(S)-ethyl 3-phenyl-4-phthalimidobutanoate

• 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: (S)-ethyl 3-phenyl-4-phthalimidobutanoate
• 英文别名: ethyl (S)-3-phenyl-4-phthalimidobutanoate；ethyl (3S)-4-(1,3-dioxoisoindol-2-yl)-3-phenylbutanoate
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: BGIVZCAEHKOMAZ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4-溴巴豆酸乙酯 在 [{(R,R)-1,2-bis(tert-butylsulfinyl)benzene}RhCl]2 、 potassium hydroxide 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 (S)-ethyl 3-phenyl-4-phthalimidobutanoate
  参考文献：
  名称：

  Rhodium-catalyzed asymmetric addition of arylboronic acids to γ-phthalimido-substituted-α,β-unsaturated carboxylic acid esters: an approach to γ-amino acids

  摘要：

  Efficient Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to ethyl-gamma-phthalimidocrotonate by using bis-sulfoxide ligand affords gamma-aminobutyric acid (GABA) derivatives with high enantioselectivities (90-96% ee) under mild conditions. Optically pure (S)-Baclofen and (S)-Rolipram have been prepared successfully through this synthetic route. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.12.044

文献信息

• Rh-Catalyzed Asymmetric Hydrogenation of γ-Phthalimido-Substituted α,β-Unsaturated Carboxylic Acid Esters:  An Efficient Enantioselective Synthesis of β-Aryl-γ-amino Acids
  作者：Jun Deng、Zheng-Chao Duan、Jia-Di Huang、Xiang-Ping Hu、Dao-Yong Wang、Sai-Bo Yu、Xue-Feng Xu、Zhuo Zheng

  DOI：10.1021/ol702193v

  日期：2007.11.1

  A series of chiral beta-aryl-gamma-amino acid ester derivatives were synthesized in high enantioselectivities (93-97% ee) via the Rh-catalyzed asymmetric hydrogenation of gamma-phthalimido-alpha,beta-unsaturated carboxylic acid esters using highly modular chiral BoPhoz-type phosphine-aminophosphine ligands. The method has been applied successfully to the synthesis of several chiral pharmaceuticals

  使用高度模块化的手性化合物，通过Rh催化的γ-邻苯二甲酰亚胺-α，β-不饱和羧酸酯的不对称加氢反应，以高对映选择性（93-97％ee）合成了一系列手性β-芳基-γ-氨基酸酯衍生物BoPhoz型膦-氨基膦配体。该方法已成功地用于几种手性药物的合成，包括具有高对映选择性的（R）-巴氯芬和（R）-咯利普兰。
• Enantioselective Synthesis of β-Aryl-γ-amino Acid Derivatives via Cu-Catalyzed Asymmetric 1,4-Reductions of γ-Phthalimido-Substituted α,β-Unsaturated Carboxylic Acid Esters
  作者：Jun Deng、Xiang-Ping Hu、Jia-Di Huang、Sai-Bo Yu、Dao-Yong Wang、Zheng-Chao Duan、Zhuo Zheng

  DOI：10.1021/jo800794p

  日期：2008.8.1

  γ-amino butyric acid derivatives were synthesized in good enantioselectivities via the Cu-catalyzed asymmetric conjugate reduction of γ-phthalimido-α,β-unsaturated carboxylic acid esters using Cu(OAc)2·H2O as a catalyst precursor, (S)-BINAP as a ligand, PMHS as a hydride source, and t-BuOH as an additive. The methodology has been applied successfully to the enantioselective synthesis of a chiral pharmaceutical

  以Cu（OAc）2·H2O为催化剂，通过Cu催化γ-邻苯二甲酰亚胺-α，β-不饱和羧酸酯的不对称共轭还原反应，合成了一系列具有良好对映选择性的手性β-芳基取代的γ-氨基丁酸衍生物。催化剂前体，（S）-BINAP作为配体，PMHS作为氢化物源，t-BuOH作为添加剂。该方法已成功应用于手性药物（R）-baclofen的对映选择性合成。
• Rh-Catalyzed Asymmetric Hydrogenation of γ-Phthalimido-Substituted α,β-Unsaturated Carboxylic Acid Esters: An Efficient Enantioselective Synthesis of β-Aryl-γ-amino Acids
  作者：Jun Deng、Zheng-Chao Duan、Jia-Di Huang、Xiang-Ping Hu、Dao-Yong Wang、Sai-Bo Yu、Xue-Feng Xu、Zhuo Zheng

  DOI：10.1021/ol801179x

  日期：2008.8.7
• Rhodium-catalyzed asymmetric addition of arylboronic acids to γ-phthalimido-substituted-α,β-unsaturated carboxylic acid esters: an approach to γ-amino acids
  作者：Fuzhong Han、Jun Chen、Xiangyang Zhang、Jibing Liu、Linfeng Cun、Jin Zhu、Jingen Deng、Jian Liao

  DOI：10.1016/j.tetlet.2010.12.044

  日期：2011.2

  Efficient Rh-catalyzed asymmetric 1,4-addition of arylboronic acids to ethyl-gamma-phthalimidocrotonate by using bis-sulfoxide ligand affords gamma-aminobutyric acid (GABA) derivatives with high enantioselectivities (90-96% ee) under mild conditions. Optically pure (S)-Baclofen and (S)-Rolipram have been prepared successfully through this synthetic route. (C) 2010 Elsevier Ltd. All rights reserved.