dimethyl quinolin-2-ylphosphonate | 257637-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: dimethyl quinolin-2-ylphosphonate
• 英文别名: 2-Dimethoxyphosphorylquinoline
• CAS: 257637-46-0
• 化学式: C₁₁H₁₂NO₃P
• 分子量: 237.195
• InChiKey: XWOUBOJPHVHGIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯基锂 、 dimethyl quinolin-2-ylphosphonate 在 四甲基乙二胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以29%的产率得到2-苯基喹啉
  参考文献：
  名称：

  N-Heteroarylphosphonates, Part II. Synthesis and Reactions of 2- and 4-Phosphonatoquinolines and Related Compounds

  摘要：

  DOI：

  10.1055/s-1999-3627
• 作为产物：
  描述：

  在 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.17h， 生成 dimethyl quinolin-2-ylphosphonate
  参考文献：
  名称：

  N-Heteroarylphosphonates, Part II. Synthesis and Reactions of 2- and 4-Phosphonatoquinolines and Related Compounds

  摘要：

  DOI：

  10.1055/s-1999-3627

文献信息

• Metal-free phosphonation of heteroarene N-oxides with trialkyl phosphite at room temperature
  作者：Ming-Tao Chen、Xia You、Li-Gang Bai、Qun-Li Luo

  DOI：10.1039/c7ob00402h

  日期：——

  A new protocol is described for the conversion of heteroarene N-oxides to heteroarylphosphonates through in situ activation with bromotrichloromethane. The N-oxides of isoquinoline, quinoline, quinoxaline and 1,10-phenanthroline were fast transformed into the corresponding heteroarylphosphonates in up to 92% yield under mild conditions in the absence of solvent and metal catalysts. The good functional

  描述了用于通过用三氯甲烷原位活化将杂芳烃N-氧化物转化为杂芳基膦酸酯的新方案。在没有溶剂和金属催化剂的条件下，在温和条件下，异喹啉，喹啉，喹喔啉和1,10-菲咯啉的N-氧化物被快速转化为相应的杂芳基膦酸酯，收率高达92％。良好的官能团耐受性，低成本，扩大规模的可行性以及试剂的广泛可用性，使该方法成为平尾偶联的重要补充。
• Direct regioselective phosphonation of heteroaryl N-oxides with H-phosphonates under metal and external oxidant free conditions
  作者：Hui Wang、Xiuling Cui、Yu Pei、Qianqian Zhang、Jie Bai、Donghui Wei、Yangjie Wu

  DOI：10.1039/c4cc07060g

  日期：——

  A direct C–H/P–H functionalization of heteroaryl N-oxides with H-phosphonates under metal and oxidant free conditions was developed. Various heteroaryl phosphonate derivatives were obtained in up to 92% yield in a chemo- and regioselective manner.

  通过无金属和氧化剂的条件，开发了一种直接的杂环氧化物N-氧化物与H-膦酸酯的C-H/P-H官能化反应。以高达92%的产率以化学选择性和位置选择性的方式获得了各种杂环膦酸酯衍生物。
• Coupling Reactions of Heteroarenes with Phosphites under Silver Catalysis
  作者：Chang-Bing Xiang、Yong-Jun Bian、Xue-Rong Mao、Zhi-Zhen Huang

  DOI：10.1021/jo301108g

  日期：2012.9.7

  A silver-catalyzed dehydrogenative cross-coupling reaction of substituted furans, thiophene, thioazole, and pyrrole 1a-e with dialkyl phosphites 2 was first developed to afford corresponding phosphonated products 3a-h with up to 89% yield and good regioselectivities. Moreover, an unprecedented coupling of various substituted pyridines 1f-k with dialkyl phosphites 2 using AgNO3 as a catalyst and K2S2O8 as an oxidant, followed by reduction with Na2S2O3, was also realized to furnish desired pyridine phosphonates 3i-q in satisfactory yields with good regioselectivities.