(alpha-羟基-4-氯苄基)膦酸二乙酯 | 20641-28-5

• 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-4-氯苄基)膦酸二乙酯
• 英文名称: diethyl (4-chlorophenyl)(hydroxy)methylphosphonate
• 英文别名: diethyl hydroxy(4-chlorophenyl)methylphosphonate；α-hydroxy-4-chloro-benzyl-phosphonic acid diethyl ester；Phosphonic acid, ((4-chlorophenyl)hydroxymethyl)-, diethyl ester；(4-chlorophenyl)-diethoxyphosphorylmethanol
• CAS: 20641-28-5
• 化学式: C₁₁H₁₆ClO₄P
• 分子量: 278.672
• InChiKey: RIQJHXWKWXDLFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  (alpha-羟基-4-氯苄基)膦酸二乙酯 在 potassium permanganate 作用下， 以 苯 为溶剂， 反应 7.0h， 以95%的产率得到(4-chloro-benzoyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  通过在无溶剂条件下用中性氧化铝负载的高锰酸钾（NASPP）和高锰酸钾在无水苯中氧化α-羟基膦酸酯来制备α-酮膦酸酯

  摘要：

  在无溶剂条件下，通过在干苯中的高锰酸钾或中性氧化铝负载的高锰酸钾（NASPP），可以将各种类型的α-羟基膦酸酯高产率地转化为α-酮膦酸酯。

  DOI：

  10.1016/s0040-4039(01)02146-3
• 作为产物：
  描述：

  diethyl α-trimethylsilyloxy-4-chlorobenzylphosphonate 在 氨基磺酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到(alpha-羟基-4-氯苄基)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

• Iron-Doped Single-Walled Carbon Nanotubes as New Heterogeneous and Highly Efficient Catalyst for Acylation of Alcohols, Phenols, Carboxylic Acids and Amines under Solvent-Free Conditions
  作者：Hashem Sharghi、Mahboubeh Jokar、Mohammad Mahdi Doroodmand

  DOI：10.1002/adsc.201000365

  日期：2011.2.11

  single-walled carbon nanotubes (Fe/SWCNTs) represent an efficient and new heterogeneous reusable catalyst for the acylation of a variety of alcohols, phenols, carboxylic acids and amines with acid chlorides or acid anhydrides under solvent-free conditions. The reactions of various primary, secondary, tertiary, and benzylic alcohols, diols, phenols, as well as aromatic and aliphatic amines give acylated

  掺杂铁的单壁碳纳米管（Fe / SWCNT）代表了一种高效且新型的多相可重复使用的催化剂，用于在无溶剂条件下将各种醇，酚，羧酸和胺与酰氯或酸酐酰化。各种伯，仲，叔和苯甲醇，二醇，苯酚以及芳族和脂族胺的反应均以极好的收率得到了酰化的加合物。
• 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。
• Iron(III) trifluoroacetate [Fe(F3CCO2)3] as an easily available, non-hygroscopic, non-corrosive, highly stable and a reusable Lewis Acid catalyst: Efficient O-silylation of α-hydroxyphosphonates, alcohols and phenols by hexamethyldisilazane (HMDS) under solvent-free conditions
  作者：Habib Firouzabadi、Nasser Iranpoor、Abbas Ali Jafari、Mohammad Reza Jafari

  DOI：10.1016/j.jorganchem.2008.05.018

  日期：2008.8

  O-Silylation of hydroxyl groups of α-hydroxyphosphonates, primary, secondary tertiary-alcohols and phenols with HMDS was achieved in high to excellent yields using iron(III) trifluoroacetate [Fe(F3CCO2)3] as an easily available and a cost effective, non-hygroscopic, non-corrosive, highly stable and an efficient catalyst under solvent-free conditions. As a typical reaction, we have scaled up silylation of diphenyl

  ø α-hydroxyphosphonates，伯，仲叔醇和酚与HMDS的羟基-Silylation在实现高使用铁（III）三氟乙酸盐的[Fe（F优异的产率3 CCO 2）3 ]作为容易获得和在无溶剂条件下具有成本效益，不吸湿，不腐蚀，高度稳定和高效的催化剂。作为典型的反应，我们已将二苯甲醇的甲硅烷基化规模扩大到20 mmol的底物，以证明该催化剂对于规模化生产非常有效。通过简单的过滤就可以容易地分离出催化剂，并且可以循环使用该催化剂进行二苯甲硅烷基化反应，而不会失去其催化活性。
• Preparation and characterization of multi-walled carbon nanotubes (MWCNTs), functionalized with phosphonic acid (MWCNTs–C–PO3H2) and its application as a novel, efficient, heterogeneous, highly selective and reusable catalyst for acetylation of alcohols, phenols, aromatic amines, and thiols
  作者：Farzaneh Dehghani、Ali Reza Sardarian、Mohammad Mehdi Doroodmand

  DOI：10.1007/s13738-013-0339-9

  日期：2014.6

  behavior of the MWCNTs–C–PO3H2 catalyst was evaluated using the TG instrumentation system at 25 °C. The catalyst was applied successfully for highly efficient and selective acetylation of alcohols, phenols, thiols and aromatic amines with acetic anhydride at room temperature under solvent-free conditions. The reusability of the catalyst was checked and the recovered catalyst was reused for five runs without

  合成了一种新型，高效，异质且可重复使用的多壁碳纳米管（MWCNT），该碳纳米管已被膦酸官能化（MWCNTs–C–PO 3 H 2）。合成的CNT使用一些电子显微镜技术（例如扫描电子显微镜（SEM），原子力显微镜（AFM），能量色散X射线光谱仪（EDAX））以及一些热学和光谱学方法（例如热重分析（TG））进行了表征。MWCNTs–C–PO 3 H 2的氮吸附行为使用TG仪器系统在25°C下评估催化剂。该催化剂已成功地用于室温下无溶剂条件下用乙酸酐对醇，酚，硫醇和芳族胺进行高效和选择性乙酰化。检查催化剂的可重复使用性，并将回收的催化剂重复使用五次，而活性没有明显损失。