[1-(4-chlorophenyl)-2-cyano-2-ethylcarboxylic acid ethyl ester]phosphonic acid diethyl ester | 22730-59-2

• 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: [1-(4-chlorophenyl)-2-cyano-2-ethylcarboxylic acid ethyl ester]phosphonic acid diethyl ester
• 英文别名: [1-(4-chlorophenyl)-2-cyano-2-(ethoxycarbonyl)ethyl]phosphonic acid diethyl ester；ethyl 3-(4-chlorophenyl)-2-cyano-3-(diethoxyphosphoryl)propanoate；Ethyl 3-(4-chlorophenyl)-2-cyano-3-diethoxyphosphorylpropanoate
• CAS: 22730-59-2
• 化学式: C₁₆H₂₁ClNO₅P
• 分子量: 373.773
• InChiKey: ANZCNEMAIXPFDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(4-氯苯基)-2-氰基丙烯酸乙酯 、 亚磷酸二乙酯 在 nanoflake zinc oxide 作用下， 反应 7.5h， 以98%的产率得到[1-(4-chlorophenyl)-2-cyano-2-ethylcarboxylic acid ethyl ester]phosphonic acid diethyl ester
  参考文献：
  名称：

  Nanosized zinc oxide as a catalyst for the rapid and green synthesis of β-phosphono malonates

  摘要：

  The design and development of a nano heterogeneous catalyst for the direct addition of P(O)-H bonds across various alkylidenes under solvent-free conditions is described. This is a mild, rapid, and efficient protocol to generate P-C bonds. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.03.095

文献信息

• A quaternary ammonium salt [H-dabco][AcO]: as a recyclable and highly efficient catalyst for the one-pot synthesis of β-phosphonomalonates
  作者：Ya-Qin Yu、Da-Zhen Xu

  DOI：10.1039/c5ra02743h

  日期：——

  A simple, green and highly efficient approach for the one-pot three-component synthesis of β-phosphonomalonates has been developed. In the presence of the quaternary ammonium salt catalysts, the β-phosphonomalonates were obtained in excellent yields within short times via tandem Knoevenagel–phospha-Michael reaction. The reaction of aldehydes/ketones, active methylene compounds, and diethyl phosphite

  已经开发出一种简单，绿色且高效的方法，用于一锅三组分合成β-膦酰基丙二酸酯。在季铵盐催化剂的存在下，通过Knoevenagel-phospha-Michael反应串联，可在短时间内以优异的产率获得β-膦酰基丙二酸酯。醛/酮，活性亚甲基化合物和亚磷酸二乙酯的反应在室温，无溶剂条件下进行。不需要柱纯化，并且可以通过简单的结晶纯化产物。催化剂可以容易地回收并重复使用几次，而不会显着降低活性。
• 5-Hydroxypentylammonium acetate as a reusable ionic liquid catalyzes tandem Knoevenagel-phospha-Michael reaction of aldehydes, malononitrile and phosphites
  作者：S. Sobhani、M. Honarmand

  DOI：10.1007/s13738-012-0088-1

  日期：2012.10

  5-Hydroxypentylammonium acetate as a task-specific ionic liquid promotes efficient tandem Knoevenagel-phospha-Michael reaction of phosphite esters with aryl/heteroaryl/alkyl/salicylaldehydes and malonitrile/ethyl cyanoacetate at room temperature in short reaction times. This simple procedure allows a series of β-phosphonomalonates and 4-substituted 2-amino-4H-chromenes with phosphonic acid dialkyl esters to be synthesized in good to high yields in the presence of an ionic liquid for the first time.

  5-羟基戊基铵乙酸盐作为一种特定任务的离子液体，促进了在室温下快速反应的磷酸酯与芳基/杂芳基/烷基/水杨醛和丙二腈/乙基氰乙酸酯的高效串联Knoevenagel-磷法-迈克尔反应。这一简单的方法首次在离子液体存在下合成了一系列β-磷酸马隆酸酯和4-取代的2-氨基-4H-色烯，产率良好至高。
• Lanthanum(<scp>iii</scp>) triflate supported on nanomagnetic γ-Fe₂O₃: a new magnetically recyclable heterogeneous Lewis acid for the one-pot synthesis of β-phosphonomalonates
  作者：Sara Sobhani、Zahra Pakdin-Parizi

  DOI：10.1039/c4ra00543k

  日期：——

  A new magnetically recyclable heterogeneous Lewis acid was synthesized and used for the one-pot synthesis of β-phosphonomalonates.

  一种新的可磁性回收的非均相路易斯酸被合成，并用于β-磷酸马隆酸酯的一锅合成。
• Nano n-propylsulfonated γ-Fe2O3 as magnetically recyclable heterogeneous catalyst for the efficient synthesis of β-phosphonomalonates
  作者：Sara Sobhani、Zahra Pakdin Parizi、Nasrin Razavi

  DOI：10.1016/j.apcata.2011.09.039

  日期：2011.12

  nanomagnetic iron oxide was synthesized directly through ring opening reaction of 1,3-propanesultone with nano magnetic γ-Fe2O3 and used as magnetically recyclable heterogeneous catalyst for the efficient one-pot synthesis of β-phosphonomalonates. The catalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused at least five times without significant degradation

  纳米Ñ -propylsulfonated了γ-Fe 2 ö 3作为新的磺化的纳米磁性氧化铁纳米磁性直接合成通过1,3-丙磺酸内酯的开环反应了γ-Fe 2 ö 3和用作磁可回收的非均相催化剂为高效一个锅合成β-膦酰基膦酸酯。通过使用外部磁体的磁倾析，容易地从反应混合物中分离出催化剂，并重复使用至少五次而活性没有明显降低。
• An eco-friendly procedure for one-pot synthesis of β-phosphonomalonates: micellar solution of sodium stearate catalyzes tandem Knoevenagel–phospha-Michael reaction of aldehydes, malonitrile, and phosphites in aqueous media
  作者：Sara Sobhani、Zahra Pakdin Parizi

  DOI：10.1016/j.tet.2011.03.014

  日期：2011.5

  A new, one-pot convenient method for the synthesis of a variety of β-phosphonomalonates by a tandem Knoevenagel–phospha-Michael reaction of phosphite esters with aryl/heteroaryl/alkyl aldehydes and malonitrile in an aqueous micellar solution of sodium stearate is described. This method offers several advantages, such as using a cheap and environmentally benign reaction media, low loadings of sodium

  描述了一种在硬脂酸钠胶束水溶液中通过亚磷酸酯与芳基/杂芳基/烷基醛和丙二酸的串联Knoevenagel-phospha-Michael反应来合成各种β-膦酰基丙酸酯的简便方法。该方法具有许多优点，例如使用便宜且对环境无害的反应介质，低负荷的硬脂酸钠作为催化剂，并提供了良好的收率。