(E)-3-[(1-tert-Butylcarbamoyl-2-methyl-propyl)-methyl-amino]-acrylic acid methyl ester | 665054-67-1

• 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: (E)-3-[(1-tert-Butylcarbamoyl-2-methyl-propyl)-methyl-amino]-acrylic acid methyl ester
• 英文别名: methyl (E)-3-[[1-(tert-butylamino)-3-methyl-1-oxobutan-2-yl]-methylamino]prop-2-enoate
• CAS: 665054-67-1
• 化学式: C₁₄H₂₆N₂O₃
• 分子量: 270.372
• InChiKey: GTIDICRJFDDLAT-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-[(1-tert-Butylcarbamoyl-2-methyl-propyl)-methyl-amino]-acrylic acid methyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 以90%的产率得到N-tert-Butyl-3-methyl-2-methylamino-butyramide; hydrochloride
  参考文献：
  名称：

  U-4C-3CR versus U-5C-4CR and stereochemical outcomes using suitable bicyclic β-amino acid derivatives as bifunctional components in the Ugi reaction

  摘要：

  Intramolecular Ugi reactions with bicyclic beta-amino acids have been performed and the effects of the configuration and N-alkylation have been studied. We have proven that preferential ring contraction or nucleophilic attack by the solvent depend not only on the presence of N-alkylation but also on the relative disposition of the carboxyl group and the amine. Excellent results in terms of stereoselectivity have been obtained in the case of N-alkyl-3-exo-amino-7-oxabicyclo[2.2.1]-2-endo-carboxylic acids. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.193
• 作为产物：
  描述：

  (1R,2R,3R,4S)-3-[(1-tert-Butylcarbamoyl-2-methyl-propyl)-methyl-amino]-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 以 甲苯 为溶剂， 以95%的产率得到(E)-3-[(1-tert-Butylcarbamoyl-2-methyl-propyl)-methyl-amino]-acrylic acid methyl ester
  参考文献：
  名称：

  U-4C-3CR versus U-5C-4CR and stereochemical outcomes using suitable bicyclic β-amino acid derivatives as bifunctional components in the Ugi reaction

  摘要：

  Intramolecular Ugi reactions with bicyclic beta-amino acids have been performed and the effects of the configuration and N-alkylation have been studied. We have proven that preferential ring contraction or nucleophilic attack by the solvent depend not only on the presence of N-alkylation but also on the relative disposition of the carboxyl group and the amine. Excellent results in terms of stereoselectivity have been obtained in the case of N-alkyl-3-exo-amino-7-oxabicyclo[2.2.1]-2-endo-carboxylic acids. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.193