methyl 2-methyl-3-phthalimidopropanoate | 96296-40-1

• 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: methyl 2-methyl-3-phthalimidopropanoate
• 英文别名: (+/-)-α-Methyl-β-phthalimido-propionsaeure-methylester；2-methyl-3-phthalimido-propionic acid methyl ester；3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-methyl-propionic acid methyl ester；methyl 3-(1,3-dioxoisoindol-2-yl)-2-methylpropanoate
• CAS: 96296-40-1
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: HSTHOYMDWCXISX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  methyl 2-((1,3-dioxoisoindolin-2-yl)methyl)acrylate 在 Lindlar's catalyst 氢气 作用下， 以 乙酸乙酯 为溶剂， 70.0 ℃ 、999.74 kPa 条件下， 反应 16.0h， 以91%的产率得到methyl 2-methyl-3-phthalimidopropanoate
  参考文献：
  名称：

  A new enantioselective synthesis of β-amino acids

  摘要：

  Enantioselective hydrogenation of some alpha,beta -unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the alpha -carbon using Rh-DuPHOS catalysts afforded beta -amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the alpha,beta -unsaturated methyl esters using a Ru-BINAP catalyst gave higher e.e.s of up to 84%. Method development for the determination of the enantiomeric excesses of these derivatives using chiral HPLC is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00097-0

文献信息

• Towards “homeopathic” palladium-catalysed alkoxycarbonylation of aliphatic and aromatic olefins
  作者：Weiheng Huang、Ralf Jackstell、Robert Franke、Matthias Beller

  DOI：10.1039/d3cc02277c

  日期：——

  Palladium-catalysed alkoxycarbonylation of alkenes allows for atom-efficient synthesis of esters from easily available alkenes in an industrially viable manner. One of the major costs associated with this process is the consumption of the catalyst system. Hence, for economic and ecologic reasons it is desirable to minimize the amount of metal and ligands wherever possible. Herein, we report “a homeopathic”

  钯催化的烯烃烷氧基羰基化允许以工业上可行的方式从容易获得的烯烃原子有效地合成酯。与该过程相关的主要成本之一是催化剂系统的消耗。因此，出于经济和生态原因，希望尽可能减少金属和配体的量。在此，我们报告了在相对温和的条件下“顺势疗法”钯催化的烯烃烷氧基羰基化反应。成功的关键是自制配体 LIKATphos 提供良好至优异的酯产品收率，催化剂周转数在 10 6范围内。
• A new enantioselective synthesis of β-amino acids
  作者：Dilek Saylik、Eva M. Campi、Andrew C. Donohue、W.Roy Jackson、Andrea J. Robinson

  DOI：10.1016/s0957-4166(01)00097-0

  日期：2001.3

  Enantioselective hydrogenation of some alpha,beta -unsaturated nitriles and their corresponding methyl esters bearing a phthalimidomethyl substituent at the alpha -carbon using Rh-DuPHOS catalysts afforded beta -amino acid precursors with modest e.e.s of up to 48%. Hydrogenation of the alpha,beta -unsaturated methyl esters using a Ru-BINAP catalyst gave higher e.e.s of up to 84%. Method development for the determination of the enantiomeric excesses of these derivatives using chiral HPLC is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.