2-(hydroxymethyl)-5-[hydroxy(p-tolyl)methyl]furane | 726171-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(hydroxymethyl)-5-[hydroxy(p-tolyl)methyl]furane
• 英文别名: 2-(hydroxymethyl)-5-[hydroxyl(p-tolyl)methyl]furan；[5-(Hydroxymethyl)furan-2-yl]-(4-methylphenyl)methanol
• CAS: 726171-82-0
• 化学式: C₁₃H₁₄O₃
• 分子量: 218.252
• InChiKey: HCKVPUKDEWWERP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  53.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(hydroxymethyl)-5-[hydroxy(p-tolyl)methyl]furane 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 三苯胂 、 三氟化硼乙醚 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 5-(4-ethynylbenzoic acid)-10,15,20-tris(ptolyl)-21-oxaporphyrin
  参考文献：
  名称：

  Effects of Core-modification on Porphyrin Sensitizers to the Efficiencies of Dye-sensitized Solar Cells

  摘要：

  AbstractTo study dye‐sensitized solar cells (DSSCs) with core‐modified porphyrins as the sensitizing dyes, three porphyrins with an ethynyl benzoic acid as an anchoring group are prepared. The properties of free‐base regular porphyrin (N4), thiaporphyrin (N3S) and oxaporphyrin (N3O) were thoroughly studied by spectroscopic methods, DFT calculations, and photovoltaic measurements. Replacing one of the porphyrinic core nitrogen atoms by oxygen or sulfur considerably changes the absorption spectra. The Soret band of the N3O and N3S observed bathochromic shifts of 3‐9 nm while the Q band reaches 700 nm to the near‐infrared region. The overall conversion efficiencies of the DSSCs based on these porphyrins are in the order N4 (3.66%) ≫ N3S (0.22%) > N3O (0.01%). The time‐correlated single photon counting observed short fluorescence lifetimes for N3O adsorbed both on TiO2 and Al2O3 which explicates the poor efficiency of DSSC using N3O as the photosensitizer.

  DOI：

  10.1002/jccs.201300525
• 作为产物：
  描述：

  糠醇 、 对甲基苯甲醛 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以42%的产率得到2-(hydroxymethyl)-5-[hydroxy(p-tolyl)methyl]furane
  参考文献：
  名称：

  N3S、N3O、N2S2、N2O2、N2SO 和 N2OS 卟啉与 Onemeso 未取代碳的合成

  摘要：

  报道了一种简单直接的 N3S、N2S2、N2O2、N2SO 和 N2OS 卟啉合成方法，以及一种合成具有一个中间未取代碳原子的 N3O 卟啉的改进方法。内消旋未取代碳原子的反应性通过进行溴化和 Heck 偶联反应来证明。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200300697

文献信息

• Synthesis of A₂B-type 22-oxacorroles bearing two different five-membered heterocycles at <i>meso</i> positions
  作者：Umasekhar Booruga、Mangalampalli Ravikanth

  DOI：10.1142/s108842461950144x

  日期：2020.1

  A series of 22-oxacorroles containing mixed substituents such as either two five-membered heterocycles and one six-membered aryl group or three five-membered heterocycles at three meso positions were synthesized by 3 + 2 oxidative coupling of appropriate 16-oxatripyrrane and meso-substituted dipyrromethane under mild acid catalyzed conditions. The identities of the 22-oxacorroles were confirmed by

  一系列含有混合取代基的 22-氧杂环，例如两个五元杂环和一个六元芳基或三个五元杂环中观位置是通过适当的 16-氧杂三吡喃和 3 + 2 氧化偶联合成的中观- 取代的二吡咯甲烷在温和的酸催化条件下。22-oxacorroles 的身份由 HR-MS 光谱中各自的分子离子峰证实，并通过详细的 1D 和 2D NMR 光谱推断其结构。核磁共振研究清楚地表明核心吡咯和呋喃质子以及内部 NH 质子的上场或下场位移取决于存在的取代基的类型中观职位。所有 22-oxacorroles 都在 410-655 nm 区域吸收，吸收带的位置取决于类型中观取代基。A 2 B oxacorroles 在 600-700 nm 区域显示出一个宽而弱的荧光带，在 0.05-0.12 范围内具有低荧光量子产率。电化学研究表明，A 2 B 型22-氧杂环戊二烯比三苯基22-氧杂环戊二烯更容易氧化，也更容易还原。因此，如光
• Synthesis of N3S, N3O, N2S2, N2O2, N2SO and N2OS Porphyrins with Onemeso-Unsubstituted Carbon
  作者：Sokkalingam Punidha、Neeraj Agarwal、Ritwik Burai、Mangalampalli Ravikanth

  DOI：10.1002/ejoc.200300697

  日期：2004.5

  A simple straightforward synthesis of N3S, N2S2, N2O2, N2SO and N2OS porphyrins and an improved method for the synthesis of an N3O porphyrin with one meso-unsubstituted carbon atom are reported from readily available precursors. The reactivity of the meso-unsubstituted carbon atom was demonstrated by carrying out bromination followed by Heck coupling reactions. (© Wiley-VCH Verlag GmbH & Co. KGaA,

  报道了一种简单直接的 N3S、N2S2、N2O2、N2SO 和 N2OS 卟啉合成方法，以及一种合成具有一个中间未取代碳原子的 N3O 卟啉的改进方法。内消旋未取代碳原子的反应性通过进行溴化和 Heck 偶联反应来证明。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Effects of Core-modification on Porphyrin Sensitizers to the Efficiencies of Dye-sensitized Solar Cells
  作者：Sandeep B. Mane、Liyang Luo、Gao-Fong Chang、Eric Wei-Guang Diau、Chen-Hsiung Hung

  DOI：10.1002/jccs.201300525

  日期：2014.5

  AbstractTo study dye‐sensitized solar cells (DSSCs) with core‐modified porphyrins as the sensitizing dyes, three porphyrins with an ethynyl benzoic acid as an anchoring group are prepared. The properties of free‐base regular porphyrin (N4), thiaporphyrin (N3S) and oxaporphyrin (N3O) were thoroughly studied by spectroscopic methods, DFT calculations, and photovoltaic measurements. Replacing one of the porphyrinic core nitrogen atoms by oxygen or sulfur considerably changes the absorption spectra. The Soret band of the N3O and N3S observed bathochromic shifts of 3‐9 nm while the Q band reaches 700 nm to the near‐infrared region. The overall conversion efficiencies of the DSSCs based on these porphyrins are in the order N4 (3.66%) ≫ N3S (0.22%) > N3O (0.01%). The time‐correlated single photon counting observed short fluorescence lifetimes for N3O adsorbed both on TiO2 and Al2O3 which explicates the poor efficiency of DSSC using N3O as the photosensitizer.