1-[(1R,2R,3S,4S)-3-acetyl-2-bicyclo[2.2.1]hept-5-enyl]ethanone | 173006-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(1R,2R,3S,4S)-3-acetyl-2-bicyclo[2.2.1]hept-5-enyl]ethanone
• CAS: 173006-06-9
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: YCSALOMWYSBYOX-CKIJPRSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(1R,2R,3S,4S)-3-acetyl-2-bicyclo[2.2.1]hept-5-enyl]ethanone 在 二甲基硫 、 臭氧 作用下， 生成 (1S,3R,4S,5R)-4,5-Diacetyl-cyclopentane-1,3-dicarbaldehyde
  参考文献：
  名称：

  Novel Oxa-Cage Compounds: Synthesis, Structures, and the Formation Mechanism of Tetraacetal Oxa-Cages and Convex Tetraquinane Oxa-Cages

  摘要：

  Several novel tetraacetal era-cage compounds 5a-d and convex tetraquinane era-cage compounds 16a-d and 17b-d are synthesized from alkylfurans in three steps. Ozonolysis of the cis-endo-1,4-diones 3a-d in dichloromethane at -78 degrees C followed by reduction with dimethyl sulfide gives the era-cages 5a-d in high yields, respectively. The structures of these new tetraacetal era-cages are deduced from their spectral data and proven for the first time by X-ray analysis of the crystalline compound 5a. Ozonolysis of 3a-d in dichloromethane at -78 degrees C followed by treatment with triethylamine gives the convex tetraquinane era-cages 16a-d and 17b-d in 85-90% yields, respectively. The structures of these novel convex tetraquinane era-cages are finally proven by X-ray analysis of the crystalline compound 16a. Two reaction mechanisms via the common final ozonides are proposed for the formation of these two different types of era-cage compounds. The structures of the final ozonides formed by ozonolysis of the norbornene derivatives 3 are deduced to be 9 with endo stereochemistry on the basis of their spectral data and the formation of these two types of era-cages from the final ozonides. In reaction with the final ozonides, triethylamine is found to act as a base instead of a reducing agent, a different function from that of dimethyl sulfide. The synthesis of era-cages 24 and 25, which possess aromatic substituents directly on the skeleton, has also been accomplished.

  DOI：

  10.1021/jo00128a031
• 作为产物：
  描述：

  2,5-二氢-2,5-二甲氧基-2,5-二甲基呋喃 在 溶剂黄146 作用下， 生成 1-[(1R,2R,3S,4S)-3-acetyl-2-bicyclo[2.2.1]hept-5-enyl]ethanone
  参考文献：
  名称：

  Aminos�uren, 9. Mitt.: Farbreaktionen mit cyclischen Di- und Triacetylverbindungen

  摘要：

  DOI：

  10.1007/bf00904452

文献信息

• Novel Oxa-Cage Compounds: Synthesis, Structures, and the Formation Mechanism of Tetraacetal Oxa-Cages and Convex Tetraquinane Oxa-Cages
  作者：Hsien-Jen Wu、Chu-Chung Lin

  DOI：10.1021/jo00128a031

  日期：1995.11

  Several novel tetraacetal era-cage compounds 5a-d and convex tetraquinane era-cage compounds 16a-d and 17b-d are synthesized from alkylfurans in three steps. Ozonolysis of the cis-endo-1,4-diones 3a-d in dichloromethane at -78 degrees C followed by reduction with dimethyl sulfide gives the era-cages 5a-d in high yields, respectively. The structures of these new tetraacetal era-cages are deduced from their spectral data and proven for the first time by X-ray analysis of the crystalline compound 5a. Ozonolysis of 3a-d in dichloromethane at -78 degrees C followed by treatment with triethylamine gives the convex tetraquinane era-cages 16a-d and 17b-d in 85-90% yields, respectively. The structures of these novel convex tetraquinane era-cages are finally proven by X-ray analysis of the crystalline compound 16a. Two reaction mechanisms via the common final ozonides are proposed for the formation of these two different types of era-cage compounds. The structures of the final ozonides formed by ozonolysis of the norbornene derivatives 3 are deduced to be 9 with endo stereochemistry on the basis of their spectral data and the formation of these two types of era-cages from the final ozonides. In reaction with the final ozonides, triethylamine is found to act as a base instead of a reducing agent, a different function from that of dimethyl sulfide. The synthesis of era-cages 24 and 25, which possess aromatic substituents directly on the skeleton, has also been accomplished.
• Aminos�uren, 9. Mitt.: Farbreaktionen mit cyclischen Di- und Triacetylverbindungen
  作者：R. Riemschneider、P. Claus

  DOI：10.1007/bf00904452

  日期：——