(1R,2S)-2,6,9,9-tetramethylcycloundec-6-enol | 1220702-53-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S)-2,6,9,9-tetramethylcycloundec-6-enol
• 英文别名: (1R,2S,6E)-2,6,9,9-tetramethylcycloundec-6-en-1-ol
• CAS: 1220702-53-3
• 化学式: C₁₅H₂₈O
• 分子量: 224.387
• InChiKey: WGEMYKLCKPJEQG-AMNUONFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2S)-2,6,9,9-tetramethylcycloundec-6-enol 在 戴斯-马丁氧化剂 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以68%的产率得到(+)-(2S,6E)-2,6,9,9-tetramethyl-6-cycloundecen-1-one
  参考文献：
  名称：

  Synthesis of optically active tetrahydrozerumbone

  摘要：

  Tetra hydrozerumbone 2, which has a powerful balmy fragrance, has a stereogenic carbon at C2 and can be easily prepared from zerumbone 1, which is one of the most important materials that displays ail NMRDOS character. Reduction of 2 gave two diastereomers 3 and 4: their optically active (>99% ee) alcohols were obtained by lipase-catalyzed stereoselective transesterification of each racemic alcohol. The enantioselectivity of tetrahydrozerumbol does not entirely depend on the hydroxyl position but on the 2-methyl position Compounds (R)-2 and (S)-2 were obtained by Dess- Martin oxidation of the corresponding alcohols. Interestingly, (R)-2 showed a strong balmy fragrance while (S)-2 had hardly any fragrance (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.030
• 作为产物：
  描述：

  (1R,2S)-1-acetoxy-2,6,9,9-tetramethyl-6-cycloundecene 在 水 、 sodium hydroxide 、 戴斯-马丁氧化剂 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以97%的产率得到(1R,2S)-2,6,9,9-tetramethylcycloundec-6-enol
  参考文献：
  名称：

  Synthesis of optically active tetrahydrozerumbone

  摘要：

  Tetra hydrozerumbone 2, which has a powerful balmy fragrance, has a stereogenic carbon at C2 and can be easily prepared from zerumbone 1, which is one of the most important materials that displays ail NMRDOS character. Reduction of 2 gave two diastereomers 3 and 4: their optically active (>99% ee) alcohols were obtained by lipase-catalyzed stereoselective transesterification of each racemic alcohol. The enantioselectivity of tetrahydrozerumbol does not entirely depend on the hydroxyl position but on the 2-methyl position Compounds (R)-2 and (S)-2 were obtained by Dess- Martin oxidation of the corresponding alcohols. Interestingly, (R)-2 showed a strong balmy fragrance while (S)-2 had hardly any fragrance (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.030