2-(Benzhydrylidene-amino)-pent-4-enoic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester | 180311-18-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 2-(Benzhydrylidene-amino)-pent-4-enoic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester
• CAS: 180311-18-6
• 化学式: C₃₈H₂₉NO₃
• 分子量: 547.653
• InChiKey: YUPGKZSLNRQCLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.75
• 重原子数：
  42.0
• 可旋转键数：
  8.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  58.89
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(Benzhydrylidene-amino)-pent-4-enoic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester 在 盐酸 、 氢氧化钾 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (2S)-methyl 2-N-benzoylaminopent-4-enoate
  参考文献：
  名称：

  Asymmetric synthesis of uncommon α-amino acids by diastereoselective alkylations of a chiral glycine equivalent

  摘要：

  For the purpose of practical preparations of a variety of enantiomerically pure uncommon alpha-amino acids, alkylations of the chiral glycine equivalent 5, which possesses axially chiral binaphthol as an auxiliary, with several electrophiles were investigated. The alkylation proceeded smoothly in satisfactory chemical yield with high diastereoselectivities to give protected alpha-amino acid derivatives. The free hydroxyl group of the auxiliary played an important role for the induction of diastereoselectivity. Using (S)-1,1'-binaphthalene-2,2'-diol as a chiral auxiliary, D-alpha-amino acid derivatives having the unnatural (R)-configuration were predominantly obtained. Some of the alkylated products were converted into free non-proteinogenic D-alpha-amino acids. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00212-1
• 作为产物：
  描述：

  二苯甲酮亚胺 在 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-(Benzhydrylidene-amino)-pent-4-enoic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester
  参考文献：
  名称：

  Asymmetric synthesis of uncommon α-amino acids by diastereoselective alkylations of a chiral glycine equivalent

  摘要：

  For the purpose of practical preparations of a variety of enantiomerically pure uncommon alpha-amino acids, alkylations of the chiral glycine equivalent 5, which possesses axially chiral binaphthol as an auxiliary, with several electrophiles were investigated. The alkylation proceeded smoothly in satisfactory chemical yield with high diastereoselectivities to give protected alpha-amino acid derivatives. The free hydroxyl group of the auxiliary played an important role for the induction of diastereoselectivity. Using (S)-1,1'-binaphthalene-2,2'-diol as a chiral auxiliary, D-alpha-amino acid derivatives having the unnatural (R)-configuration were predominantly obtained. Some of the alkylated products were converted into free non-proteinogenic D-alpha-amino acids. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00212-1