(1R,5R,10S)-2-oxo-5-phenyl-6-aza-3-oxatricyclo[8.3.0.0^1,6]tridecane | 1231765-99-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (1R,5R,10S)-2-oxo-5-phenyl-6-aza-3-oxatricyclo[8.3.0.0^1,6]tridecane
• CAS: 1231765-99-3
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: YKMGUZOJSWVFNS-YQQAZPJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1R,5R,10S)-2-oxo-5-phenyl-6-aza-3-oxatricyclo[8.3.0.0^1,6]tridecane 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以94%的产率得到(4aS,7aR)-octahydro-1H-cyclopenta[b]pyridine-7a-carboxylic acid
  参考文献：
  名称：

  Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids

  摘要：

  Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.

  DOI：

  10.1021/ol1010246
• 作为产物：
  描述：

  (1R,5R,10S)-2,7-dioxo-5-phenyl-6-aza-3-oxatricyclo[8.3.0.0^1,6]tridec-8-ene 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以33%的产率得到(1R,5R,10S)-2-oxo-5-phenyl-6-aza-3-oxatricyclo[8.3.0.0^1,6]tridecane
  参考文献：
  名称：

  Diastereoselective Intramolecular Additions of Allyl- and Propargylsilanes to Iminium Ions: Synthesis of Cyclic and Bicyclic Quaternary Amino Acids

  摘要：

  Chiral imino lactones derived from (R)-phenylglycinol containing an allyl- or propargyltrimethylsilyl group in the side chain readily cyclized in the presence of acidic reagents to afford spirocyclic compounds with high diastereoselectivity. Removal of the chiral auxiliary produced 2-substituted 1-aminocycloalkanecarboxylic acids, whereas further cyclizations by means of metathesis or hydroamination reactions led to bicyclic derivatives of pipecolic acid and proline.

  DOI：

  10.1021/ol1010246