diethyl α-trimethylsilyloxy-4-methoxybenzylphosphonate | 17911-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl α-trimethylsilyloxy-4-methoxybenzylphosphonate
• 英文别名: [Diethoxyphosphoryl-(4-methoxyphenyl)methoxy]-trimethylsilane
• CAS: 17911-20-5
• 化学式: C₁₅H₂₇O₅PSi
• 分子量: 346.436
• InChiKey: KTWANPBVNRCYKW-UHFFFAOYSA-N

物化性质

• 沸点：
  144-145 °C(Press: 0.6 Torr)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl α-trimethylsilyloxy-4-methoxybenzylphosphonate 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 以 四氯化碳 为溶剂， 反应 1.5h， 以85%的产率得到diethyl (4-methoxybenzoyl)phosphonate
  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
• 作为产物：
  描述：

  diethyl (hydroxy(4-methoxyphenyl)methyl)phosphonate 、 六甲基二硅氮烷 在 aluminium(III) triflate 作用下， 以92%的产率得到diethyl α-trimethylsilyloxy-4-methoxybenzylphosphonate
  参考文献：
  名称：

  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)

  摘要：

  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。

  DOI：

  10.1055/s-2005-861789

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 chemo- and regioselective silylation of –OH groups and cyanosilylation of aldehydes promoted by TiCl2(OTf)–SiO2 as a new recyclable catalyst
  作者：Habib Firouzabadi、Nasser Iranpoor、Soghra Farahi

  DOI：10.1016/j.jorganchem.2009.08.009

  日期：2009.11

  TiCl2(OTf)-SiO2 as an easy handling recyclable catalyst was applied for trimethylsilylation of diethyl alpha-hydroxyphosphonates, alcohols and phenols with high selectivity using HMDS as a silylating agent. Cyanotrimethylsilyl ethers were also obtained in excellent yields from treatment of aldehydes with TMSCN in the presence of this catalyst. (C) 2009 Elsevier B.V. All rights reserved.
• A high yielding preparation of α-trimethylsilyloxyphosphonates by silylation of α-hydroxyphosphonates with HMDS catalyzed by iodine
  作者：Habib Firouzabadi、Nasser Iranpoor、Sara Sobhani

  DOI：10.1016/s0040-4039(02)00631-7

  日期：2002.5

  A general, versatile, high yielding and convenient procedure for the immediate conversion of various alpha-hydroxyphosphonates to alpha-trimethylsilyloxyphosphonates under neutral conditions using HMDS in the presence of a catalytic amount of iodine is described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Copper triflate [Cu(OTf)2] is an efficient and mild catalyst for the silylation of α-hydroxyphosphonates to α-trimethylsilyloxyphosphonates with HMDS at room temperature
  作者：Habib Firouzabadi、Nasser Iranpoor、Sara Sobhani、Soheila Ghassamipour、Zohreh Amoozgar

  DOI：10.1016/s0040-4039(02)02780-6

  日期：2003.1

  A broad, adaptable, high yielding and convenient procedure for the fast conversion of various alpha-hydroxyphosphonates to alpha-trimethylsilyloxyphosphonates under mild conditions with HMDS in the presence of a catalytic amount of copper triflate is described. This procedure has also been applied successfully for the silylation of alcohols and phenols. (C) 2003 Elsevier Science Ltd. All rights reserved.