diethyl(phenylcarbamoyl)phosphonate | 78759-16-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl(phenylcarbamoyl)phosphonate
• 英文别名: 1-diethoxyphosphoryl-N-phenylformamide
• CAS: 78759-16-7
• 化学式: C₁₁H₁₆NO₄P
• 分子量: 257.226
• InChiKey: LQQIBOJKLYZMKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  144-160 °C(Press: 1 Torr)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯甲酰膦酸二乙酯 以9%的产率得到
  参考文献：
  名称：

  Sprecher Milon, Kost Daniel, J. Amer. Chem. Soc, 116 (1994) N 3, S 1016-1026

  摘要：

  DOI：

文献信息

• Synthesis of organophosphorus compounds via silyl esters of phosphorous acids
  作者：Kamyar Afarinkia、Charles W. Rees、John I.G. Cadogan

  DOI：10.1016/s0040-4020(01)87899-6

  日期：1990.1

  The addition of trimethylsilyloxy phosphorus (III)derivatives generated in situ to imines at room temperature provides a mild selective and high yielding route to α-aminoalkylphosphorate and α-aminoalkylphenylphosphinate esters. Isocyanates and carbodiimides react similarly to give phosphonoureas and phosphonoguarnidines respectively aldehydes and ketones are much less reactive and cyanides are inert

  在室温下将原位产生的三甲基甲硅烷氧基磷（III）衍生物加到亚胺上，为α-氨基烷基磷酸酯和α-氨基烷基苯基次膦酸酯提供了温和的选择性和高产率的途径。异氰酸酯和碳二亚胺类似地反应，分别得到膦酰脲和膦酰胍，醛和酮的反应性低得多，氰化物是惰性的。
• Iodine-Promoted Rapid Construction of Carbamoylphosphonates from Phosphinecarboxamides
  作者：Yong-Hui Wu、Qiu-Li Wu、Wen-Peng Wang、Xi-Cun Wang、Zheng-Jun Quan

  DOI：10.1002/adsc.201800303

  日期：2018.6.15

  one‐step, I2‐promoted P−H phosphorylation and oxygenation of phosphinecarboxamides to give carbamoylphosphonates was achieved. This transformation exhibits exceptional substrate generality and functional group compatibility and affords good to excellent yields of the desired phosphonates. Notably, cyclic carbamoylphosphonates can be obtained from diols. The mechanism was investigated using IR, 1H and 31P

  一步实现了I 2促进膦膦酰胺的P-H磷酸化和氧合，生成氨基甲酰基膦酸酯。该转化表现出优异的底物通用性和官能团相容性，并提供所需膦酸酯的良好至优异的产率。值得注意的是，环状氨基甲酰基膦酸酯可以从二醇获得。使用IR，1 H和31 P NMR光谱研究了该机理。
• A novel and convenient method for synthesis of carbamoyl and thiocarbamoyl phosphonates
  作者：Babak Kaboudin、Hazegh Zahedi

  DOI：10.1002/hc.20538

  日期：——

  A simple, efficient, and general method has been developed for the synthesis of carbamoyl and thiocarbamoyl phosphonic esters using CaCl2 as an efficient Lewis base catalyst. Carbamoyl and thiocarbamoyl phosphonic esters were obtained in good yield (37%–65%) and purity under mild conditions by the reaction of diethyl phosphite with isocyanates and isothiocyanates in the presence of CaCl2. This method

  已经开发了一种简单、有效和通用的方法，用于使用 CaCl2 作为有效的路易斯碱催化剂合成氨基甲酰基和硫代氨基甲酰基膦酸酯。通过亚磷酸二乙酯与异氰酸酯和异硫氰酸酯在 CaCl2 存在下的反应，在温和条件下以良好的产率 (37%–65%) 和纯度获得氨基甲酰基和硫代氨基甲酰基膦酸酯。该方法反应简单、快速、产率好，用于合成氨基甲酰基和硫代氨基甲酰基膦酸酯。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:250–253, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20538
• Synthesis of Carbamoylphosphates from Isocyanates Catalyzed by Rare-Earth-Metal Alkyl Complexes with a Silicon-Linked Diarylamido Ligand
  作者：Xiancui Zhu、Dianjun Guo、Yiwei Zhang、Yun Wei、Shuangliu Zhou、Mengchen Xu、Shaowu Wang、Yuanqing Yang、Yawen Qi

  DOI：10.1021/acs.organomet.0c00627

  日期：2020.12.28

  Neutral rare-earth-metal monoalkyl complexes and anionic rare-earth-metal dialkyl complexes with a silicon-linked diarylamido ligand were synthesized and characterized, and their catalytic activities toward the additions of dialkyl phosphites to isocyanates were developed. Reactions of rare-earth-metal trialkyl complexes RE(CH2SiMe3)3(THF)2 with a silicon-linked diarylamine ligand in n-hexane afforded

  合成和表征了具有硅连接的二芳基酰胺配体的中性稀土金属单烷基络合物和阴离子稀土金属二烷基络合物，并开发了它们对亚磷酸二烷基酯加至异氰酸酯的催化活性。稀土类金属的反应的三烷基络合物RE（CH 2森达3）3（THF）2在硅联二芳基胺配体Ñ己烷，得到中性稀土类金属单烷基络合物大号RE（CH 2森达3） （THF）2（RE = Y（1），Er（2）; L =（Me 2Si）（2,6- i Pr 2 C 6 H 3 N）2）的产率很高。通过H 2 L，n BuLi，的盐复分解反应合成了双核稀土金属氯化物[ L RE（μ- Cl）（THF）2 ] 2（RE = Y（3），Er（4））。和无水RECl 3。用4当量的LiCH 2 SiMe 3在甲苯中处理稀土金属氯化物，生成相应的离散的异双金属稀土金属二烷基络合物L RE（CH2 SiMe 3）2（THF）Li（THF）4（RE = Y（5），Er（6））。进一步的研究表明，在存在0
• The Schmidt Reaction of Dialkyl Acylphosphonates
  作者：Milon Sprecher、Daniel Kost

  DOI：10.1021/ja00082a024

  日期：1994.2

  The scope of the Schmidt rearrangement of ketones has been extended to dialkyl acylphosphonates (11a-111). Surprisingly, it was found that 11a-11dand 11g, in which the acyl moiety was benzoyl alone or benzoyl bearing an electron-attracting or mildly electron-releasing substituent, yielded an overwhelming portion of products resulting from C-to-N migration of the aryl group (N-arylcarbamoylphosphonates

  酮的施密特重排的范围已扩展到酰基膦酸二烷基酯 (11a-111)。令人惊讶的是，发现 11a-11d 和 11g，其中酰基部分是单独的苯甲酰基或带有吸电子或轻度放电子取代基的苯甲酰基，产生了绝大多数由芳基的 C 到 N 迁移产生的产物组（N-芳基氨基甲酰基膦酸酯，12 和 N-芳基甲酰胺，15）。相反，带有强大的电子释放对烷氧基的芳烃羰基膦酸酯产生由膦酸酯基团从 C 迁移到 N 或消除的产物（N-芳烃羰基磷酰胺二烷基酯，13 和芳烃甲腈，分别为 17）