4-tert-butyl 5-ethyl (4S,5S)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4,5-dicarboxylate | 736151-93-2

• 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: 4-tert-butyl 5-ethyl (4S,5S)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4,5-dicarboxylate
• 英文别名: 4-O-tert-butyl 5-O-ethyl (4S,5S)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4,5-dicarboxylate
• CAS: 736151-93-2
• 化学式: C₁₈H₂₄N₂O₆
• 分子量: 364.398
• InChiKey: GAOQOOUPDFQHQB-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-tert-butyl 5-ethyl (4S,5S)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4,5-dicarboxylate 在 platinum(IV) oxide 4-二甲氨基吡啶 、 甲酸 、 氢气 、 二异丁基氢化铝 、 溶剂黄146 、 sodium sulfate 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 47.0h， 生成 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3aS,7R,7aS)-5-(4-methoxy-benzyl)-1-(4-methoxy-phenyl)-2,4-dioxo-octahydro-imidazo[4,5-c]pyridin-7-yl ester
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of a Nitrogen Analogue of Dialkyl Tartrate by Direct Mannich Reaction under Phase-Transfer Conditions

  摘要：

  Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.

  DOI：

  10.1021/ol049215u
• 作为产物：
  描述：

  三光气 、 N-二苯亚甲基-甘氨酸叔丁酯 、 Acetic acid, [(4-methoxyphenyl)imino]-, ethyl ester, (2E)- 在 sodium hydroxide 、 (R,R)-3,4,5-F₃-C₆H₂-NAS-Br 、 三乙胺 作用下， 以 均三甲苯 、 二氯甲烷 为溶剂， 反应 7.0h， 以1.04 g的产率得到4-tert-butyl 5-ethyl (4S,5S)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4,5-dicarboxylate
  参考文献：
  名称：

  Catalytic Asymmetric Synthesis of a Nitrogen Analogue of Dialkyl Tartrate by Direct Mannich Reaction under Phase-Transfer Conditions

  摘要：

  Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.

  DOI：

  10.1021/ol049215u

文献信息

• Catalytic Asymmetric Synthesis of a Nitrogen Analogue of Dialkyl Tartrate by Direct Mannich Reaction under Phase-Transfer Conditions
  作者：Takashi Ooi、Minoru Kameda、Jun-ichi Fujii、Keiji Maruoka

  DOI：10.1021/ol049215u

  日期：2004.7.1

  Phase-transfer-catalyzed direct Mannich reaction of glycinate Schiff base 3 with alpha-imino ester 4 has been accomplished with high enantioselectivity by the utilization of N-spiro C-2-symmetric chiral quaternary ammonium bromide 2 as a catalyst. This methodology enables the catalytic asymmetric synthesis of differentially protected 3-aminoaspartate, a nitrogen analogue of dialkyl tartrate. The product (syn-5) was converted into a precursor (6) of streptolidine lactam.