diisopropyl 1H-indol-1-ylphosphonate | 1417780-54-1

• 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: diisopropyl 1H-indol-1-ylphosphonate
• 英文别名: 1-[Oxido-di(propan-2-yloxy)phosphaniumyl]indole；1-[oxido-di(propan-2-yloxy)phosphaniumyl]indole
• CAS: 1417780-54-1
• 化学式: C₁₄H₂₀NO₃P
• 分子量: 281.291
• InChiKey: HZRXZOURXAEUDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吲哚 、 亚磷酸二异丙酯 在 4-甲基吡啶 、 copper diacetate 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 0.67h， 以53%的产率得到diisopropyl 1H-indol-1-ylphosphonate
  参考文献：
  名称：

  Copper-Catalyzed Oxidative Cross-Coupling of H-Phosphonates and Amides to N-Acylphosphoramidates

  摘要：

  A simple combination of copper(II) acetate (Cu(OAc)(2)) and an appropriate base could promote oxidative cross-coupling of H-phosphonates and amides using air as a terminal oxidant. The substrate scope was broad with respect to both dialkyl H-phosphonates and nitrogen nucleophiles (including oxazolidinone, lactam, pyrrolidinone, urea, indole, and sulfonamide derivatives), giving the corresponding P-N coupling products in moderate to high yields.

  DOI：

  10.1021/ol303420g

文献信息

• 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。
• Copper-Catalyzed Oxidative Cross-Coupling of <i>H</i>-Phosphonates and Amides to <i>N</i>-Acylphosphoramidates
  作者：Xiongjie Jin、Kazuya Yamaguchi、Noritaka Mizuno

  DOI：10.1021/ol303420g

  日期：2013.1.18

  A simple combination of copper(II) acetate (Cu(OAc)(2)) and an appropriate base could promote oxidative cross-coupling of H-phosphonates and amides using air as a terminal oxidant. The substrate scope was broad with respect to both dialkyl H-phosphonates and nitrogen nucleophiles (including oxazolidinone, lactam, pyrrolidinone, urea, indole, and sulfonamide derivatives), giving the corresponding P-N coupling products in moderate to high yields.