diethyl (3-methyl-1H-indol-2-yl)phosphonate | 59823-26-6

• 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
• 英文名称: diethyl (3-methyl-1H-indol-2-yl)phosphonate
• 英文别名: methyl-3 indole-2 phosphonate de diethyle；Diethyl 3-methyl-1h-indol-2-ylphosphonate；2-diethoxyphosphoryl-3-methyl-1H-indole
• CAS: 59823-26-6
• 化学式: C₁₃H₁₈NO₃P
• 分子量: 267.265
• InChiKey: NANOFWFDDNNWQR-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  410.4±33.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  anilino-1 oxo-2 propylphosphonate de diethyle 在 zinc(II) chloride 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以10%的产率得到diethyl (3-methyl-1H-indol-2-yl)phosphonate
  参考文献：
  名称：

  Haelters, J. P.; Corbel, B.; Sturtz, G., Phosphorus and Sulfur and the Related Elements, 1988, vol. 37, p. 65 - 86

  摘要：

  DOI：

文献信息

• Electrochemical oxidative phosphorylation of azoles in the presence of silver catalysts
  作者：E. O. Yurko、T. V. Gryaznova、V. V. Khrizanforova、M. N. Khrizanforov、A. V. Toropchina、Yu. H. Budnikova、O. G. Sinyashin

  DOI：10.1007/s11172-018-2043-5

  日期：2018.1

  phosphorylation of benzo-1,3-azoles (benzoxazole, benzothiazole, and 3-methylindole) with diethyl phosphite by electrocatalytic oxidation was proposed. The process occurs under electrochemical mild conditions (room temperature, normal pressure) in the presence of silver salts or silver oxide. This method allows one to obtain 2-phosphorylated products of benzo-1,3-azoles in good yield (up to 75%).

  提出了一种通过电催化氧化用亚磷酸二乙酯磷酸化苯并 1,3-唑类（苯并恶唑、苯并噻唑和 3-甲基吲哚）的新方法。该过程在银盐或氧化银存在下在电化学温和条件（室温、常压）下进行。该方法允许以良好的产率（高达 75%）获得苯并-1,3-唑类的 2-磷酸化产物。
• Direct C−H Phosphonylation of Electron-Rich Arenes and Heteroarenes by Visible-Light Photoredox Catalysis
  作者：Rizwan S. Shaikh、Indrajit Ghosh、Burkhard König

  DOI：10.1002/chem.201701283

  日期：2017.9.7

  the atom economy and allows preparing and modifying complex molecules more easily. . In contrast to the wide applications of aryl phosphonates, their synthesis via direct C-H bond phosphonylation is a less explored area. We report here a general, mild, and broadly applicable visible light photoredox C-H bond phosphonylation method for electron rich arenes and heteroarenes. The photoredox catalytic protocol

  普遍存在的但化学惰性的CH键直接转化为各种官能团是有机合成中的重要策略，可提高原子经济性并允许更轻松地制备和修饰复杂分子。。与芳基膦酸酯的广泛应用相反，其通过直接CH键膦酰化的合成是探索较少的领域。我们在此报告了一种适用于富电子芳烃和杂芳烃的通用，温和且广泛适用的可见光光氧化还原CH键膦酰化方法。光氧化还原催化方案利用富电子的芳烃和生物学上重要的杂芳烃作为底物，[Ru（bpz）3] [PF 6] 2作为光催化剂，过硫酸铵作为氧化剂，
• Electrochemical Regioselective Phosphorylation of Nitrogen‐Containing Heterocycles and Related Derivatives
  作者：Yong Deng、Shiqi You、Mengyao Ruan、Ying Wang、Zuxing Chen、Guichun Yang、Meng Gao

  DOI：10.1002/adsc.202000997

  日期：2021.1.19

  The site‐selective functionalization of biologically important nitrogen‐containing heterocycles and related derivatives remains a challenging and important task. We report herein on the direct regiodivergent N1/C2 phosphorylation of free indole derivatives. Cyclic voltammograms and EPR data indicate that by utilizing different electrolyte‐mediated anodic oxidation to generate different active indole

  对生物学上重要的含氮杂环和相关衍生物的位点选择性官能化仍然是一项艰巨而重要的任务。我们在这里报道了游离吲哚衍生物的直接区域发散性的N1 / C2磷酸化。循环伏安图和EPR数据表明，通过利用不同的电解质介导的阳极氧化生成不同的活性吲哚物种，在无外源氧化剂和金属催化剂的情况下，可以中等至高收率获得各种N1和C2磷酸化产物。游离电化学条件。另外，还发现NP偶联与各种烷基胺相容。
• Direct Oxidative C-P Bond Formation of Indoles with Dialkyl Phosphites
  作者：Boshun Wan、Haolong Wang、Xincheng Li、Fan Wu

  DOI：10.1055/s-0031-1289700

  日期：2012.3

  The direct phosphonation of indoles was developed. In this reaction, dialkyl phosphites and indoles were used as substrates, and the C-P bond was formed through oxidative coupling mediated by silver(I) acetate. Various indoles and different dialkyl phosphites were effective substrates for the reaction, and dialkylphosphoryl-substituted indoles were obtained in up to 71% yield.

  开发了吲哚的直接膦化反应。该反应以二烷基膦酸盐和吲哚为底物，通过醋酸银（I）介导的氧化偶联形成 C-P 键。各种吲哚和不同的二烷基膦酸盐都是该反应的有效底物，得到的二烷基膦酸盐取代吲哚的产率高达 71%。
• An expedient synthesis of pyrrole-2-phosphonates via direct oxidative phosphorylation and γ-hydroxy-γ-butyrolactams from pyrroles
  作者：Se Hee Kim、Ko Hoon Kim、Jin Woo Lim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2013.11.082

  日期：2014.1

  An expedient oxidative phosphorylation of pyrroles has been disclosed. The reaction of dialkyl phosphite and pyrrole in the presence of AgNO3/K2S2O8 in DMF/H2O (8:1) produced pyrrole-2-phosphonates in good yields. In the absence of dialkyl phosphite, gamma-hydroxy-gamma-butyrolactam derivative was formed as a major product. (C) 2013 Elsevier Ltd. All rights reserved.