(+/-)-α-Vetispiren | 51196-11-3

• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: (+/-)-α-Vetispiren
• 英文别名: (+/-)-α-Vetispirene；(5R,6S)-6,10-dimethyl-3-prop-1-en-2-ylspiro[4.5]deca-3,9-diene
• CAS: 51196-11-3
• 化学式: C₁₅H₂₂
• 分子量: 202.34
• InChiKey: KEVTZKPBXQTBSV-DZGCQCFKSA-N

物化性质

• 沸点：
  289.9±10.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-{1-[2,6-Dimethyl-cyclohex-2-en-(Z)-ylidenemethyl]-cyclopropyl}-propan-2-ol 在 正丁基锂 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 (+/-)-α-Vetispiren
  参考文献：
  名称：

  Silicon in organic synthesis. 16. A short synthesis of (+±)-α-vetispirene

  摘要：

  DOI：

  10.1016/s0040-4039(00)87576-0

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。
• Connective Synthesis of Spirovetivanes: Total Synthesis of (±)-Agarospirol, (±)-Hinesol and (±)-α-Vetispirene
  作者：Nuno Maulide、Jean-Christophe Vanherck、István E. Markó

  DOI：10.1002/ejoc.200400236

  日期：2004.10

  A concise, connective synthesis of naturally occurring spirovetivanes 1 and 3, in racemic form, is presented. This novel approach involves the efficient assembly of the advanced intermediate 12 through a unique spiroannulation protocol.

  介绍了外消旋形式的天然 spirovetivanes 1 和 3 的简洁、连接合成。这种新颖的方法涉及通过独特的螺环化方案高效组装高级中间体 12。
• Highly regioselective α-alkylation of γ-acetoxy-α, β-enoates by reduction–alkylation with lithium dibutylcuprate–alkyl halides: application to the synthesis of spirovetivanes
  作者：Toshiro Ibuka、Takeshi Aoyagi、Fumio Yoneda

  DOI：10.1039/c39850001452

  日期：——

  Reaction of γ-acetoxy-α, β-enoates with lithium dibutylcuprate followed by alkyl halides results in the predominant or exclusive formation of α-alkyl-β, γ-enoates in high yields under mild conditions; a synthetic route to (±)-α-vetispirene is also presented.

  γ-乙酰氧基-α - β-烯酸酯与二丁基铜酸锂反应，然后与烷基卤反应，导致在温和条件下以高收率主要或独家形成α-烷基-β-γ-烯酸酯。还提出了合成（±）-α- vetispirene的途径。
• Stereoselective total synthesis of (±)-α-vetispirene, (±)-hinesol, and (±)-β-vetivone based on a Claisen rearrangement
  作者：Atsuo Nakazaki、Tomohiro Era、Yuko Numada、Susumu Kobayashi

  DOI：10.1016/j.tet.2006.04.049

  日期：2006.6

  The stereoselective total syntheses of (±)-α-vetispirene, (±)-hinesol, and (±)-β-vetivone were accomplished based on a Claisen rearrangement in an alkenyl bicyclic dihydropyran system. The most striking feature of this approach is that the Claisen rearrangement of bicyclic dihydropyran proceeds stereoselectively to provide a multi-functionalized spiro[4.5]decane, which is an efficient precursor for

  基于在烯基双环二氢吡喃体系中的克莱森重排，完成了（±）-α-香螺碳烯，（±）-海索酚和（±）-β-香根酮的立体选择性全部合成。该方法最显着的特征是双环二氢吡喃的克莱森重排选择性进行，以提供多功能的螺[4.5]癸烷，这是合成香根草倍半萜的有效前体。
• Silicon in organic synthesis. 25. Thermolysis and desiliconation-alkylation of [1-(trimethylsilyl)cyclopropyl]ethylenes as a route to spirocyclic sesquiterpenes
  作者：Leo A. Paquette、Tu Hsin Yan、Gregory J. Wells

  DOI：10.1021/jo00193a031

  日期：1984.9