(1,1-dicyanopentan-2-yl)phosphonic acid diethyl ester | 1243691-66-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (1,1-dicyanopentan-2-yl)phosphonic acid diethyl ester
• 英文别名: [1,1-dicyanopentan-2-yl]phosphonic acid diethyl ester；1,1-dicyanopentan-2-yl phosphonic acid diethyl ester；Diethyl 1,1-dicyanopentan-2-ylphosphonate；2-(1-diethoxyphosphorylbutyl)propanedinitrile
• CAS: 1243691-66-8
• 化学式: C₁₁H₁₉N₂O₃P
• 分子量: 258.257
• InChiKey: QPBZPPLQIXDLNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  butylidene-propanedinitrile 、 亚磷酸三乙酯 在 silica-supported perchloric acid 作用下， 反应 0.25h， 以80%的产率得到(1,1-dicyanopentan-2-yl)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

• 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。
• 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。
• Piperidine and Piperazine Immobilized on Iron Oxide Nanoparticles as Magnetically Recyclable Heterogeneous Catalysts for One-Pot Synthesis of β-Phosphonomalonates
  作者：Sara Sobhani、Maryam Sadat Ghasemzadeh、Moones Honarmand

  DOI：10.1007/s10562-014-1297-2

  日期：2014.9

  of chloro-functionalized γ-Fe2O3@SiO2 with piperidine and piperazine, respectively. The resulting bases were employed as magnetically recyclable heterogeneous catalysts for the efficient one-pot three-component synthesis of β-phosphonomalonates. The catalysts were easily separated from the reaction mixture by using a magnet and recycled for five times without significant loss of the catalytic activity

  通过氯官能化的γ-Fe2O3@SiO2分别与哌啶和哌嗪反应，合成了固定在二氧化硅包覆的γ- 磁性纳米颗粒上的哌啶和哌嗪作为新型载体。所得碱用作可磁性回收的多相催化剂，用于高效一锅三组分合成β-膦酰基丙二酸酯。使用磁铁可以很容易地将催化剂从反应混合物中分离出来，并循环使用 5 次，催化活性没有显着损失。
• Pyridine-grafted graphene oxide: a reusable acid–base bifunctional catalyst for the one-pot synthesis of β-phosphonomalonates via a cascade Knoevenagel–phospha Michael addition reaction in water
  作者：Sara Sobhani、Farzaneh Zarifi

  DOI：10.1039/c5ra13083b

  日期：——

  different methods such as FT-IR, XRD, TGA, TEM, SEM, EDS, UV-Vis and elemental analysis and employed as a reusable acid–base bifunctional catalyst for the one-pot synthesis of β-phosphonomalonates via a cascade Knoevenagel–phospha Michael addition reaction of aldehydes, malononitrile and dialkyl phosphites in water.

  通过将吡啶后接枝到GO上，合成了一种新的酸碱双功能催化剂。这种新催化剂的特征在于采用多种方法进行表征，例如FT-IR，XRD，TGA，TEM，SEM，EDS，UV-Vis和元素分析，并用作可重复使用的酸碱双功能催化剂，用于一锅法合成β-膦酰基丙二酸酯通过在水中的醛，丙二腈和亚磷酸二烷基酯级联的Knoevenagel-phospha Michael加成反应。
• 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。