[2-(N-acetyl)aminophenyl]phosphonic acid diethyl ester | 42822-64-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [2-(N-acetyl)aminophenyl]phosphonic acid diethyl ester
• 英文别名: 2-acetamido-benzenephosphonic acid diethylester；2-acetamidobenzenephosphonic acid diethyl ester；diethyl [2-(acetamido)phenyl]phosphonate；diethyl (2-acetamidophenyl)phosphonate；diethyl 2-acetamidophenylphosphonate；Diethyl-2-acetamidophenylphosphonat；N-(2-diethoxyphosphorylphenyl)acetamide
• CAS: 42822-64-0
• 化学式: C₁₂H₁₈NO₄P
• 分子量: 271.253
• InChiKey: HKYCMRNXORFRIE-UHFFFAOYSA-N

物化性质

• 沸点：
  426.8±28.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [2-(N-acetyl)aminophenyl]phosphonic acid diethyl ester 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以54%的产率得到[2-(N-acetyl)aminophenyl]phosphonic acid monoethyl ester
  参考文献：
  名称：

  Intramolecular Hydrogen-Bond Participation in Phosphonylammonium Salt Formation

  摘要：

  A series of phosphonochloridates and phosphonyl dichlorides were prepared, and their reactivity with triethylamine has been investigated using P-31 NMR spectroscopy, Taken together these studies provide evidence that an intramolecular hydrogen-bond is required for phosphonylammonium salt formation to render the phosphorus more electron-deficient.

  DOI：

  10.1021/ol0066330
• 作为产物：
  描述：

  ortho-nitro-phenylphosphonate diethylique 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 [2-(N-acetyl)aminophenyl]phosphonic acid diethyl ester
  参考文献：
  名称：

  Intramolecular Hydrogen-Bond Participation in Phosphonylammonium Salt Formation

  摘要：

  A series of phosphonochloridates and phosphonyl dichlorides were prepared, and their reactivity with triethylamine has been investigated using P-31 NMR spectroscopy, Taken together these studies provide evidence that an intramolecular hydrogen-bond is required for phosphonylammonium salt formation to render the phosphorus more electron-deficient.

  DOI：

  10.1021/ol0066330

文献信息

• Pd(II)-Catalyzed Phosphorylation of Aryl C–H Bonds
  作者：Chen-Guo Feng、Mengchun Ye、Kai-Jiong Xiao、Suhua Li、Jin-Quan Yu

  DOI：10.1021/ja404526x

  日期：2013.6.26

  A Pd(II)-catalyzed C-H phosphorylation reaction has been developed using heterocycle-directed ortho-palladation. Both H-phosphonates and diaryl phosphine oxides are suitable coupling partners for this reaction.

  已使用杂环定向邻位钯化开发了 Pd(II) 催化的 CH 磷酸化反应。H-膦酸酯和二芳基氧化膦都是该反应的合适偶联伙伴。
• Silver-Catalyzed Highly Regioselective Phosphonation of Arenes Bearing Electron-Withdrawing Groups
  作者：Xuerong Mao、Xiao Ma、Shuwei Zhang、Hongwen Hu、Chengjian Zhu、Yixiang Cheng

  DOI：10.1002/ejoc.201300545

  日期：2013.7

  A highly efficient, AgI/K2S2O8-mediated regioselective phosphonation reaction has been developed by using electron-deficient directing groups. These phosphonation reactions were performed with N,N-dialkylbenzamides, N,N-dialkylbenzenesulfonamides, and nitrobenzene. This method has a broad substrate scope and offers facile construction of C–P bonds.

  通过使用缺电子导向基团开发了一种高效的、AgI/K2S2O8 介导的区域选择性磷酸化反应。这些膦化反应是用 N,N-二烷基苯甲酰胺、N,N-二烷基苯磺酰胺和硝基苯进行的。这种方法具有广泛的底物范围，并且可以轻松构建 C-P 键。
• 1H-1,3-Benzazaphospholes: The Organometallic Route and a New Three-Step Synthesis with Reductive Ring Closure
  作者：Raj K. Bansal、Neelima Gupta、Joachim Heinicke、George N. Nikonov、Farida Saguitova、Dinesh C. Sharma

  DOI：10.1055/s-1999-3394

  日期：1999.2

  Primary and N-secondary 2-phosphanylanilines were synthesized via metallation of 2-bromoanilines, coupling with ClP(NMe2)2, alcoholysis and reduction with LiAlH4, and subsequently reacted with formimidoester hydrochloride to give 1,3-benzazaphospholes. For 1H-1,3-benzazaphospholes, a shorter alternative three-step synthesis was developed, based on N-acylation of 2-bromoaniline, NiCl2-catalyzed arylation of triethyl phosphite and a new reductive cyclization of amidophosphonic acid este with excess LiAlH4.

  主要和N-次级2-磷胺基苯胺通过2-溴苯胺的金属化反应、与ClP(NMe2)2偶联、醇解以及用LiAlH4还原合成，并随后与甲酰亚胺酯盐酸盐反应生成1,3-苯并氮杂膦。对于1H-1,3-苯并氮杂膦，开发了一种更短的替代三步合成方法，基于2-溴苯胺的N-酰化、NiCl2催化的三乙基磷酸酯芳基化，以及用过量LiAlH4进行的新型还原环化反应。
• Manganese-Catalyzed and Mediated Synthesis of Arylphosphinates and Related Compounds
  作者：Olivier Berger、Jean-Luc Montchamp

  DOI：10.1021/acs.joc.9b01239

  日期：2019.7.19

  H-phosphinates and related compounds was examined. A practical catalytic process with the air as the oxidant could not be found. However, an inexpensive and robust methodology was developed, using catalytic Mn(II) as the radical initiator and excess Mn(IV) as the stoichiometric oxidant. Using these conditions, the inter- and intramolecular arylation of phosphinylidene compounds has a broad scope, including

  检查了H-次膦酸酯和相关化合物的自由基芳基化。找不到以空气为氧化剂的实际催化方法。但是，开发了一种廉价而稳健的方法，使用了催化性的Mn（II）作为自由基引发剂，而过量的Mn（IV）作为化学计量的氧化剂。使用这些条件，次膦基化合物的分子间和分子内芳基化具有广泛的范围，包括应用于合成P-杂环。完整介绍了该方法，并讨论了其局限性。
• Design and Synthesis of Small Molecule Glycerol 3-Phosphate Acyltransferase Inhibitors
  作者：Edward A. Wydysh、Susan M. Medghalchi、Aravinda Vadlamudi、Craig A. Townsend

  DOI：10.1021/jm900251a

  日期：2009.5.28

  mass is growing rapidly, particularly in the United States. Glycerol 3-phosphate acyltransferase (GPAT) catalyzes the rate-limiting step of glycerolipid biosynthesis, the acylation of glycerol 3-phosphate with saturated long-chain acyl-CoAs. In an effort to produce small molecule inhibitors of this enzyme, a series of benzoic and phosphonic acids was designed and synthesized. In vitro testing of this series

  肥胖症和其他与甘油三酯含量增加相关的疾病的发病率正在迅速增长，尤其是在美国。甘油 3-磷酸酰基转移酶 (GPAT) 催化甘油脂生物合成的限速步骤，即甘油 3-磷酸与饱和长链酰基辅酶 A 的酰化。为了生产这种酶的小分子抑制剂，设计并合成了一系列苯甲酸和膦酸。该系列的体外测试导致鉴定了几种化合物，特别是 2-(壬基磺酰胺基)苯甲酸 ( 15g )，在完整线粒体分析中具有中等 GPAT 抑制活性。