1-phenethyl-1H-pyrrole-2-carbaldehyde | 49795-42-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-phenethyl-1H-pyrrole-2-carbaldehyde
• 英文别名: 1-(2-phenylethyl)-2-formylpyrrole；1-phenethyl-pyrrole-2-carbaldehyde；1-(2-Phenylaethyl)-2-formylpyrrol；1-(2-Phenylethyl)pyrrol；1-(2-Phenylethyl)-2-formylpyrrol；1-(2-phenylethyl)pyrrole-2-carbaldehyde
• CAS: 49795-42-8
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: ITWVWJWDKXWQFS-UHFFFAOYSA-N

物化性质

• 沸点：
  350.9±25.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)
• 保留指数：
  2557

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenethyl-1H-pyrrole-2-carbaldehyde 在 sodium hydride 、 对苯二酚 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 68.0h， 生成 1-Phenethyl-1H-indole-4,7-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  A three-residue, continuous binding epitope peptidomimetic of ShK toxin as a Kv1.3 inhibitor

  摘要：

  The ShK toxin is a polypeptide that blocks the Kv1.3 potassium channel in T-lymphocytes and has been identified as a potential therapeutic for multiple sclerosis. ShK is well characterised in terms of structure and binding, offering an attractive target for the design of structural and functional mirnetics. Building on our previous success in developing rationally designed peptidomimetics of ShK, we report a novel mimetic of the K22 Y23-R24 residues of the peptide. The mimetic was shown to inhibit the Kv1.3 channel with moderate activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.014
• 作为产物：
  描述：

  2-吡咯甲醛 、 乙基溴苯 在 四丁基溴化铵 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以76%的产率得到1-phenethyl-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  A three-residue, continuous binding epitope peptidomimetic of ShK toxin as a Kv1.3 inhibitor

  摘要：

  The ShK toxin is a polypeptide that blocks the Kv1.3 potassium channel in T-lymphocytes and has been identified as a potential therapeutic for multiple sclerosis. ShK is well characterised in terms of structure and binding, offering an attractive target for the design of structural and functional mirnetics. Building on our previous success in developing rationally designed peptidomimetics of ShK, we report a novel mimetic of the K22 Y23-R24 residues of the peptide. The mimetic was shown to inhibit the Kv1.3 channel with moderate activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.014

文献信息

• Selective and Efficient Formylation of Indoles (C3) and Pyrroles (C2) Using 2,4,6-Trichloro-1,3,5-Triazine/Dimethylformamide (TCT/DMF) Mixed Reagent
  作者：Nasser Iranpoor、Farhad Panahi、Soodabeh Erfan、Fatemeh Roozbin

  DOI：10.1002/jhet.2652

  日期：2017.3

  one equivalent of 2,4,6‐trichloro‐1,3,5‐triazine (cyanuric chloride) generates an easy handling formylating agent for the efficient formylation of these classes of compounds to give the corresponding aldehydes under mild reaction conditions. This procedure was highly efficient, and a range of formylated indoles and pyrroles were obtained in good to excellent yields.

  这项研究介绍了一种有效的方法，分别在C（3）和C（2）的位置对吲哚和吡咯进行选择性甲酰化。三当量的N，N-二甲基甲酰胺和一当量的2,4,6-三氯-1,3,5-三嗪（氰尿酰氯）的混合物可生成易于处理的甲酰化剂，以有效地将此类化合物甲酰化为在温和的反应条件下得到相应的醛。该方法是高效的，并且以良好至优异的产率获得了一系列甲酰化的吲哚和吡咯。
• Intramolecular Oxidative Arylations in 7-Azaindoles and Pyrroles: Revamping the Synthesis of Fused <i>N</i> -Heterocycle Tethered Fluorenes
  作者：Joydev K. Laha、Rohan A. Bhimpuria、Mandeep Kaur Hunjan

  DOI：10.1002/chem.201604192

  日期：2017.2.10

  and pyrroles that, for the first time, provided direct access to 7‐azaindole‐ or pyrrole‐fused isoindolines and tetrahydroisoquinolines. In addition, N‐benzylation of 7‐azaindoles or pyrroles with sterically hindered sec‐benzyl alcohols by Mitsunobu reaction followed by intramolecular oxidative arylation allowed access to chiral congeners of fused isoindolines that have little precedence. A new opportunity

  我们揭示了7-氮杂吲哚和吡咯中的分子内氧化芳基化作用，这首次提供了直接接触7-氮杂吲哚或吡咯融合的异吲哚啉和四氢异喹啉的途径。此外，通过Mitsunobu反应将7-氮杂吲哚或吡咯与位阻仲仲苄醇进行N-苄基化反应，然后进行分子内氧化芳基化反应，可以使融合异二氢吲哚的手性同类物获得优先利用。芴基有机发射体的设计和合成中的新机会在制备新型的稠合N杂环拴式芴（包括手性芴结构）中得到了证明。
• A three-residue, continuous binding epitope peptidomimetic of ShK toxin as a Kv1.3 inhibitor
  作者：Andrew J. Harvey、Robert W. Gable、Jonathan B. Baell

  DOI：10.1016/j.bmcl.2005.05.014

  日期：2005.7

  The ShK toxin is a polypeptide that blocks the Kv1.3 potassium channel in T-lymphocytes and has been identified as a potential therapeutic for multiple sclerosis. ShK is well characterised in terms of structure and binding, offering an attractive target for the design of structural and functional mirnetics. Building on our previous success in developing rationally designed peptidomimetics of ShK, we report a novel mimetic of the K22 Y23-R24 residues of the peptide. The mimetic was shown to inhibit the Kv1.3 channel with moderate activity. (c) 2005 Elsevier Ltd. All rights reserved.