6-Cycloundecen-1-one, 2,6,9,9-tetramethyl-, (6E)- | 431078-58-9

• 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: 6-Cycloundecen-1-one, 2,6,9,9-tetramethyl-, (6E)-
• 英文别名: (2RS)-tetrahydrozerumbone；(+/-)-2,6,9,9-tetramethyl-cycloundec-6t-enone；(+/-)-2,6,9,9-Tetramethyl-cycloundec-6t-enon；(+/-)-1.1.4.8-Tetramethyl-cycloundecen-(3t)-on-(9)；Tetrahydro-zerumbon, 2,6,9,9-Tetramethyl-cycloundec-6-en-1-on；6,7,9,10-Tetrahydro-zerumbon；Tetrahydro-zerumbon
• CAS: 431078-58-9
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: NEJOPKLSMVQCNO-XYOKQWHBSA-N

物化性质

• 沸点：
  304.3±31.0 °C(Predicted)
• 密度：
  0.850±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  6-Cycloundecen-1-one, 2,6,9,9-tetramethyl-, (6E)- 在 lithium aluminium tetrahydride 作用下， 生成 tetrahydrozerumbol
  参考文献：
  名称：

  Locomotor-Reducing Effects and Structural Characteristics of Inhaled Zerumbone and Tetrahydrozerumbone Derivatives

  摘要：

  台湾产中药材之泽泻泽姜黄(Zingiber zerumbet SMITH, Zingiberaceae)之根茎中含有一种11员环倍半萜烯化合物泽泻泽姜酮1。在本研究中，我们探讨了泽泻泽姜酮1、α-长蒎烯(2)、四氢泽泻泽姜酮立体异构体(3-5)以及四氢泽泻泽姜酮衍生物(6-9)的结构-活性关系。含氧官能团以及C1和C2的构型对泽泻泽姜酮1及其衍生物2-9的自发性运动活性降低有贡献。

  DOI：

  10.1248/bpb.b14-00314
• 作为产物：
  描述：

  花薑酮 在 Lindlar's catalyst 氢气 作用下， 生成 6-Cycloundecen-1-one, 2,6,9,9-tetramethyl-, (6E)-
  参考文献：
  名称：

  在倍半萜中的研究—XVI：斑仑酮，单环倍半萜烯酮

  摘要：

  已发现先前分配给zerumbone的结构是站不住脚的。酮已显示为含有三个烯键的单环，并且已进一步与腐殖烯相关。臭氧分解的结果和碱催化的裂解使该化合物配制成2,6,9,9-四甲基-2,6,10-环十一碳烯-1-酮。

  DOI：

  10.1016/0040-4020(60)80027-0

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.
• Efficient synthesis of an optically active tetrahydrozerumbone exhibiting a fragrance and the application of zerumbone derivatives with a medium ring structure
  作者：Takashi Kitayama、Ayumi Saito、Sayo Ohta

  DOI：10.1016/j.tetasy.2012.09.016

  日期：2012.11

  (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.
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