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

• Studies in sesquiterpenes—XVI
  作者：Sukh Dev

  DOI：10.1016/0040-4020(60)80027-0

  日期：1960.1

  The structure, previously assigned to zerumbone, has been found to be untenable. The ketone has been shown to be monocyclic containing three ethylenic linkages, and has been further correlated with humulene. Results from ozonolysis, and base-catalysed cleavage allowed the compound to be formulated as 2,6,9,9-tetramethyl-2,6,10-cyclo-undecatrien-1-one.

  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。
• 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.
• Varier, Proceedings - Indian Academy of Sciences, Section A, 1944, vol. <A> 20, p. 257,260
  作者：Varier

  DOI：——

  日期：——
• van Veen, Recueil des Travaux Chimiques des Pays-Bas, 1939, vol. 58, p. 691,692
  作者：van Veen

  DOI：——

  日期：——