9β-acetoxy-eudesma-4,11-dien-3-one | 174788-49-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9β-acetoxy-eudesma-4,11-dien-3-one
• 英文别名: (+)-9β-acetoxyeudesma-4,11(12)-dien-3-one；[(1S,3S,8aS)-5,8a-dimethyl-6-oxo-3-prop-1-en-2-yl-1,2,3,4,7,8-hexahydronaphthalen-1-yl] acetate
• CAS: 174788-49-9
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: MUDJCBQOPUJRRI-JQFCIGGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9β-acetoxy-eudesma-4,11-dien-3-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 47.0h， 以75%的产率得到Acetic acid (1S,3S,8aS)-3-isopropenyl-5,8a-dimethyl-6-oxo-1,2,3,4,6,8a-hexahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Studies on the Dehydrogenation of 9-Oxygenated-eudesma-4-en-3-ones with DDQ

  摘要：

  9-Acetoxy-eudesma-4,11-dien-3-ones (4a, 4b) and 9-acetoxy-14-noreudesma-4,11-dien-3-ones (5a, 5b) were treated with DDQ in dioxane to yield normal 1,2-dehydro-products, whereas 14-noreudesma-4,11-dien-3,9-diones (2a, 2b) afforded a rearranged aromatic product, 1-hydroxy-15-noreudesma-1, 3, 5 (10), 11-tetraen-9-one (3). No reaction was observed by treatment of eudesma-4,11-dien-3,9-diones (1a, 1b) with DDQ under the same conditions. The effect of 10-methyl configuration on this reaction is also discussed.

  DOI：

  10.1080/00397919608003648
• 作为产物：
  描述：

  eudesma-4,11-dien-3,9-dione 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 9β-acetoxy-eudesma-4,11-dien-3-one
  参考文献：
  名称：

  Studies on the Dehydrogenation of 9-Oxygenated-eudesma-4-en-3-ones with DDQ

  摘要：

  9-Acetoxy-eudesma-4,11-dien-3-ones (4a, 4b) and 9-acetoxy-14-noreudesma-4,11-dien-3-ones (5a, 5b) were treated with DDQ in dioxane to yield normal 1,2-dehydro-products, whereas 14-noreudesma-4,11-dien-3,9-diones (2a, 2b) afforded a rearranged aromatic product, 1-hydroxy-15-noreudesma-1, 3, 5 (10), 11-tetraen-9-one (3). No reaction was observed by treatment of eudesma-4,11-dien-3,9-diones (1a, 1b) with DDQ under the same conditions. The effect of 10-methyl configuration on this reaction is also discussed.

  DOI：

  10.1080/00397919608003648

文献信息

• The Enantioselective Synthesis of (+)-Selina-3, 11-Dien-9-ol
  作者：Jiong Yang、Zhaoming Xiong、Yonggang Chen、Yulin Li

  DOI：10.1080/00397919708005005

  日期：1997.9

  The title compound 1 was enantioselectively synthesized from oxycarvone in nine steps with an overall yield of 15%. The key step involves the p-toluenesulfonhydrazide assisted diastereoselective reductive rearrangement of allylic alcohol.