(1R,4S)-1,7,7-Trimethyl-2-propionyl-2-aza-bicyclo[2.2.1]heptan-3-one | 164145-12-4

• 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)-1,7,7-Trimethyl-2-propionyl-2-aza-bicyclo[2.2.1]heptan-3-one
• 英文别名: (1R,4S)-1,7,7-trimethyl-2-propanoyl-2-azabicyclo[2.2.1]heptan-3-one
• CAS: 164145-12-4
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: PVJFMUZIDJOZDH-PRHODGIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  3-溴丙烯 、 (1R,4S)-1,7,7-Trimethyl-2-propionyl-2-aza-bicyclo[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90%的产率得到(1R,4S)-1,7,7-Trimethyl-2-((R)-2-methyl-pent-4-enoyl)-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)-1,7,7-trimethyl-2-azabicyclo<2.2.1>heptan-3-one 以 1,2-二氯乙烷 、 甲苯 、 乙腈 为溶剂， 反应 28.0h， 生成 (1R,4S)-1,7,7-Trimethyl-2-propionyl-2-aza-bicyclo[2.2.1]heptan-3-one
  参考文献：
  名称：

  Facile Preparation and Functionalization of Chiral Stabilized Ylides from Common Chiral Auxiliaries Using Triphenyl- phosphoranylideneketene (the Bestmann Ylide) and Their Use in Wittig Reactions

  摘要：

  Camphor-derived lactams and other related chiral controllers have been found to react with the Bestmann ylide (triphenyl-phosphoranylideneketene) upon heating in toluene. The resulting parent ylides provide convenient access to a structurally diverse set of chiral stabilized ylides via functionalization. The utility of these chiral ylides for Wittig reactions has been briefly investigated and the effects of alpha-substitution noted.

  DOI：

  10.1021/jo061732y

文献信息

• Facile Preparation and Functionalization of Chiral Stabilized Ylides from Common Chiral Auxiliaries Using Triphenyl- phosphoranylideneketene (the Bestmann Ylide) and Their Use in Wittig Reactions
  作者：Robert K. Boeckman,、Xinyi Song、Joseph E. Pero

  DOI：10.1021/jo061732y

  日期：2006.11.1

  Camphor-derived lactams and other related chiral controllers have been found to react with the Bestmann ylide (triphenyl-phosphoranylideneketene) upon heating in toluene. The resulting parent ylides provide convenient access to a structurally diverse set of chiral stabilized ylides via functionalization. The utility of these chiral ylides for Wittig reactions has been briefly investigated and the effects of alpha-substitution noted.
• 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.