1β-allyl-3,4,4a,5,6,7,8,8a-octahydro-5,5,8aβ-trimethyl-trans-naphthalen-2(1H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1β-allyl-3,4,4a,5,6,7,8,8a-octahydro-5,5,8aβ-trimethyl-trans-naphthalen-2(1H)-one
• 英文别名: (1R,4aS,8aS)-5,5,8a-trimethyl-1-prop-2-enyl-3,4,4a,6,7,8-hexahydro-1H-naphthalen-2-one
• 化学式: C₁₆H₂₆O
• 分子量: 234.382
• InChiKey: GTZYAEYDBIZPMV-DUVNUKRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  1β-allyl-3,4,4a,5,6,7,8,8a-octahydro-5,5,8aβ-trimethyl-trans-naphthalen-2(1H)-one 在 sodium tetrahydroborate 、 对甲苯磺酸 、 臭氧 作用下， 以 乙醚 、 硝基甲烷 为溶剂， 反应 1.75h， 生成 (±)-ambrox
  参考文献：
  名称：

  The Synthesis of RacemicAmbrox®

  摘要：

  Abstract(±)‐Ambrox (10), the racemic form of (−)‐Ambrox®, the commercially most important ambergris odorant has been synthesized from a readily available bicyclic keto ester in five steps. The racemic ether retains the characteristic scent of fine‐quality ambergis, and the odor threshold of the racemate and the (−)‐enantiomer prepared from natural sclareol were found to be essentially identical.

  DOI：

  10.1002/hlca.19890720517
• 作为产物：
  描述：

  (1S,4aR,8aR)-3,4,4a,5,6,7,8,8a-octahydro-1-methoxycarbonyl-5,5,8a-trimethyl-trans-naphthalene-2(1H)-one 在 sodium hydride 、 calcium chloride 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 、 xylene 为溶剂， 反应 6.75h， 生成 1β-allyl-3,4,4a,5,6,7,8,8a-octahydro-5,5,8aβ-trimethyl-trans-naphthalen-2(1H)-one
  参考文献：
  名称：

  The Synthesis of RacemicAmbrox®

  摘要：

  Abstract(±)‐Ambrox (10), the racemic form of (−)‐Ambrox®, the commercially most important ambergris odorant has been synthesized from a readily available bicyclic keto ester in five steps. The racemic ether retains the characteristic scent of fine‐quality ambergis, and the odor threshold of the racemate and the (−)‐enantiomer prepared from natural sclareol were found to be essentially identical.

  DOI：

  10.1002/hlca.19890720517

文献信息

• The Synthesis of Racemic<i>Ambrox</i>®
  作者：George Büchi、Hans Wüest

  DOI：10.1002/hlca.19890720517

  日期：1989.8.9

  Abstract(±)‐Ambrox (10), the racemic form of (−)‐Ambrox®, the commercially most important ambergris odorant has been synthesized from a readily available bicyclic keto ester in five steps. The racemic ether retains the characteristic scent of fine‐quality ambergis, and the odor threshold of the racemate and the (−)‐enantiomer prepared from natural sclareol were found to be essentially identical.