(+/-)-β-Vetivon | 22196-46-9

• 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: (+/-)-β-Vetivon
• 英文别名: (+/-)-β-vetivone；(5S,6S)-6,10-dimethyl-3-propan-2-ylidenespiro[4.5]dec-9-en-8-one
• CAS: 22196-46-9
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: ISLOGSAEQNKPGG-SWLSCSKDSA-N

物化性质

• 熔点：
  44-46 °C
• 沸点：
  329.5±42.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  (+/-)-β-Vetivon 生成 Spiro[4.5]decan-8-one, 6,10-dimethyl-2-(1-methylethylidene)-
  参考文献：
  名称：

  Structure and synthesis of .beta.-vetivone

  摘要：

  DOI：

  10.1021/jo00826a041
• 作为产物：
  描述：

  二乙基异亚丙基琥珀酸酯 在 lithium triethoxyaluminum hydride 作用下， 生成 (+/-)-β-Vetivon
  参考文献：
  名称：

  Spiroannelation of enol ethers of cyclic 1,3-diketones. Simple stereospecific synthesis of .beta.-vetivone

  摘要：

  DOI：

  10.1021/ja00791a074

文献信息

• A unified, RCM anchored approach to spiro[4.5]decane-based sesquiterpenoids: Collective synthesis of (±)-α & β-vetispirenes, (±)-β-vetivone, (±)-agarospirol and (±)-hinesol
  作者：Sudhakar Athe、Subhash Ghosh、Goverdhan Mehta

  DOI：10.1016/j.tetlet.2019.05.011

  日期：2019.6

  Collective syntheses of five spiro[4.5]decane framework bearing sesquiterpenoids, namely, α & β-vetispirenes, β-vetivone, agarospirol and hinesol as well as formal synthesis of axenol and gleenol from a readily available precursor cyclohexanone-β-ketoester via the intermediacy of a versatile intermediate (2,10-dimethylspiro[4.5]dec-1-en-6-one) have been accomplished in a concise manner.

  五种带有倍半萜类的螺[4.5]癸烷骨架的集体合成，即α和β-vetispirenes，β-vetivone，琼脂螺菌素和hinesol，以及通过中间剂从易得的前体环己酮-β-酮酸酯中正式合成阿森醇和格列醇通用的中间体（2,10-二甲基螺[4.5] dec-1-en-6-one）的合成已经很简洁。
• Structure/Odor Relationships of (&sminus 0;)- and (&splus 0;)-β-Vetivone, and Their Demethyl Derivatives
  作者：Helmut Spreitzer、Iris Piringer、Wolfgang Holzer、Michael Widhalm

  DOI：10.1002/(sici)1522-2675(19981216)81:12<2292::aid-hlca2292>3.0.co;2-k

  日期：1998.12.16

  (-)-beta-Vetivone ((-)3a), one of the main constituents of vetiver oil, was submitted to a structure/odor relationship study. The influence of the Me groups at the cyclohexenone ring and of the configuration on the odor was examined. Detailed H-1- and C-13-NMR-spectroscopic data were collected, and the absolute configurations were determined by CD methods.

  (-)-β-愈创木烯 [(-)-3a]，作为 vetiver 油的主要成分之一，进行了结构/气味关系研究。研究了环己烯酮环上的 Me 组团以及构型对气味的影响。收集了详细的 H-1- 和 C-13-NMR 波谱数据，并通过 CD 方法确定了绝对构型。
• A Synthesis of (±)-β-Vetivone and Its Related Spirovetivanes<i>via</i>the Base-catalyzed Spiroannelation of Phenolic Tosylates
  作者：Sigeru Torii、Kenji Uneyama、Kaoru Okamoto

  DOI：10.1246/bcsj.51.3590

  日期：1978.12

  (±)-β-Vetivone was synthesized by the base-catalyzed spiroannelation of 2-[2-(4-hydroxy-2-methylphenyl)-ethyl]-3-methyl-3-butenyl p-toluenesulfonate followed by methylation and subsequent isomerization of the side chain double bond. The reactivities of the related tosylates, 4-(4-hydroxy-2-methylphenyl)-2-isopropylbutyl p-toluenesulfonate, 3-hydroxy-2-[2-(4-hydroxy-2-methylphenylethyl]-3-methylbutyl

  (±)-β-Vetivone 是通过碱催化的 2-[2-(4-羟基-2-甲基苯基)-乙基]-3-甲基-3-丁烯基对甲苯磺酸酯的螺环化反应合成的，然后甲基化和随后的异构化侧链双键。相关甲苯磺酸盐、4-(4-羟基-2-甲基苯基)-2-异丙基丁基对甲苯磺酸盐、3-羟基-2-[2-(4-羟基-2-甲基苯基乙基]-3-甲基丁基对-甲苯磺酸盐的反应性甲苯磺酸盐和 2,3-环氧-2-[2-(4-羟基-2-甲基苯基)乙基]-3-甲基丁基对甲苯磺酸盐已经进行了讨论。
• A one-flask multicomponent annulation reaction as the key step in a total synthesis of spirobicyclic (±)-β-vetivone
  作者：Gary H. Posner、Ellen M. Shulman-Roskes

  DOI：10.1016/s0040-4020(01)81566-0

  日期：1992.6

  One-flask, 3-component Michael-Michael-Dieckmann cyclizations are applied to 2+2+2 construction of spirobicyclic cyclohexanone β-keto esters 7 and 11 as pivotal intermediates for synthesis of naturally-occurring spiro[4.5]decane β-vetivone (1). Some unexpected difficulties were encountered and are discussed. A novel BF3-promoted unidirectional dehydration of tertiary alcohol silyl ether 15 exclusively

  将一烧瓶，三成分的Michael-Michael-Dieckmann环化反应应用于螺双环环己酮β-酮酯7和11的2 + 2 + 2构造，作为合成天然存在的螺[4.5]癸烷β-vetivone的关键中间体（1）。遇到一些意外的困难并进行了讨论。报道了一种新颖的由BF 3促进的叔醇甲硅烷基醚15单向脱水成异亚丙基环戊烷16的方法。
• A new spiro-annelation procedure: intramolecular decarboxylative alkylation of β-keto-esters
  作者：Robert G. Eilerman、Brian J. Willis

  DOI：10.1039/c39810000030

  日期：——

  A new intramolecular decarboxylative alkylation route to spirocyclic ketones, and its application to the synthesis of (±)-β-vetivone and (±)-β-vetispirene are described.

  描述了一种新的分子内脱羧烷基化成螺环酮的路线，及其在合成（±）-β- vetivone和（±）-β- vetispirene中的应用。