2-nitroso-3,5-diphenyl-1H-pyrrole | 154675-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-nitroso-3,5-diphenyl-1H-pyrrole
• 英文别名: 2-nitroso-3,5-diphenylpyrrole；5-Nitroso-2,4-diphenyl-pyrrol；1H-Pyrrole, 2-nitroso-3,5-diphenyl-
• CAS: 154675-02-2
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: IBTQDCQWOPEDCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 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：
  45.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-nitroso-3,5-diphenyl-1H-pyrrole 在 10% Pd/C 、 ammonium acetate 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 (3,5-diphenyl-1H-pyrrol-2-yl)(3,5-diphenylpyrrol-2-ylidene)amine
  参考文献：
  名称：

  Mechanistic Insight into the Formation of Tetraarylazadipyrromethenes

  摘要：

  The tetraarylazadipyrromethene chromophore class has gained increasing attention in the past decade for a diverse set of scientific interests and applications. The most direct synthetic route available for their generation is heating of 4-nitro-1,3-diarylbutan-1-ones with an ammonium source in an alcohol solvent. Despite the practical simplicity, the reaction pathway(s) for these conversions are lengthy and unclear. To gain insight into the steps involved, N-15 labeling experiments with MS and NMR analysis were utilized for conversion of 4-nitro-1,3-diphenylbutan-1-one 1 into tetraphenylazadipyrromethene 2 with (NH4OAc)-N-15. To, permit examination, of later stages of the reaction sequence to 2, the N-15-labeled potential intermediate 3,5-diphenyl-1H-pyrrol-2-amine 10 was synthesized. A study of the dimerization pathway utilizing N-15-labeled 10 revealed an unprecedented nitrogen rearrangement in the final stages of the pathway involving a ring:opening/closing of a pyrrole ring. Utilizing N-15 labeling experiments we have shown that 2,4-diphenylpyrrole 8 can also react under the reaction conditions with 3,5-diphenyl-2H-pyrrol-2-imine 7 (from oxidation of 10) to. produce 2. Overall in the conversion of 1 into 2, two related pathways are ongoing concurrently, the first involves a dimerization of 3,5-diphenyl-2H-pyrrol-2-imine 7, and the other a reaction of 7 with 2,4-diphenylpyrrole 8.

  DOI：

  10.1021/jo301972w
• 作为产物：
  描述：

  4,4-dimethoxy-1,3-diphenyl-butan-1-one 在 盐酸 、 sodium nitrate 、 ammonium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 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

文献信息

• Impact of a conformationally restricted receptor on the BF2 chelated azadipyrromethene fluorosensing platform
  作者：John Killoran、Donal F. O'Shea

  DOI：10.1039/b513878g

  日期：——

  Conformational control of the receptor–fluorophore orientation of BF2 chelated azadipyrromethene sensors reveals two photophysically different modes of analyte triggered fluorescence switching both of which exhibit large off–on fluorescence intensity responses to the light input–output of the sensors in the visible red spectral region.

  对 BF2螯合偶氮二吡咯并吡喃传感器的受体-荧光团取向的构象控制揭示了两种光物理上不同的分析物触发荧光切换模式，这两种模式在可见光红色光谱区都对传感器的光输入-输出表现出较大的关断-开启荧光强度响应。
• PET modulated fluorescent sensing from the BF2 chelated azadipyrromethene platform
  作者：Michael J. Hall、Lorcan T. Allen、Donal F. O'Shea

  DOI：10.1039/b514788c

  日期：——

  A convergent building block synthesis has been applied to new off/on photoinduced electron transfer (PET) modulated fluorescent sensors which are based on a BF2 chelated tetraarylazadipyrromethene platform and operate in the biomedically important red region of the visible spectrum. Incorporation of diethylamine and morpholine receptors facilitates off/on microenvironment polarity and pH sensing. Aqueous formulation and in vitro cellular imaging demonstrates their potential for intracellular sensing.

  新的关/开光诱导电子转移（PET）调制荧光传感器基于 BF2 螯合四芳基氮杂吡咯并菲平台，可在可见光谱中具有重要生物医学意义的红色区域工作。二乙胺和吗啉受体的加入促进了微环境极性和 pH 值的关/开传感。水性配方和体外细胞成像证明了它们在细胞内传感方面的潜力。
• 荧光染料、磁性荧光编码微球及其制备方法和应用
  申请人：苏州纳微生命科技有限公司

  公开号：CN116813654A

  公开（公告）日：2023-09-29

  本发明涉及一种荧光染料、磁性荧光编码微球及其制备方法和应用。上述荧光染料具有如下结构通式：#imgabs0#，其中，R1及R2各自独立地包括苯基、噻吩基、C1~C6烷基取代的噻吩基及C3~C10杂芳基取代的噻吩基中的任一种或几种的组合，R3包括碳碳双键，R4包括C1~C6烷基。上述荧光染料的稳定性好，波长适宜，能够应用在磁性荧光编码微球的制备中。
• Visible Fluorescence Chemosensor for Saxitoxin
  作者：Robert E. Gawley、Hua Mao、M. Mahbubul Haque、John B. Thorne、Jennifer S. Pharr

  DOI：10.1021/jo062506r

  日期：2007.3.1

  Absorption spectra of a number of shellfish extracts have been obtained and reveal prominent absorptions in all samples at 210 and 260 nm and at 325 nm in some of them. These absorptions preclude the use of chromophores with similar absorptions in testing of shellfish samples for paralytic shellfish toxins. Two crown ether chemosensors featuring a boron azadipyrrin chromophore have been synthesized; both have absorption maxima at 650 nm, where all the shellfish extracts are transparent. The synthetic sensors feature either 18- or 27-membered crown ether rings and have been evaluated as visible sensors for the paralytic shellfish toxin saxitoxin. The binding constant for one of them is in the range of 3-9 x 10(5) M-1 and exhibits a fluorescence enhancement of over 100% at 680 nm in the presence of 40 mu M saxitoxin.
• 157. 2 : 4-Diarylpyrroles. Part II. Methines
  作者：Maurice A. Thorold Rogers

  DOI：10.1039/jr9430000596

  日期：——