[1-(2-Hydroxynaphthalen-1-yl)naphthalen-2-yl] 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate | 180311-13-1

• 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: [1-(2-Hydroxynaphthalen-1-yl)naphthalen-2-yl] 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 180311-13-1
• 化学式: C₂₇H₂₅NO₅
• 分子量: 443.499
• InChiKey: VFEFSNLKCPEXDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [1-(2-Hydroxynaphthalen-1-yl)naphthalen-2-yl] 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate 在 盐酸 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 7.7h， 生成 [1-[2-(2-Benzamido-3-cyanopropanoyl)oxynaphthalen-1-yl]naphthalen-2-yl] benzoate
  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：

  BOC-甘氨酸 、 S-1,1'-联-2-萘酚 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到[1-(2-Hydroxynaphthalen-1-yl)naphthalen-2-yl] 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
  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

文献信息

• Asymmetric synthesis of uncommon α-amino acids by diastereoselective alkylations of a chiral glycine equivalent
  作者：Kiyoshi Tanaka、Mija Ahn、Yukari Watanabe、Kaoru Fuji

  DOI：10.1016/0957-4166(96)00212-1

  日期：1996.6

  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