diethyl 1-(6-methoxy-2-naphthyl)ethylphosphonate | 220262-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl 1-(6-methoxy-2-naphthyl)ethylphosphonate
• 英文别名: 2-(1-Diethoxyphosphorylethyl)-6-methoxynaphthalene
• CAS: 220262-63-5
• 化学式: C₁₇H₂₃O₄P
• 分子量: 322.341
• InChiKey: AUGIRDCOTGPZPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 1-(6-methoxy-2-naphthyl)ethylphosphonate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以80%的产率得到ethyl hydrogen ((S)-1-(6-methoxynaphthalen-2-yl)ethyl)phosphonate
  参考文献：
  名称：

  路易斯酸使酮磷酸化成为可能：烯基膦酸酯的合成

  摘要：

  已经开发出一种有效的路易斯酸使酮膦酰化以合成乙烯基膦酸酯。该方法依赖于酮氢膦酰化/α-羟基膦酸酯单分子消除 (E1) 脱水级联反应序列。以中等至极好的收率获得了各种CP键形成产物，水作为反应中唯一的副产物。

  DOI：

  10.1002/cjoc.202100083
• 作为产物：
  描述：

  2-(溴甲基)-6-甲氧基萘 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 diethyl 1-(6-methoxy-2-naphthyl)ethylphosphonate
  参考文献：
  名称：

  单克隆抗体催化萘普生乙酯的对映选择性水解。

  摘要：

  该报告描述了从易于获得的2-乙酰基-6-甲氧基萘5中成功合成了模仿萘普生乙酯水解过渡态的外消旋膦酸酯3的半抗原。然后免疫BALB / C小鼠，一只给出了对映选择性地加速R-（-）-萘普生乙酯水解的单克隆催化抗体N116-27。催化反应的Michaelis-Menton参数为K（M）= 6.67 mM和k（cat）/ k（uncat）= 5.8 x 10（4）。该对映选择性的结果是由于rac-半抗原的R-异构体比S-异构体具有更高的免疫原性这一事实所解释。

  DOI：

  10.1016/s0968-0896(02)00074-3

文献信息

• Metal-free diimide reduction of alkenylphosphonates: simple and efficient protocol for the synthesis of α-substituted ethylphosphonates
  作者：Yewen Fang、Meijuan Yuan、Xiaoping Jin、Li Zhang、Ruifeng Li、Shaoshuai Yang、Mei Fang

  DOI：10.1016/j.tetlet.2016.02.057

  日期：2016.3

  A simple and straightforward method for the synthesis of α-substituted ethylphosphonates via diimide reduction strategy is described. With K3PO4 or Na2CO3 as the basic additive, a range of terminal alkenylphosphonates underwent efficient reduction by diimide generated from 2-nitrobenzenesulfonylhydrazide (NBSH) under room temperature. The high functional group tolerance of this methodology is also

  描述了一种通过二酰亚胺还原策略合成α-取代的乙基膦酸酯的简单直接的方法。以K 3 PO 4或Na 2 CO 3为基本添加剂，在室温下，一定范围内的末端链烯基膦酸酯被2-硝基苯磺酰肼（NBSH）生成的二酰亚胺有效还原。还证明了该方法具有较高的官能团耐受性。此外，我们的方法具有安全性高，反应条件温和，对设备的要求低以及化学选择性高的特点。
• A practical synthetic approach to chiral α-aryl substituted ethylphosphonates
  作者：Natalia S Goulioukina、Tat'yana M Dolgina、Irina P Beletskaya、Jean-Christophe Henry、Damien Lavergne、Virginie Ratovelomanana-Vidal、Jean-Pierre Genet

  DOI：10.1016/s0957-4166(01)00031-3

  日期：2001.2

  A convenient general method is reported for the synthesis of α-aryl substituted ethylphosphonic acids and esters by hydrogenation of α-aryl substituted ethenylphosphonic acids and esters. Racemic α-arylethylphosphonic acids and esters were prepared in 70–88% yield under palladium-assisted transfer hydrogenation conditions using ammonium formate. Asymmetric hydrogenation of α-arylethenylphosphonic acids

  已经报道了一种通过氢化α-芳基取代的乙烯基膦酸和酯来合成α-芳基取代的乙基膦酸和酯的常规方法。外消旋α-芳基乙基膦酸和酯是在甲酸辅助下，在钯辅助转移氢化条件下以70-88％的收率制备的。使用手性Ru（II）催化剂对α-芳基乙烯基膦酸进行不对称加氢可生成对映体过量高达86％的α-芳基乙基膦酸。
• Enantioselective Synthesis of Chiral α-Aryl or α-Alkyl Substituted Ethylphosphonates via Rh-Catalyzed Asymmetric Hydrogenation with a <i>P</i>-Stereogenic BoPhoz-Type Ligand
  作者：Dao-Yong Wang、Xiang-Ping Hu、Jun Deng、Sai-Bo Yu、Zheng-Chao Duan、Zhuo Zheng

  DOI：10.1021/jo900417m

  日期：2009.6.5

  An enantioselective synthesis of optically active 1-aryl or 1-alkyl substituted ethylphosphonates, based on the first Rh-catalyzed asymmetric hydrogenation of corresponding alpha,beta-unsaturated precursors with a P-stereogenic BoPhoz-type ligand under the mild condition, was developed, in which a wide range of 1-aryl or 1-alkyl substituted ethylphosphonates were achieved in up to 98% ee.
• Cheruku, Pradeep; Paptchikhine, Alexander; Church, Tamara L., Journal of the American Chemical Society, 2009, vol. 131, p. 8285 - 8289
  作者：Cheruku, Pradeep、Paptchikhine, Alexander、Church, Tamara L.、Andersson, Pher G.

  DOI：——

  日期：——
• ——
  作者：N. S. Gulyukina、T. M. Dolgina、G. N. Bondarenko、I. P. Beletskaya、N. A. Bondarenko、J. -C. Henry、D. Lavergne、V. Ratovelomanana-Vidal、J. -P. Genet

  DOI：10.1023/a:1016511609369

  日期：——

  A convenient and inexpensive general preparation method for 1-arylethylphosphonic acids and their esters was developed involving in reduction of the corresponding 1-ethenylphosphonates by ammonium formate in the presence of palladium on carbon. A homogeneous enantioselective hydrogenation of 1-arylethenylphosphonic acids in the presence of chiral ruthenium catalysts provided optically active 1-arylethylphosphonic acids of enantiomeric purity up to 86%. The preliminary data on biological activity testing of the 1-arylethylphosphoic acids synthesized evidence that some among the compounds obtained are low-toxic substances with the properties of immunosuppressors of the central type of action.