1-[(2R,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]ethanone | 78719-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[(2R,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]ethanone
• CAS: 78719-76-3
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: KSYZXXXPANLOBQ-HZSPNIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  甲基锂 、 1-[(2R,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]ethanone 在 盐酸 作用下， 以 乙醚 、 水 为溶剂， 反应 1.0h， 以100%的产率得到r-eudesmol
  参考文献：
  名称：

  Short and efficient hemisynthesis of α-eudesmol and cryptomeridiol

  摘要：

  The aerial part of Dittrichia viscosa yielded two sesquiterpenes, isocostic acid (1) and ilicic acid (2), on multigram scale. These acids are appropriate starting materials for short and facile syntheses of a-eudesmol (5) and cryptomeridiol (6), natural products featuring anti-Alzheimer and anti-spasmodic properties. Compounds 5 and 6 were obtained in three steps in overall yields of 70% and 52%, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.064
• 作为产物：
  描述：

  (+)-Eudesma-3,11(13)-dien-12-oic acid 在 盐酸 、 sodium azide 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 7.0h， 生成 1-[(2R,4aR,8aR)-4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl]ethanone
  参考文献：
  名称：

  Short and efficient hemisynthesis of α-eudesmol and cryptomeridiol

  摘要：

  The aerial part of Dittrichia viscosa yielded two sesquiterpenes, isocostic acid (1) and ilicic acid (2), on multigram scale. These acids are appropriate starting materials for short and facile syntheses of a-eudesmol (5) and cryptomeridiol (6), natural products featuring anti-Alzheimer and anti-spasmodic properties. Compounds 5 and 6 were obtained in three steps in overall yields of 70% and 52%, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.064

文献信息

• The chemistry of thujone. X. Thujone as a chiral synthon for the preparation of sesquiterpenes. Synthesis of (+)-α-eudesmol and (−)-α-selinene
  作者：James P. Kutney、Ashok K. Singh

  DOI：10.1139/v84-239

  日期：1984.8.1

  Efficient synthetic routes to the chiral sesquiterpenes (+)-α-eudesmol (7) and (−)-α-selinene (9) from a thujone-derived intermediate (2) are described.

  描述了从 thujone 衍生的中间体 (2) 到手性倍半萜 (+)-α-eudesmol (7) 和 (-)-α-selinene (9) 的有效合成路线。
• Short and efficient hemisynthesis of α-eudesmol and cryptomeridiol
  作者：Mohamed Tebbaa、Ahmed El Hakmaoui、Ahmed Benharref、Mohamed Akssira

  DOI：10.1016/j.tetlet.2011.05.064

  日期：2011.7

  The aerial part of Dittrichia viscosa yielded two sesquiterpenes, isocostic acid (1) and ilicic acid (2), on multigram scale. These acids are appropriate starting materials for short and facile syntheses of a-eudesmol (5) and cryptomeridiol (6), natural products featuring anti-Alzheimer and anti-spasmodic properties. Compounds 5 and 6 were obtained in three steps in overall yields of 70% and 52%, respectively. (C) 2011 Elsevier Ltd. All rights reserved.