(E)-methyl 2-(phthalimidomethyl)but-2-enoate | 351029-39-5

• 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: (E)-methyl 2-(phthalimidomethyl)but-2-enoate
• 英文别名: methyl (E)-2-[(1,3-dioxoisoindol-2-yl)methyl]but-2-enoate
• CAS: 351029-39-5
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: QMKFTUGTSFQSJH-YCRREMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  (E)-methyl 2-(phthalimidomethyl)but-2-enoate 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89%的产率得到methyl 2-(phthalimidomethyl)butanoate
  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
• 作为产物：
  描述：

  1-苯二酰亚氨基-2-丁炔 在 亚磷酸三苯酯 、 四(亚磷酸三苯酯)镍 、 硫酸 作用下， 以 苯 为溶剂， 反应 24.0h， 生成 (E)-methyl 2-(phthalimidomethyl)but-2-enoate
  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

• Enantioselective radical reactions. Evaluation of nitrogen protecting groups in the synthesis of β2-amino acids
  作者：Mukund P. Sibi、Kalyani Patil

  DOI：10.1016/j.tetasy.2006.01.018

  日期：2006.2

  We have investigated the effect of nitrogen protecting groups in radical addition trapping experiments leading to beta(2)-amino acids. Of the three N-protecting groups examined, the phthalimido group was optimal with respect to both yields and enantioselectivity. Additionally, radical additions to more complex acrylates were also investigated, which provided access to functionalized beta(2)-amino acids in modest selectivity. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.