(1S,2S)-1-acetoxy-2,6,9,9-tetramethyl-6-cycloundecene | 1220702-42-0

• 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: (1S,2S)-1-acetoxy-2,6,9,9-tetramethyl-6-cycloundecene
• 英文别名: [(1S,2S,6E)-2,6,9,9-tetramethylcycloundec-6-en-1-yl] acetate
• CAS: 1220702-42-0
• 化学式: C₁₇H₃₀O₂
• 分子量: 266.424
• InChiKey: PNGINHPSKSACAE-OOFRTQJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  6-Cycloundecen-1-one, 2,6,9,9-tetramethyl-, (6E)- 在 lithium aluminium tetrahydride 、 MeitoQLM lipase 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 35.0 ℃ 、13.33 Pa 条件下， 反应 24.5h， 生成 (1R,2R)-2,6,9,9-tetramethylcycloundeca-6-enol 、 (1S,2S)-1-acetoxy-2,6,9,9-tetramethyl-6-cycloundecene
  参考文献：
  名称：

  Efficient synthesis of an optically active tetrahydrozerumbone exhibiting a fragrance and the application of zerumbone derivatives with a medium ring structure

  摘要：

  (R)-Tetrahydrozerumbone 2, which has a powerful balmy fragrance, contains a stereogenic carbon at the C2 position and can be easily prepared from zerumbone 1, one of the most important materials displaying an NMRDOS character. The reduction of 2 gave two diastereomers of tetrahydrozerumbol 3, and the optically active (>99%ee) alcohols were obtained by a lipase-catalyzed stereoselective transesterification of each racemic alcohol. A barrier to this development is a long reaction time (about four weeks) and the need to separate the diastereoisomers. The desired (2R)-form of 3 was efficiently obtained by a lipase-catalyzed transesterification under optimized conditions using a diastereomeric mixture of racemic 3 as the starting material without separation of the diastereomers. Using this method, the reaction of other zerumbone derivatives is greatly improved. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.09.016

文献信息

• Synthesis of optically active tetrahydrozerumbone
  作者：Takashi Kitayama、Sayo Ohta、Yasushi Kawai、Tomoyasu Nakayama、Masataka Awata

  DOI：10.1016/j.tetasy.2009.11.030

  日期：2010.1

  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.