2,4-dibenzoylpyrrole | 147088-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dibenzoylpyrrole
• 英文别名: (4-benzoyl-1H-pyrrol-2-yl)-phenylmethanone
• CAS: 147088-89-9
• 化学式: C₁₈H₁₃NO₂
• 分子量: 275.307
• InChiKey: QRLIZYQRZOGUCC-UHFFFAOYSA-N

物化性质

• 沸点：
  479.8±30.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-dibenzoylpyrrole 在 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 76.0h， 生成 2,7,12,17-Tetraphenyl-4,14,21,23-tetrazapentacyclo[16.2.1.13,6.18,11.113,16]tetracosa-1(20),3(24),5,8,10,13(22),15,18-octaene
  参考文献：
  名称：

  DOUBLYN-CONFUSED CALIX[4]PYRROLE PREPARED BY RATIONAL SYNTHESIS

  摘要：

  Doubly N-confused calix[4]pyrrole 4 is prepared in high yield by the [3 + 1] condensation of tripyrrane 3 with 2,4-dihdoxymethylpyrrole 2 under acid-catalysed conditions.

  DOI：

  10.1081/scc-120003153
• 作为产物：
  描述：

  3-苯甲酰吡咯 在 吡啶 、 tetrafluoroboric acid 、 mercury(II) oxide 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 7.0h， 生成 2,4-dibenzoylpyrrole
  参考文献：
  名称：

  Cadamuro, Silvano; Degani, Iacopo; Dughera, Stefano, Journal of the Chemical Society. Perkin transactions I, 1993, # 2, p. 273 - 284

  摘要：

  DOI：

文献信息

• Stepwise syntheses of core-modified, meso-substituted porphyrins
  作者：Phil-Yeon Heo、Koo Shin、Chang-Hee Lee

  DOI：10.1016/0040-4039(95)02127-2

  日期：1996.1

  e, thiophene and furan derivatives with pyrrole in the presence of acid catalyst. The core-modified porphyrins were synthesized by acid catalyzed 3 + 1 condensation of modified tripyrrins with 2,5-bis(α-hydroxymethyl)-substituted pyrrole, thiophene or furan. This new process gives a single porphyrin isomer and overcome the synthetic problems associated with separation and purification of regioisomeric

  发现在酸性催化剂存在下，通过2，5-双（α-羟甲基）吡咯，噻吩和呋喃衍生物与吡咯的缩合，可以得到简单的条件来得到改性的三吡啶衍生物。核心修饰的卟啉通过酸修饰的三联吡啶与2,5-双（α-羟甲基）取代的吡咯，噻吩或呋喃的3 + 1缩合反应合成。该新方法提供了单一的卟啉异构体，并克服了与分离和纯化区域异构体混合物相关的合成问题。
• Substituted Pyrrol-1-ylacetic Acids That Combine Aldose Reductase Enzyme Inhibitory Activity and Ability To Prevent the Nonenzymatic Irreversible Modification of Proteins from Monosaccharides
  作者：Ioannis Nicolaou、Vassilis J. Demopoulos

  DOI：10.1021/jm0209477

  日期：2003.1.1

  Starting from the known inhibitory activity of (3-benzoylpyrrol-1-yl)acetic acid (1) and (2-benzoylpyrrol-1-yl)acetic acid (II), a series of 3-aroyl and 2,4-bis-aroyl derivatives (54-75) were synthesized and tested for inhibition of aldose reductase, an enzyme involved in the appearance of diabetic complications. It was found that a number of the tested compounds exhibited considerable activity in the micromolar range. Important structural features for the potent compounds is the presence of substituents with relatively low Hammett sigma values and/ or moieties which increase their overall aromatic area. The most active derivative was the [2,4-bis(4-methoxybenzoyl)pyrrol-1-yl] acetic acid (75), with potency favorably compared to known ARIs such as tolrestat, epalrestat, zopolrestat, and fidarestat. Four selected derivatives were also evaluated for their ability to interfere with the oxidative modification of serum albumin in an in vitro experimental glycation model of diabetes mellitus. All of them showed considerable activity, comparable to the known inhibitor trolox. Our results, taken together, indicate that compound 75 combines favorably two biological activities directly connected to a number of pathological conditions related to the chronic diabetes mellitus.
• Syntheses, Structures, and Crystal Packing of N-Confused 5,20-Diphenylporphyrin and Ag(III) Complex
  作者：Hiroyuki Furuta、Tatsuki Morimoto、Atsuhiro Osuka

  DOI：10.1021/ol034172n

  日期：2003.5.1

  graphicb-Unsubstituted meso partially free N-confused porphyrin, N-confused 5,20-diphenylporphyrin (NCDPP, 3), was synthesized in 7% yield by [3 + 1] condensation reaction followed by oxidation. The structures of the free base and its Ag(III) complex were elucidated by the single-crystal X-ray analyses. The Ag(III) complex was more planar than the free base and formed columnar structures stacking to each other with a 3.3 Angstrom distance in the crystal.
• Cadamuro, Silvano; Degani, Iacopo; Dughera, Stefano, Journal of the Chemical Society. Perkin transactions I, 1993, # 2, p. 273 - 284
  作者：Cadamuro, Silvano、Degani, Iacopo、Dughera, Stefano、Fochi, Rita、Gatti, Antonella、Piscopo, Laura

  DOI：——

  日期：——
• DOUBLY<i>N</i>-CONFUSED CALIX[4]PYRROLE PREPARED BY RATIONAL SYNTHESIS
  作者：Qingqi Chen、Tianyu Wang、Yi Zhang、Qiuan Wang、Jinshi Ma

  DOI：10.1081/scc-120003153

  日期：2002.1

  Doubly N-confused calix[4]pyrrole 4 is prepared in high yield by the [3 + 1] condensation of tripyrrane 3 with 2,4-dihdoxymethylpyrrole 2 under acid-catalysed conditions.