[1-(naphthalen-2-yl)-2,2-dicyanoethyl] phosphonic acid diethyl ester | 1243691-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [1-(naphthalen-2-yl)-2,2-dicyanoethyl] phosphonic acid diethyl ester
• 英文别名: [1-(naphthalen-2-yl)-2,2-dicyanoethyl]phosphonic acid diethyl ester；diethyl 2,2-dicyano-1-(naphthalen-2-yl)ethylphosphonate；2-[[Diethoxy(oxido)phosphaniumyl]-naphthalen-2-ylmethyl]propanedinitrile；2-[[diethoxy(oxido)phosphaniumyl]-naphthalen-2-ylmethyl]propanedinitrile
• CAS: 1243691-62-4
• 化学式: C₁₈H₁₉N₂O₃P
• 分子量: 342.334
• InChiKey: OTZGWMDQVURDDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-naphthylmethylidenemalononitrile 、 亚磷酸三乙酯 在 silica-supported perchloric acid 作用下， 反应 1.0h， 以85%的产率得到[1-(naphthalen-2-yl)-2,2-dicyanoethyl] phosphonic acid diethyl ester
  参考文献：
  名称：

  HClO4-SiO2 as a Novel and Recyclable Catalyst for the Phospha-Michael Addition of Phosphorous Nucleophiles to α,β-Unsaturated Malonates

  摘要：

  描述了一种高效合成β-膦酸丙二酸酯的方法，通过在HClO4-SiO2这一新型且可回收催化剂的存在下，利用磷亲核试剂对α,β-不饱和丙二酸酯进行膦-迈克尔加成反应。

  DOI：

  10.1055/s-0029-1220069

文献信息

• Phospha-Michael addition of phosphorus nucleophiles to α,β-unsaturated malonates using 3-aminopropylated silica gel as an efficient and recyclable catalyst
  作者：Sara Sobhani、Zahra Pakdin Parizi、Soodabeh Rezazadeh

  DOI：10.1016/j.jorganchem.2010.10.015

  日期：2011.2

  gel, which is prepared from commercially available and cheap starting materials, is introduced as an efficient and recyclable catalyst for the phospha-Michael addition of phosphorus nucleophiles to α,β-unsaturated malonates. Short reaction times, mild reaction conditions, ease of recovery and catalyst reusability make this method a new, economic and waste-free chemical process for the synthesis of β-phosphonomalonates

  由市售廉价的起始原料制得的3-氨基丙基化硅胶被引入作为一种有效且可回收的催化剂，用于将磷亲核试剂的磷-迈克尔加成至α，β-不饱和丙二酸酯。反应时间短，反应条件温和，易于回收和催化剂可重复使用，使该方法成为合成β-膦酸二甲酯的经济，无浪费的新化学方法。
• Phosphomolybdic acid: An efficient and reusable catalyst for the synthesis of β-phosphono malonates
  作者：S. Sobhani、S. Rezazadeh

  DOI：10.1007/bf03246216

  日期：2011.3

  Phosphomolybdic acid (H3PMo12O40) is an efficient and reusable catalyst for the synthesis of the phospha-Michael addition of phosphite esters with different types of α,β-unsaturated malonates to produce a variety of β-phosphono malonates.

  磷钼酸（H 3 PMo 12 O 40）是一种有效且可重复使用的催化剂，用于合成具有不同类型的α，β-不饱和丙二酸酯的亚磷酸酯的phospha-Michael加成，以生产各种β-膦酰基丙二酸酯。
• Heterogeneous reusable catalyst, ultrasound energy, and no solvent: a quick and green recipe for one-pot synthesis of β-phosphonomalononitriles at room temperature
  作者：Bashir Ahmad Dar、Nalini Pandey、Snehil Singh、R.K. Bamezai、Meena Sharma、Ram A. Vishwakarma、Baldev Singh

  DOI：10.1016/j.tetlet.2013.11.095

  日期：2014.1

  Clay-supported heteropolyacid catalyst has been prepared and investigated as a novel heterogeneous, reusable and efficient catalyst for the one-pot synthesis of beta-phosphonomalononitriles under ultrasound irradiation at room temperature. Compared with traditional methods, the present method is solvent-free, works under milder and cleaner conditions, furnishes products with higher purity and yields, needs shorter reaction time, easier work-up procedure, and generates less waste. No column purification is required and the products can be purified by simple crystallization. The catalyst can be easily recovered and reused several times without significant loss of its catalytic activity. The catalyst was characterized by scanning electron microscopy, X-ray powder diffraction, and thermal gravimetric, surface area, and elemental analyses. (C) 2013 Elsevier Ltd. All rights reserved.
• Efficient one-pot synthesis of β-phosphono malonates and 2-amino-4H-chromen-4-ylphosphonate derivatives by ethylenediamine diacetate-catalyzed three-component reactions
  作者：Srinivasa Rao Kolla、Yong Rok Lee

  DOI：10.1016/j.tet.2011.10.060

  日期：2012.1

  One-pot three-component reactions of arylaldehyde or salicylaldehyde with malononitrile (or ethyl-cyanoacetate) and triethyl phosphite are carried out in the presence of ethylenediamine diacetate (EDDA) as a catalyst for the synthesis of biologically interesting beta-phosphono malonates and 2-amino-4H-chromen-4-ylphosphonate derivatives. The value of this method lies in its mild reaction catalyst and conditions, good yields, and ease of handling. (C) 2011 Elsevier Ltd. All rights reserved.