(1R,4S)-2-((S)-2,3-Dimethyl-butyryl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one | 379736-62-6

• 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-((S)-2,3-Dimethyl-butyryl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one
• 英文别名: (1R,4S)-2-[(2S)-2,3-dimethylbutanoyl]-1,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 379736-62-6
• 化学式: C₁₅H₂₅NO₂
• 分子量: 251.369
• InChiKey: DPDGUZYJXOKYHO-FIXISWKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙烯酰碘 、 (1R,4S)-2-((S)-2,3-Dimethyl-butyryl)-1,7,7-trimethyl-2-aza-bicyclo[2.2.1]heptan-3-one 在 2,3-萘基二缩醛 作用下， 以 四氢呋喃 为溶剂， 反应 4.67h， 以67%的产率得到(1R,4S)-2-((R)-2-Isopropyl-2-methyl-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)-(3'-methyl butanoyl)-1,7,7,-trimethyl-2-azabicyclo[2.2.1]heptan-3-one 、 碘甲烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 以92%的产率得到(1R,4S)-2-((S)-2,3-Dimethyl-butyryl)-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

文献信息

• Toward the Development of a General Chiral Auxiliary. 9. Highly Diastereoselective Alkylations and Acylations to Form Tertiary and Quaternary Centers
  作者：Robert K. Boeckman,、Debra J. Boehmler、Rhonda A. Musselman

  DOI：10.1021/ol016738i

  日期：2001.11.1

  [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.