3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid ethyl ester

• 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: 3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid ethyl ester
• 英文别名: ethyl 3-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate；ethyl 3-(1,3-dioxoisoindol-2-yl)-3-phenylpropanoate
• 化学式: C₁₉H₁₇NO₄
• 分子量: 323.348
• InChiKey: SSHVQKAAMPPROG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (Z)-ethyl 3-phthalimido-3-phenylpropenoate 在 {bis[(Sb)-4-(N-tolylamino)dinaphtho[2,1-d:1',2'-f]-[1,3,2]dioxaphosphepine]}(η-cycloocta-1,5-diene)rhodium(I) tetrafluoroborate 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 40.0 ℃ 、3.55 MPa 条件下， 反应 5.0h， 生成 3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-phenylpropionic acid ethyl ester
  参考文献：
  名称：

  The use of new chiral phosphite and amidophosphite ligands in the Rh-catalyzed hydrogenation of dehydro-β-amino acid derivatives

  摘要：

  合成了新型手性膦酯类配体。这些配体在不对称的铑催化氢化N-乙酰脱氢β-氨基酸酯的实验中表现出了高的对映体选择性（最高可达75% ee）。发现邻苯二甲酰亚胺对二取代炔烃的亲核加成反应，为获得N-邻苯二甲酰脱氢β-氨基酸酯提供了途径。与常见有机溶剂相比，在氟化醇中对N-乙酰和N-邻苯二甲酰脱氢β-氨基酸衍生物的氢化反应中观察到了更高的转化率和对映体选择性。

  DOI：

  10.1007/s11172-011-0315-4

文献信息

• A Convenient Synthesis and the Asymmetric Hydrogenation of <i>N</i>-Phthaloyl Dehydroamino Acid Esters
  作者：Jian Chen、Qiang Liu、Weicheng Zhang、Stephen Spinella、Aiwen Lei、Xumu Zhang

  DOI：10.1021/ol800996j

  日期：2008.7.17

  A convenient synthetic method was reported for the preparation of N-phthaloyl dehydroamino acid esters from easily accessible vinyl bromides (or vinyl tosylate) and potassium phthalimide. Rh-catalyzed asymmetric hydrogenation of these substrates with TangPhos gave the products with good to excellent enantioselectivities (up to 99% ee).

  据报道，一种方便的合成方法是从容易获得的乙烯基溴化物（或甲苯磺酸乙烯基酯）和邻苯二甲酰亚胺钾盐制备N-邻苯二甲酰基脱氢氨基酸酯。用TangPhos对这些底物进行Rh催化的不对称氢化，使产物具有良好的至优异的对映选择性（高达99％ee）。
• Synthesis and characterization of a magnetically separable novel FeO@L-DOPA@Cu nanocatalyst (L-DOPA = L-3,4-dihydroxyphenyylalanine): Asymmetric aza-Michael addition reaction
  作者：Arnab Datta、Jaydeep Adhikary、Sourav Chatterjee、Debasish Ghosh、Saikat Khamarui、Tanmay Chattopadhyay

  DOI：10.1016/j.ica.2016.02.019

  日期：2016.4

  The synthesis and characterization of new copper(II)-L-3,4-dihydroxyphenyylalanine based magnetically separable nanocatalyst, namely Fe3O4@L-DOPA@Cu-II (L-DOPA = L-3,4-dihydroxyphenyylalanine), are described. The catalyst has been characterized by physicochemical studies. We have studied the application of this new catalyst for asymmetric aza-Michael addition reaction. This catalyst could simply be separated and recovered from the reaction mixture with the assistance of an external magnet and reused several times. (C) 2016 Elsevier B.V. All rights reserved.
• The use of new chiral phosphite and amidophosphite ligands in the Rh-catalyzed hydrogenation of dehydro-β-amino acid derivatives
  作者：S. E. Lyubimov、E. A. Rastorguev、P. V. Petrovskii、V. A. Davankov

  DOI：10.1007/s11172-011-0315-4

  日期：2011.10

  New chiral phosphite-type ligands were synthesized. The tests of these ligands in the asymmetric Rh-catalyzed hydrogenation of N-acetyl derivatives of dehydro-β-amino acid esters showed their high enantioselectivity (up to 75% ee). The reaction of nucleophilic addition of phthalimide to disubstituted alkynes offering access to esters of N-phthaloyldehydro-β-amino acids was discovered. Higher conversion and enantioselectivity in the hydrogenation of N-acetyl and N-phtaloyl derivatives of dehydro-β-amino acids were observed in fluorinated alcohols as compared to common organic solvents.

  合成了新型手性膦酯类配体。这些配体在不对称的铑催化氢化N-乙酰脱氢β-氨基酸酯的实验中表现出了高的对映体选择性（最高可达75% ee）。发现邻苯二甲酰亚胺对二取代炔烃的亲核加成反应，为获得N-邻苯二甲酰脱氢β-氨基酸酯提供了途径。与常见有机溶剂相比，在氟化醇中对N-乙酰和N-邻苯二甲酰脱氢β-氨基酸衍生物的氢化反应中观察到了更高的转化率和对映体选择性。