methyl 2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanoate | 879027-00-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanoate
• 英文别名: methyl 2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(4-methoxyphenyl)propanoate；methyl 2-(1,3-dioxoisoindol-2-yl)-3-(4-methoxyphenyl)propanoate
• CAS: 879027-00-6
• 化学式: C₁₉H₁₇NO₅
• 分子量: 339.348
• InChiKey: KLZSLLPDSLRSDJ-UHFFFAOYSA-N

物化性质

• 沸点：
  502.6±45.0 °C(Predicted)
• 密度：
  1.308±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 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：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanoate 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 四氯化碳 、 水 、 丙酮 为溶剂， 生成 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester
  参考文献：
  名称：

  Substituent effects in the stereoconvergent synthesis of β-hydroxyphenylalanine derivatives

  摘要：

  The degree of stereoconvergence in the synthesis of beta-hydroxyarylalanine derivatives from the corresponding beta-bromoarylalanine derivatives is governed by the electronic nature of the aryl substituents, and controlled by facially selective stabilisation of the benzylic cation through the neighbouring ester moiety. introduction of electron donating aryl substituents results in a decrease in selectivity, whereas electron withdrawing substituents induce an increase in selectivity for the threo-beta-hydroxyarylalanine diastereomer. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01314-2
• 作为产物：
  描述：

  methyl 2-bromo-3-(4-methoxyphenyl)propanoate 、 potassium phtalimide 在 N,N-二甲基甲酰胺 作用下， 生成 methyl 2-(1,3-dioxoisoindolin-2-yl)-3-(4-methoxyphenyl)propanoate
  参考文献：
  名称：

  Maimind et al., Zhurnal Obshchei Khimii, 1956, vol. 26, p. 2313,2315; engl. Ausg. S. 2587, 2589

  摘要：

  DOI：

文献信息

• Anchimeric Assistance in Hydrogen-Atom Transfer to Bromine
  作者：Anna K. Croft、Christopher J. Easton

  DOI：10.1071/ch04058

  日期：——

  N-bromosuccinimide exhibit anchimeric assistance by neighbouring ester and amido groups. Rate enhancement occurs through electron donation to the electropositive carbon centre that develops in the transition state of the hydrogen-atom transfer to bromine. The extent of the effect depends on the electron demand at the benzylic position and the electron-donating ability of the neighbouring group.

  一系列苯丙氨酸衍生物和苯甲酸苯甲酸苯酯和 N-苯烷基酰胺与 N-溴代琥珀酰亚胺的自由基苄基溴化表现出相邻酯和酰胺基团的非嵌合辅助。速率提高是通过向正电碳中心提供电子而发生的，该碳中心在氢原子转移到溴的过渡态中发展。影响的程度取决于苄基位置的电子需求和相邻基团的给电子能力。
• Dual Ligand-Enabled Nondirected C−H Olefination of Arenes
  作者：Hao Chen、Philipp Wedi、Tim Meyer、Ghazal Tavakoli、Manuel van Gemmeren

  DOI：10.1002/anie.201712235

  日期：2018.2.23

  The application of the Pd‐catalyzed oxidative C−H olefination of arenes, also known as the Fujiwara–Moritani reaction, has traditionally been limited by the requirement for directing groups on the substrate or the need to use the arene in large excess, typically as a (co)solvent. Herein the development of a catalytic system is described that, through the combined action of two complementary ligands

  传统上，Pd催化芳烃的氧化CH H烯化反应（也称为Fujiwara-Moritani反应）的应用受到在基团上引导基团的要求或大量使用芳烃的需求的限制，通常是（共）溶剂。本文描述了一种催化系统的开发，该催化系统通过两个互补配体的共同作用，使得首次将无直接基团的芳烃用作限制试剂成为可能。反应在空间控制和电子控制的结合下进行，并且能够将这种强大的反应应用于有价值的芳烃，而这些芳烃不能过量利用。
• Ligand-Promoted Non-Directed C−H Cyanation of Arenes
  作者：Luo-Yan Liu、Kap-Sun Yeung、Jin-Quan Yu

  DOI：10.1002/chem.201805772

  日期：2019.2.11

  article reports the first example of a 2-pyridone accelerated non-directed C-H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment (kH /kD =4.40) indicates that the C-H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable

  本文报道了使用芳烃作为限制剂的2-吡啶酮加速非定向CH氰化的第一个实例。该协议与广泛的芳烃兼容，包括先进的中间体，药物分子和天然产物。动力学同位素实验（kH / kD = 4.40）表明，CH键的裂解是限速步骤。而且，该反应易于扩展，进一步显示了该方法的合成效用。
• Maimind et al., Zhurnal Obshchei Khimii, 1956, vol. 26, p. 2313,2315; engl. Ausg. S. 2587, 2589
  作者：Maimind et al.

  DOI：——

  日期：——
• Substituent effects in the stereoconvergent synthesis of β-hydroxyphenylalanine derivatives
  作者：Craig A. Hutton

  DOI：10.1016/s0040-4039(97)01314-2

  日期：1997.8

  The degree of stereoconvergence in the synthesis of beta-hydroxyarylalanine derivatives from the corresponding beta-bromoarylalanine derivatives is governed by the electronic nature of the aryl substituents, and controlled by facially selective stabilisation of the benzylic cation through the neighbouring ester moiety. introduction of electron donating aryl substituents results in a decrease in selectivity, whereas electron withdrawing substituents induce an increase in selectivity for the threo-beta-hydroxyarylalanine diastereomer. (C) 1997 Elsevier Science Ltd.