diethyl 3-phthalimido-2-oxopropylphosphonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: diethyl 3-phthalimido-2-oxopropylphosphonate
• 英文别名: 2-(3-Diethoxyphosphoryl-2-oxopropyl)isoindole-1,3-dione
• 化学式: C₁₅H₁₈NO₆P
• 分子量: 339.285
• InChiKey: WDVWBYYVQSUGNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 3-phthalimido-2-oxopropylphosphonate 在 KF-alumina (50percent w/w) 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以93%的产率得到2,3-Dihydro-5H-pyrrolo<1,2-a>isoindole-2,5-dione
  参考文献：
  名称：

  Efficient Horner–Wadsworth–Emmons intramolecular cyclisation of a N-substituted phthalimide promoted by KF-Alumina: a general tool for the synthesis of functionalised isoindolinones

  摘要：

  An intramolecular Horner-Wadsworth-Emmons reaction promoted by KF-Alumina involving a N-substituted phthalimide, cleanly and efficiently furnishes an interesting alpha,beta-unsaturated tricyclic enone which may undergo selective alkylations at the alpha'-position. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.04.029
• 作为产物：
  描述：

  邻苯二甲酰甘氨酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 magnesium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 diethyl 3-phthalimido-2-oxopropylphosphonate
  参考文献：
  名称：

  单齿亚磷酰胺 的Rh（i）配合物催化α-或β-酰氧基α，β-不饱和膦酸酯的不对称氢化† ‡

  摘要：

  已经公开了带有伯胺部分（DpenPhos）的单齿亚磷酰胺的Rh（I）配合物对于多种α-或β-酰氧基α，β-不饱和膦酸酯的不对称氢化非常有效，从而提供了相应的生物学作用。重要的具有出色对映选择性（90-> 99％ee）的手性α-或β-羟基膦酸衍生物。

  DOI：

  10.1039/c1ob06835k

文献信息

• 3-Imidoallenylphosphonates: <i>In Situ</i> Formation and β-Alkoxylation
  作者：Jan K. E. T. Berton、Thomas S. A. Heugebaert、Wouter Debrouwer、Christian V. Stevens

  DOI：10.1021/acs.orglett.5b03314

  日期：2016.1.15

  ates, allenes bearing both an electron-withdrawing and -donating group, were isolated for the first time. An alkoxy substituent was introduced into these unprecedented intermediates in a one-pot approach, yielding β-functionalized aminophosphonates in excellent yields and short reaction times. The mechanistic insights gained are important additions to the domain of allene chemistry. Addition of biologically

  首次分离了同时带有吸电子和供电子基团的烯丙基3-亚氨基烯基膦酸酯。通过一锅法将烷氧基取代基引入这些前所未有的中间体中，从而以优异的产率和较短的反应时间生成β-官能化的氨基膦酸酯。所获得的机械学见解是对丙二烯化学领域的重要补充。加入重要的生物分子，包括甘油单酸酯，氨基酸和核苷，证明了所开发方法的普遍适用性。
• Acylation of Diethyl Phosphonoacetic Acid Via the MgCl₂/Et₃N System: A Practical Synthesis of β-Keto Phosphonates
  作者：Bernard Corbel、Isabelle L'hostis-Kervella、Jean-Pierre Haelters

  DOI：10.1080/00397910008087362

  日期：2000.2

  A one pot simple procedure for the synthesis of beta-keto phosphonates has been developed using the MgCl2/Et3N base system to generate the magnesium enolate of diethyl phosphonoacetic acid. This intermediate reacts with acid chlorides or imidazolides to give, after workup, the title compounds in good yields.
• On A Safe and Practical Method for The Preparation of β-Keto Phosphonates¹
  作者：Bernard Corbel、Isabelle L'Hostis-Kervella、Jean-Pierre Haelters

  DOI：10.1080/00397919608004568

  日期：1996.7

  Acylations of the magnesium enolate derivatives of trimethyl and triethylphosphonoacetates, using a magnesium chloride-triethylamine system, lead to 2-acylphosphonoacetates which are decarbalkoxylated to give beta-keto phosphonates.
• Asymmetric hydrogenation of α- or β-acyloxy α,β-unsaturated phosphonates catalyzed by a Rh(i) complex of monodentate phosphoramidite
  作者：Jinzhu Zhang、Kaiwu Dong、Zheng Wang、Kuiling Ding

  DOI：10.1039/c1ob06835k

  日期：——

  The Rh(I) complex of a monodentate phosphoramidite bearing a primary amine moiety (DpenPhos) has been disclosed to be highly efficient for the asymmetric hydrogenation of a variety of α- or β-acyloxy α,β-unsaturated phosphonates, providing the corresponding biologically important chiral α- or β-hydroxy phosphonic acid derivatives with excellent enantioselectivities (90–>99% ee).

  已经公开了带有伯胺部分（DpenPhos）的单齿亚磷酰胺的Rh（I）配合物对于多种α-或β-酰氧基α，β-不饱和膦酸酯的不对称氢化非常有效，从而提供了相应的生物学作用。重要的具有出色对映选择性（90-> 99％ee）的手性α-或β-羟基膦酸衍生物。
• Efficient Horner–Wadsworth–Emmons intramolecular cyclisation of a N-substituted phthalimide promoted by KF-Alumina: a general tool for the synthesis of functionalised isoindolinones
  作者：Vittorio Pace、Fernando Martínez、Clara I. Nova、María Fernández、José Vicente Sinisterra、Andrés R. Alcántara

  DOI：10.1016/j.tetlet.2009.04.029

  日期：2009.6

  An intramolecular Horner-Wadsworth-Emmons reaction promoted by KF-Alumina involving a N-substituted phthalimide, cleanly and efficiently furnishes an interesting alpha,beta-unsaturated tricyclic enone which may undergo selective alkylations at the alpha'-position. (C) 2009 Elsevier Ltd. All rights reserved.