benzyl 2,4,10-trioxaadamant-3-yl ketone | 1392441-55-2

• 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: benzyl 2,4,10-trioxaadamant-3-yl ketone
• 英文别名: 2-Phenyl-1-(2,4,10-trioxatricyclo[3.3.1.13,7]decan-3-yl)ethanone
• CAS: 1392441-55-2
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: VOMDLSGZVPXBKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2,4,10-trioxaadamant-3-yl ketone 在 甲醇 、 sodium tetrahydroborate 、 20 % Pd(OH)2/C 、 氢气 、 四氯化钛 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 20.0 ℃ 、405.33 kPa 条件下， 反应 29.0h， 生成 (S)-1-(2,4,10-trioxaadamant-3-yl)-2-phenylethylamine
  参考文献：
  名称：

  An approach to chiral amino acids via reductive amination of ketones: hydride reduction of 1-(S)-phenethyl amine derived Schiff bases of C-protected α-keto acids

  摘要：

  Various 1-acyl-2,4,10-trioxaadamantanes were prepared from the corresponding 1-methoxycarbonyl derivatives, via conversion to the N-acylpiperidine derivatives followed by reaction with a Grignard reagent in refluxing THF. These alpha-keto orthoformates were converted to the corresponding imines with 1-(S)-phenethyl amine (TiCl4/Et3N/toluene/reflux), with the Schiff bases being reduced further with NaBH4 (MeOH/0 degrees C) into the corresponding 1-(S)-phenethyl amines (diastereomeric excess 91:9 by NMR). Hydrogenolysis of the phenethyl group (Pd-C/MeOH) finally led to the 1-(aminoalkyl)trioxaadamantanes, which are chiral C-protected alpha-amino acids, in excellent overall yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.017
• 作为产物：
  描述：

  Methyl 2,4,10-trioxatricyclo[3.3.1.13,7]decane-3-carboxylate 在 碘 、 magnesium 、 magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 15.83h， 生成 benzyl 2,4,10-trioxaadamant-3-yl ketone
  参考文献：
  名称：

  An approach to chiral amino acids via reductive amination of ketones: hydride reduction of 1-(S)-phenethyl amine derived Schiff bases of C-protected α-keto acids

  摘要：

  Various 1-acyl-2,4,10-trioxaadamantanes were prepared from the corresponding 1-methoxycarbonyl derivatives, via conversion to the N-acylpiperidine derivatives followed by reaction with a Grignard reagent in refluxing THF. These alpha-keto orthoformates were converted to the corresponding imines with 1-(S)-phenethyl amine (TiCl4/Et3N/toluene/reflux), with the Schiff bases being reduced further with NaBH4 (MeOH/0 degrees C) into the corresponding 1-(S)-phenethyl amines (diastereomeric excess 91:9 by NMR). Hydrogenolysis of the phenethyl group (Pd-C/MeOH) finally led to the 1-(aminoalkyl)trioxaadamantanes, which are chiral C-protected alpha-amino acids, in excellent overall yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.06.017