tert-butyl N-[(2S)-1-[(3aR,8bS)-2,2-dimethyl-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate | 190059-40-6

• 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 N-[(2S)-1-[(3aR,8bS)-2,2-dimethyl-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 190059-40-6
• 化学式: C₂₆H₃₂N₂O₄
• 分子量: 436.551
• InChiKey: YXNDJSPYDUQAFG-BDTNDASRSA-N

物化性质

• 沸点：
  613.4±55.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[(3aR,8bS)-2,2-dimethyl-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate 在 盐酸 作用下， 以86.1%的产率得到L-苯丙氨酸
  参考文献：
  名称：

  Asymmetric synthesis of α-amino acid derivatives via an electrophilic amination of chiral amide cuprates with Li t-butyl-N-tosyloxycarbamate

  摘要：

  The utility of lithium t-butyl-N-tosyloxycarbamate (LiBTOC) as a (+)NHBOC synthon in highly diastereoselective reactions with chiral cis-aminoindanol derived amide cuprates is described. The diastereoselectivities of these reactions ranged from 96% to greater than 99%. The subsequent transformation of these adducts to alpha-amino acids ir also described (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00477-2
• 作为产物：
  描述：

  (1S,2R)-(-)-1-氨基-2-茚醇 在 正丁基锂 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 tert-butyl N-[(2S)-1-[(3aR,8bS)-2,2-dimethyl-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-1-yl]-1-oxo-3-phenylpropan-2-yl]carbamate
  参考文献：
  名称：

  Asymmetric synthesis of α-amino acid derivatives via an electrophilic amination of chiral amide cuprates with Li t-butyl-N-tosyloxycarbamate

  摘要：

  The utility of lithium t-butyl-N-tosyloxycarbamate (LiBTOC) as a (+)NHBOC synthon in highly diastereoselective reactions with chiral cis-aminoindanol derived amide cuprates is described. The diastereoselectivities of these reactions ranged from 96% to greater than 99%. The subsequent transformation of these adducts to alpha-amino acids ir also described (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00477-2

文献信息

• Asymmetric synthesis of α-amino acid derivatives via an electrophilic amination of chiral amide cuprates with Li t-butyl-N-tosyloxycarbamate
  作者：Nan Zheng、Joseph D. Armstrong、J.Christopher McWilliams、R.P. Volante

  DOI：10.1016/s0040-4039(97)00477-2

  日期：1997.4

  The utility of lithium t-butyl-N-tosyloxycarbamate (LiBTOC) as a (+)NHBOC synthon in highly diastereoselective reactions with chiral cis-aminoindanol derived amide cuprates is described. The diastereoselectivities of these reactions ranged from 96% to greater than 99%. The subsequent transformation of these adducts to alpha-amino acids ir also described (C) 1997 Elsevier Science Ltd.