diethyl α-hydroxy(2-naphthylmethyl)-phosphonate | 1090-99-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl α-hydroxy(2-naphthylmethyl)-phosphonate
• 英文别名: diethyl [hydroxy(naphthalen-2-yl)methyl]phosphonate；diethyl hydroxy(naphthalen-2-yl)methylphosphonate；diethyl α-hydroxy-2-naphthylphosphonate；diethoxyphosphoryl(naphthalen-2-yl)methanol
• CAS: 1090-99-9；1012787-52-8；1042417-52-6
• 化学式: C₁₅H₁₉O₄P
• 分子量: 294.287
• InChiKey: NHUKCEPJWOWGLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl α-hydroxy(2-naphthylmethyl)-phosphonate 在 zinc dichromate(VI) 作用下， 以91%的产率得到diethyl P-(naphthalen-2-ylcarbonyl)phosphonate
  参考文献：
  名称：

  通过在无溶剂条件下用重铬酸锌三水合物（ZnCr 2 O 7 ·3H 2 O）氧化α-羟基膦酸酯来高产率地制备α-酮膦酸酯

  摘要：

  通过三水合重铬酸锌在无溶剂条件下以高收率和高产率将各种类型的α-羟基膦酸酯转化为α-酮膦酸酯。

  DOI：

  10.1016/s0040-4039(01)00712-2
• 作为产物：
  描述：

  二乙基亚磷酸氢酯 、 2-萘甲醛 在 1,3-双(2,6-二异丙基苯基)咪唑-2-烯 作用下， 以 二氯甲烷 为溶剂， 反应 60.0h， 以63%的产率得到diethyl α-hydroxy(2-naphthylmethyl)-phosphonate
  参考文献：
  名称：

  N-Heterocyclic Carbenes Catalyzed Phospho-Aldol Reaction of Aldehydes

  摘要：

  AbstractAn efficient phospho‐aldol reaction of aldehydes catalyzed by N‐heterocyclic carbenes (NHCs) has been developed. With 10 mol% stable NHC 1,3‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene, various aldehydes reacted with dialkylphosphites smoothly to provide α‐hydroxy phosphonates in 59% –99% yield. In this process, NHC was assumed to function as a carbon‐centered br?nsted base.

  DOI：

  10.1002/cjoc.201300615

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。
• Enantioselective Acylphosphonylation—Dual Lewis Acid–Lewis Base Activation of Aldehyde and Acylphosphonate
  作者：Ye-Qian Wen、Robin Hertzberg、Christina Moberg

  DOI：10.1021/jo500895u

  日期：2014.7.3

  obtained by a one-step procedure consisting of reaction of diethyl acetylphosphonate with prochiral aldehydes in the presence of a catalytic system comprising a chiral Lewis acid, an achiral Lewis base, and a Brønstedt base. Best results were obtained using a tridentate Schiff base aluminum(III) Lewis acidic complex, 1H-1,2,3-benzotriazole, and a tertiary amine such as DBU. The target compounds were

  乙酰氧基膦酸酯是通过一步法获得的，该过程由乙酰膦酸二乙酯与前手性醛在包含手性路易斯酸，非手性路易斯碱和布朗斯台德碱的催化体系的存在下反应组成。使用三齿Schiff碱铝（III）Lewis酸性配合物，1 H -1,2,3-苯并三唑和叔胺（例如DBU ）可获得最佳结果。在大多数情况下，以高收率获得目标化合物，但对映体比例适中（最高78:22）。
• Asymmetric hydrophosphonylation of aldehydes catalyzed by bifunctional chiral Al(III) complexes
  作者：Shaohua Gou、Xin Zhou、Jun Wang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1016/j.tet.2008.01.022

  日期：2008.3

  effective enantioselective hydrophosphonylation of aldehydes. A variety of aromatic, heteroaromatic, condensed-ring, α,β-unsaturated, and aliphatic aldehydes were found to be suitable substrates for the reaction, and the desired α-hydroxy phosphonate were obtained in good to excellent yields (up to 99%) with moderate to good enantioselectivities (up to 87% ee) under mild conditions (at 0 °C). A possible

  一种新的手性双官能的Al（Ⅲ）配合物的BINOL衍生物，其中载有叔在BINOL的3,3'-位置-胺，已发展为醛的对映选择性有效hydrophosphonylation。发现各种芳族，杂芳族，稠环，α，β-不饱和和脂族醛是反应的合适底物，并且以良好或优异的收率（高达99％）获得了所需的α-羟基膦酸酯。在温和条件下（0°C）具有中等至良好的对映选择性（高达87％ee）。根据实验结果提出了可能的催化循环。
• MgO-coated-Fe3O4 nanoparticles as a magnetically recoverable and reusable catalyst for the synthesis of 1-hydroxyphosphonates
  作者：Babak Kaboudin、Foad Kazemi、Fereshteh Habibi

  DOI：10.1007/s13738-014-0504-9

  日期：2015.3

  Nanosize magnetic particles coated with magnesium oxide (core/shell nanoparticles) have been prepared and used for the synthesis of 1-hydroxyalkyl phosphonates. Catalytic activity studies show that the magnetic particles coated with magnesium oxide have highly catalytic activity toward the phosphorylation of aldehydes for the synthesis of 1-hydroxyalkyl phosphonates under solvent-free conditions. Reusability of the prepared magnetic nanoparticles was successfully examined five times with a very slight loss of catalytic activity.

  制备了涂覆有氧化镁的纳米磁性颗粒（核/壳纳米粒子），并用于合成1-羟基烷基磷酸酯。催化活性研究表明，涂覆有氧化镁的磁性颗粒在无溶剂条件下对醛类的磷酸化反应显示出很高的催化活性，用于合成1-羟基烷基磷酸酯。所制备的磁性纳米颗粒经过五次成功的重复使用，催化活性仅有非常轻微的损失。