alpha-羟基-3-硝基苄基膦酸二乙酯 | 50652-91-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: alpha-羟基-3-硝基苄基膦酸二乙酯
• 英文名称: diethyl 1-hydroxy-1-(3-nitrophenyl)methylphosphonate
• 英文别名: diethyl (hydroxy(3-nitrophenyl)methyl)phosphonate；Phosphonic acid, (hydroxy(3-nitrophenyl)methyl)-, diethyl ester；diethoxyphosphoryl-(3-nitrophenyl)methanol
• CAS: 50652-91-0
• 化学式: C₁₁H₁₆NO₆P
• 分子量: 289.225
• InChiKey: XQHANJBMOMOBPM-UHFFFAOYSA-N

物化性质

• 溶解度：
  39.2 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  alpha-羟基-3-硝基苄基膦酸二乙酯 在 palladium 10% on activated carbon 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 26.0h， 生成 (3-氨基苄基)膦酸二乙酯
  参考文献：
  名称：

  Synthesis and Evaluation of Phosphorus Containing, Specific CDK9/CycT1 Inhibitors

  摘要：

  Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.

  DOI：

  10.1021/jm401742r
• 作为产物：
  描述：

  diethyl α-trimethylsilyloxy-3-nitrobenzylphosphonate 在 氨基磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到alpha-羟基-3-硝基苄基膦酸二乙酯
  参考文献：
  名称：

  A convenient and mild protocol for preparation of α –trimethylsilyloxyphosphonates using sulfamic acid and their oxidation to α – ketophosphonates in the presence of N-bromosuccinimide

  摘要：

  DOI：

  10.24820/ark.5550190.p011.603

文献信息

• Magnesium triflate [Mg(OTf)2] a highly stable, non-hygroscopic and a recyclable catalyst for the high yielding preparation of diethyl α-trimethylsilyloxyphosphonates from diethyl α-hydroxyphosphonates by HMDS under solventless conditions
  作者：Habib Firouzabadi、Nasser Iranpoor、Sara Sobhani、Soheila Ghassamipour

  DOI：10.1016/j.jorganchem.2004.07.009

  日期：2004.9

  and convenient procedure for the easy conversion of various α-hydroxyphosphonates to α-trimethylsilyloxyphosphonates under mild conditions with HMDS in the presence of a catalytic amount of magnesium triflate as a highly stable and a non-hygroscopic recyclable catalyst in neat conditions is described. In order to show the general applicability of this method, we have also applied this procedure successfully

  在催化量的三氟甲磺酸镁作为高稳定性和非吸湿性可回收催化剂的条件下，使用HMDS在温和条件下将各种α-羟基膦酸酯轻松转化为α-三甲基甲硅烷氧基膦酸酯的广泛，适用性强，高产率且方便的方法。描述了整洁的条件。为了表明该方法的一般适用性，我们还成功地将该方法用于普通醇和酚的甲硅烷基化。
• Aluminium Triflate [Al(OTf)₃] as a Recyclable Catalyst for the Conversion of α-Hydroxyphosphonates, Alcohols and Phenols to Their Corresponding O-Silylated Products with Hexamethyldisilazane (HMDS)
  作者：Habib Firouzabadi、Nasser Iranpoor、Sara Sobhani、Soheila Ghassamipour

  DOI：10.1055/s-2005-861789

  日期：——

  Al(OTf)3 as a recyclable catalyst conducts the efficient conversion of various types of α-hydroxyphosphonates to their corresponding α-trimethysilyloxyphosphonates with HMDS in the absence of solvent at room temperature. The general applicability of the catalyst under solvent-free conditions is demonstrated by applying it for the successful silylation of alcohols and phenols with HMDS in high yields.

  三氟甲磺酸铝（Al(OTf)3）作为一种可回收催化剂，在室温下无溶剂存在的条件下，能高效地将各种类型的α-羟基膦酸酯转化为相应的α-三甲基硅氧基膦酸酯，使用的是六甲基二硅胺烷（HMDS）。该催化剂在无溶剂条件下的广泛适用性通过其在高产率下成功实现醇和酚与HMDS的硅烷化反应而得到证明。
• Highly Efficient Hydrophosphonylation of Aldehydes and Unactivated Ketones Catalyzed by Methylene-Linked Pyrrolyl Rare Earth Metal Amido Complexes
  作者：Shuangliu Zhou、Zhangshuan Wu、Jiewei Rong、Shaowu Wang、Gaosheng Yang、Xiancui Zhu、Lijun Zhang

  DOI：10.1002/chem.201102207

  日期：2012.2.27

  characterized by 1H NMR spectroscopic analyses. The structures of complexes 2, 3, 4, and 6 were determined by single‐crystal X‐ray analyses. Study of the catalytic activities of the complexes showed that these rare earth metal amido complexes were excellent catalysts for hydrophosphonylations of aldehydes and unactivated ketones. The catalyzed reactions between diethyl phosphite and aldehydes in the presence

  通过甲硅烷基胺消除反应制备了一系列带有亚甲基连接的吡咯基-酰胺基配体的稀土金属酰胺配合物，在无溶剂条件下，液态底物在醛和未活化酮的氢膦酰化反应中显示出很高的催化活性。的治疗[（ME 3 Si）的2 N] 3 LN（μ-Cl）的锂（THF）3与2-（2,6--ME 2 ç 6 ħ 3 NHCH 2）C 4 H ^ 3 NH（1，1个当量）在甲苯，得到相应的式三价稀土金属酰胺（μ-η 5：η 1）：η 1-2-[（2,6-Me 2 C 6 H 3）NCH 2 ]（C 4 H 3 N）LnN（SiMe 3）2 } 2 [Ln = Y（2），Nd（3），Sm（4），Dy（5），Yb（6）]，产量适中。所有化合物均通过光谱法和元素分析充分表征。钇配合物的特征还在于1 H NMR光谱分析。复合物的结构 2，3，4，和6由单晶X射线分析确定。配合物催化活性的研究表明，这些稀土金属酰胺配合物是醛和未活化
• The Synthesis and Herbicidal Evaluation of Fluorine-Containing Phenoxyacetoxyalkylphosphonate Derivatives
  作者：Ting Chen、Ping Shen、Yanjun Li、Hongwu He

  DOI：10.1080/10426500600614253

  日期：2006.9.1

  Compound 5l exhibited notable activity. Results showed that by introducing a fluorine moiety to the parent structure of phenoxyacetoxyalkylphosphonates, a series of new compounds with satisfactory herbicidal activity could be synthesized. A reasonable combination of a fluorine moiety and other substituents on the benzene ring had a great influence on the herbicidal activity.

  为了研究氟部分对苯氧基乙酰氧基烷基膦酸酯的生物活性的影响，合成了一系列含氟苯氧基乙酰氧基烷基膦酸酯并在温室中筛选了除草活性。大多数标题化合物对试验植物，尤其是单子叶植物，显示出比出苗后活性更好的出苗前活性。化合物5l表现出显着的活性。结果表明，通过在苯氧基乙酰氧基烷基膦酸酯的母体结构中引入氟基团，可以合成一系列具有令人满意的除草活性的新化合物。苯环上的氟部分和其他取代基的合理组合对除草活性有很大影响。
• Synthesis and characterization of ytterbium guanidinates stabilized by bridged bis(phenolate) ligand and their application for the hydrophosphonylation reaction of aldehydes
  作者：Tinghua Zeng、Qinqin Qian、Yaorong Wang、Yingming Yao、Qi Shen

  DOI：10.1016/j.jorganchem.2014.12.021

  日期：2015.3

  gave the expected ytterbium guanidinato complexes LYb[R2NC(NR1)2] [R1 = Cy, R2N = N(TMS)2 (1), N(CH2)5 (2); R1 = iPr, R2N = N(TMS)2 (3), NPh2 (4)]. These ytterbium complexes were well characterized by elemental analyses, IR spectroscopy and single-crystal X-ray structure determination. The metal ion is six-coordinated by two oxygen and two nitrogen atoms from the bis(phenolate) ligand, and two nitrogen

  制备了一系列由胺桥联的双酚盐配体稳定的胍基配合物，并探讨了其对醛的羰基化反应的催化性能。复分解胺桥连的双反应（酚盐）镱氯化物LYbCl（THF）[L =我2 NCH 2 CH 2 N CH 2 - （2-OC 6 H ^ 2吨卜2 -3,5-）} 2 ]与相应的胍基锂在THF中的摩尔比为1：1，得到了预期的胍基络合物LYb [R 2 NC（NR 1）2 ] [R 1  = Cy，R 2 N = N（TMS）2（1），N（CH 2）5（2）; R 1  =  i Pr，R 2 N = N（TMS）2（3），NPh 2（4）]。这些element配合物通过元素分析，红外光谱和单晶X射线结构测定得到了很好的表征。金属离子由双（酚盐）配体的两个氧和两个氮原子与一个胍基的两个氮原子六配位。around周围的配位几何可描述为扭曲的八面体。已发现这些these胍基络合物是在温和条件下用于各种醛的氢膦酰化反应的高效催化剂。