1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[(1R,2S)-1,2]-oxazol-3-yl)-2-phenylethanone | 190059-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[(1R,2S)-1,2]-oxazol-3-yl)-2-phenylethanone
• 英文别名: 1-[(3aR,8bS)-2,2-dimethyl-4,8b-dihydro-3aH-indeno[1,2-d][1,3]oxazol-1-yl]-2-phenylethanone
• CAS: 190059-35-9
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: VZXGDMNBMQNPCR-MJGOQNOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[(1R,2S)-1,2]-oxazol-3-yl)-2-phenylethanone 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 生成 左旋苯甘氨酸
  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 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 生成 1-(2,2-dimethyl-8,8a-dihydro-3aH-indeno[(1R,2S)-1,2]-oxazol-3-yl)-2-phenylethanone
  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

• Pseudoephedrine as a Chiral Auxiliary for Asymmetric Michael Reactions:  Synthesis of 3-Aryl-δ-lactones
  作者：Jacqueline H. Smitrovich、Geneviève N. Boice、Chuanxing Qu、Lisa DiMichele、Todd D. Nelson、Mark A. Huffman、Jerry Murry、James McNamara、Paul J. Reider

  DOI：10.1021/ol0259847

  日期：2002.5.1

  [reaction: see text] The asymmetric Michael reaction of pseudoephedrine amides is reported. The 1,5-dicarbonyl products are converted to 3-aryl-delta-lactones in a two-step reduction/lactonization sequence. This method provides access to enantiomerically enriched trans-3,4-disubstituted delta-lactones.

  [反应：见正文]报道了伪麻黄碱酰胺的不对称迈克尔反应。1，5-二羰基产物按两步还原/内酯化顺序转化为3-芳基-δ-内酯。该方法提供了对映体富集的反式3，4-二取代的δ-内酯的途径。