4-甲基-alpha-咔啉 | 13174-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 4-甲基-alpha-咔啉
• 英文名称: 4-methyl-9H-pyrido[2,3-b]indole
• 英文别名: 4-methyl-6-carboline；4-methyl-9H-pyrido[2,3-b]indole；4-Methyl-9H-pyrido[2,3-b]indol；4-Methyl-α-carbolin
• CAS: 13174-97-5
• 化学式: C₁₂H₁₀N₂
• mdl: MFCD18803947
• 分子量: 182.225
• InChiKey: MIOULEPPXLEANT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-甲基-alpha-咔啉 在 三乙胺 、 sodium iodide 作用下， 以 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 34.33h， 生成 3-(9-dodecyl-1-methyl-4,9-dihydro-1H-pyrido(indol-4-yl)methyl)-4-ethoxycyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Synthesis of novel semi-squaraine derivatives and application in efficient dye-sensitized solar cells

  摘要：

  A series of novel semi-squaraine sensitizers with various architectures and anchors have been synthesized and utilized in dye-sensitized solar cells. These dyes combine indole- or carboline-based electron rich units with strongly electron-withdrawing cyanoacetate moieties or other functional anchoring moieties. They were thoroughly characterized as per their structural, optical and electrochemical properties and the behavior of the as prepared solar cells were examined in detail using linear sweep voltammetry, electrochemical impedance spectroscopy and DFT calculations. Amongst the herein reported dyes, AKSq1, incorporating a free hydroxyl group directly attached to the squarate ring, exerts the optimum performance in dye-sensitized solar cells, despite the fact that this dye presents the lowest extinction coefficient among the molecules under study. AKSq1 demonstrates power conversion efficiency of 2.63%, about 14% higher than the efficiency obtained with the corresponding reference dye, the commercially available, high-performance, metal-free dye D35, under the same cell fabrication and measuring conditions. This result is attributed to the presence of free squaryl hydroxyl moiety ensuring efficient dye chemisorption and the existence of a lipophilic dodecyl group preventing the aggregation of the squaraine sensitizer onto the semiconductor's surface either by itself, or via increased intercalation of the C12 chain with the chenodeoxycholic acid coadsorbent.

  DOI：

  10.1016/j.dyepig.2019.02.028
• 作为产物：
  描述：

  4-methyl-N-phenylpyridin-2-amine 在 palladium diacetate 、 三氟乙酸 作用下， 反应 6.0h， 以33%的产率得到4-甲基-alpha-咔啉
  参考文献：
  名称：

  Synthesis of novel semi-squaraine derivatives and application in efficient dye-sensitized solar cells

  摘要：

  A series of novel semi-squaraine sensitizers with various architectures and anchors have been synthesized and utilized in dye-sensitized solar cells. These dyes combine indole- or carboline-based electron rich units with strongly electron-withdrawing cyanoacetate moieties or other functional anchoring moieties. They were thoroughly characterized as per their structural, optical and electrochemical properties and the behavior of the as prepared solar cells were examined in detail using linear sweep voltammetry, electrochemical impedance spectroscopy and DFT calculations. Amongst the herein reported dyes, AKSq1, incorporating a free hydroxyl group directly attached to the squarate ring, exerts the optimum performance in dye-sensitized solar cells, despite the fact that this dye presents the lowest extinction coefficient among the molecules under study. AKSq1 demonstrates power conversion efficiency of 2.63%, about 14% higher than the efficiency obtained with the corresponding reference dye, the commercially available, high-performance, metal-free dye D35, under the same cell fabrication and measuring conditions. This result is attributed to the presence of free squaryl hydroxyl moiety ensuring efficient dye chemisorption and the existence of a lipophilic dodecyl group preventing the aggregation of the squaraine sensitizer onto the semiconductor's surface either by itself, or via increased intercalation of the C12 chain with the chenodeoxycholic acid coadsorbent.

  DOI：

  10.1016/j.dyepig.2019.02.028

文献信息

• Synthesis of some substituted α-carbolines
  作者：L. Stephenson、W. K. Warburton

  DOI：10.1039/j39700001355

  日期：——

  salt is converted by alkali into the anhydronium base (III; R = OMe). The salt (II; R = H) and the base (III; R = OMe) are converted by sufficiently basic nucleophilic reagents into 2-substituted α-carbolines; the salt (II; R = Me) reacts even more readily with basic nucleophilic compounds.

  α-Carboline-1-oxide（I）与乙酸酐得到2-乙酰氧基-9-乙酰基-α-咔啉；用硫酸二甲酯得到盐（Ⅱ； R ＝ H）。后者的盐通过碱转化为an鎓碱（III； R = OMe）。盐（Ⅱ； R = H）和碱（Ⅲ； R = OMe）通过足够碱性的亲核试剂转化为2-取代的α-咔啉；盐（II; R = Me）与碱性亲核化合物反应更容易。
• A New Route to α-Carbolines Based on 6π-Electrocyclization of Indole-3-alkenyl Oximes
  作者：Sophie J. Markey、William Lewis、Christopher J. Moody

  DOI：10.1021/ol403191k

  日期：2013.12.20

  Indoles are converted into alpha-carbolines in four steps by acylation at C-3, Boc-protection, olefination of the resulting 3-indolylaldehydes or ketones to give N-Boc-3-indolyl alkenyl oxime O-methyl ethers, which upon heating to 240 degrees C under microwave irradiation undergo loss of the Boc-group, and 6 pi-electrocyclization to alpha-carbolines, following aromatization by loss of methanol (11 examples, 30-90% yield).
• Synthesis of Carbolines by Photostimulated Cyclization of Anilinohalopyridines
  作者：Joydev K. Laha、Silvia M. Barolo、Roberto A. Rossi、Gregory D. Cuny

  DOI：10.1021/jo200923n

  日期：2011.8.5

  A general synthetic route to prepare all four carboline regioisomers by photo stimulated cyclization of anilinohalopyridines is described. The methodology affords various substituted carbolines in good to excellent yields. In the case of alpha-carbolines, the S(RN)1 methodology complements previously reported palladium-catalyzed cyclization approaches.
• 3-carboline derivatives
  申请人：SEARLE & CO

  公开号：US02690441A1

  公开（公告）日：1954-09-28
• 1-aminoalkyl-3-carbolines
  申请人：SEARLE & CO

  公开号：US02688022A1

  公开（公告）日：1954-08-31