
  作者：Pradeep Shrestha、Komadhie C. Dissanayake、Elizabeth J. Gehrmann、Chamari S. Wijesooriya、Atreyee Mukhopadhyay、Emily A. Smith、Arthur H. Winter

  DOI：10.1021/jacs.0c07139

  日期：2020.9.9

  Photocages are light-sensitive chemical protecting groups that give investigators control over activation of biomolecules using targeted light irradiation. A compelling application of far-red/near-IR absorbing photocages is their potential for deep tissue activation of biomolecules and phototherapeutics. Towards this goal, we recently reported BODIPY photocages that absorb near-IR light. However, these

  光笼是光敏化学保护基团，使研究人员可以使用靶向光照射控制生物分子的激活。远红/近红外吸收光笼的一个引人注目的应用是它们在生物分子和光疗法的深层组织激活方面的潜力。为了实现这一目标，我们最近报道了吸收近红外光的 BODIPY 光笼。然而，与较短波长的吸收光笼相比，这些光笼的光释放效率降低，这阻碍了它们的应用。由于光化学是速率的零和竞争，因此可以通过使所需的光反应更有效或通过阻碍竞争性衰变通道来提高光反应的量子产率。后一种抑制非生产性衰变通道的策略旨在通过合成阻止进入非生产性单线态内部转换锥形交叉点的结构来提高长波长吸收 BODIPY 光笼的释放效率，这些交叉点最近已从激发态动态模拟中定位为简单的 BODIPY 结构. 这种策略导致合成了新的构象限制硼甲基化 BODIPY 光笼，其在 700 nm 附近强烈吸收光。在最好的情况下，光笼的消光系数为 124,000 M-1cm-1，光释放的量子产率为
• Stepwise iododesilylation and coupling reaction: a flexible route to 2,4-disubstituted-1H-pyrroles
  作者：Jianhui Liu、Nanyan Fu、Changyun Wei、Zhucao Song

  DOI：10.1016/j.tetlet.2016.04.105

  日期：2016.6

  In this study, we report a new strategy for the synthesis of 2,4-disubstituted pyrroles using a stepwise iododesilylation and palladium-catalysed Suzuki coupling reaction of 2,4-bis(trimethylsilyl)-1-t-Boc-1H-pyrrole (2). The regioselective iodo-desilylation followed by the Suzuki coupling reaction with concomitant Boc deprotection are critical aspects of the new synthesis method.

  在这项研究中，我们报告了一种新的策略，用于使用2,4-双（三甲基甲硅烷基）-1- t -Boc-1 H-吡咯的逐步碘代硅烷化和钯催化的Suzuki偶联反应合成2,4-二取代的吡咯（2）。新的合成方法的关键方面是在区域选择性的碘-去甲硅烷基化反应之后进行铃木偶联反应以及伴随的Boc脱保护。
• Simple two-step synthesis of 2,4-disubstituted pyrroles and 3,5-disubstituted pyrrole-2-carbonitriles from enones
  作者：Murat Kucukdisli、Dorota Ferenc、Marcel Heinz、Christine Wiebe、Till Opatz

  DOI：10.3762/bjoc.10.44

  日期：——

  The cyclocondensation of enones with aminoacetonitrile furnishes 3,4-dihydro-2H-pyrrole-2-carbonitriles which can be readily converted to 2,4-disubstituted pyrroles by microwave-induced dehydrocyanation. Alternatively, oxidation of the intermediates produces 3,5-disubstituted pyrrole-2-carbonitriles.

  烯酮与氨基乙腈的环缩合反应得到 3,4-dihydro-2H-pyrrole-2-carbonitriles，可通过微波诱导脱氢氰化很容易地将其转化为 2,4-二取代的吡咯。或者，中间体的氧化产生 3,5-二取代的吡咯-2-腈。
• Gold(I)-Catalyzed Cascade Hydroarylation/Cycloaromatization to Indolizines via Pyridine Ring Construction
  作者：Xiangdong Li、Xin Xie、Yuanhong Liu

  DOI：10.1021/acs.joc.6b00346

  日期：2016.5.6

  An efficient and atom-economic method for the synthesis of multisubstituted indolizines via gold-catalyzed cascade hydroarylation/cycloaromatization reaction of α-(N-pyrrolyl)ketones with alkynes is described. The reaction is realized through the construction of the pyridine ring of indolizines, which allows the regioselective incorporation of a wide range of functionalities on the pyridine unit.

  描述了一种通过金催化的α-（N-吡咯基）酮与炔烃的级联加氢芳基化/环芳烃化反应合成多取代的吲哚嗪的有效且经济的方法。该反应是通过构建吲哚嗪的吡啶环来实现的，该吲哚并嗪的吡啶环可以在吡啶单元上区域选择性地结合多种官能团。

表征谱图