(R)-2-Ethyl-1-((1R,4S)-1,7,7-trimethyl-3-oxo-2-aza-bicyclo[2.2.1]hept-2-yl)-pentane-1,3-dione | 1027043-97-5

• 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: (R)-2-Ethyl-1-((1R,4S)-1,7,7-trimethyl-3-oxo-2-aza-bicyclo[2.2.1]hept-2-yl)-pentane-1,3-dione
• 英文别名: (2R)-2-ethyl-1-[(1R,4S)-1,7,7-trimethyl-3-oxo-2-azabicyclo[2.2.1]heptan-2-yl]pentane-1,3-dione
• CAS: 1027043-97-5
• 化学式: C₁₆H₂₅NO₃
• 分子量: 279.379
• InChiKey: SACFTWFMFUCUCH-GLKRBJQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54.4
• 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 、 (R)-2-Ethyl-1-((1R,4S)-1,7,7-trimethyl-3-oxo-2-aza-bicyclo[2.2.1]hept-2-yl)-pentane-1,3-dione 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(R)-2-Allyl-2-ethyl-1-((1R,4S)-1,7,7-trimethyl-3-oxo-2-aza-bicyclo[2.2.1]hept-2-yl)-pentane-1,3-dione
  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：

  丙酰氯 、 (1R,4S)-2-butanoyl-1,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 以68%的产率得到(R)-2-Ethyl-1-((1R,4S)-1,7,7-trimethyl-3-oxo-2-aza-bicyclo[2.2.1]hept-2-yl)-pentane-1,3-dione
  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.