(1R,4S)-2-(2-Benzyloxy-acetyl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one | 379736-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (1R,4S)-2-(2-Benzyloxy-acetyl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one
• 英文别名: (1R,4S)-1,7,7-trimethyl-2-(2-phenylmethoxyacetyl)-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 379736-69-3
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: RUOHRYPTDKSINP-RDTXWAMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙烯酰碘 、 (1R,4S)-2-(2-Benzyloxy-acetyl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (1R)-1,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one 、 (1R,4S)-2-((S)-2-Benzyloxy-pent-4-enoyl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one 、 (1R,4S)-2-((R)-2-Benzyloxy-pent-4-enoyl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Toward the Development of a General Chiral Auxiliary. 9. Highly Diastereoselective Alkylations and Acylations to Form Tertiary and Quaternary Centers

  摘要：

  [GRAPHICS]Enolates of a new camphor-derived lactam auxiliary are shown to monoalkylate with very high diastereoselectivity. A second alkylation occurs with reactive alkylating agents to afford quaternary centers also with high diastereoselectivity, In accord with a proposed model for diastereoselection, lithium and sodium enolates provide products with an opposite sense of asymmetric induction.

  DOI：

  10.1021/ol016738i
• 作为产物：
  描述：

  (1R,4S)-2-(2-Isopropyl-2-methyl-pent-4-enoyl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one 以 四氢呋喃 为溶剂， 生成 (1R,4S)-2-(2-Benzyloxy-acetyl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Toward the Development of a General Chiral Auxiliary. 9. Highly Diastereoselective Alkylations and Acylations to Form Tertiary and Quaternary Centers

  摘要：

  [GRAPHICS]Enolates of a new camphor-derived lactam auxiliary are shown to monoalkylate with very high diastereoselectivity. A second alkylation occurs with reactive alkylating agents to afford quaternary centers also with high diastereoselectivity, In accord with a proposed model for diastereoselection, lithium and sodium enolates provide products with an opposite sense of asymmetric induction.

  DOI：

  10.1021/ol016738i