tert-butyl (4S,5S,1'S)-5-(1'-cyanohydroxymethyl)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate | 736151-95-4

• 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: tert-butyl (4S,5S,1'S)-5-(1'-cyanohydroxymethyl)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate
• 英文别名: tert-butyl (4S,5S)-5-[(S)-cyano(hydroxy)methyl]-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate
• CAS: 736151-95-4
• 化学式: C₁₇H₂₁N₃O₅
• 分子量: 347.371
• InChiKey: XMYUMGMTWFTQDK-HZSPNIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (4S,5S,1'S)-5-(1'-cyanohydroxymethyl)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate 在 platinum(IV) oxide 甲酸 、 氢气 、 溶剂黄146 、 sodium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成 (3aS,7R,7aS)-7-Hydroxy-5-(4-methoxy-benzyl)-1-(4-methoxy-phenyl)-hexahydro-imidazo[4,5-c]pyridine-2,4-dione
  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：

  N-二苯亚甲基-甘氨酸叔丁酯 在 sodium hydroxide 、 (R,R)-3,4,5-F₃-C₆H₂-NAS-Br 、 二异丁基氢化铝 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 、 均三甲苯 为溶剂， 反应 15.0h， 生成 tert-butyl (4S,5S,1'S)-5-(1'-cyanohydroxymethyl)-1-(4-methoxyphenyl)-2-oxoimidazolidine-4-carboxylate
  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.