3,10-epoxy myrcene | 153079-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 3,10-epoxy myrcene
• 英文别名: myrcene-3,10-epoxide；2-(4-methylpent-3-en-1-yl)-2-vinyloxirane；2-Ethenyl-2-(4-methylpent-3-enyl)oxirane
• CAS: 153079-55-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: LLKLWIXSUNDIKM-UHFFFAOYSA-N

物化性质

• 沸点：
  198.8±9.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,10-epoxy myrcene 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以78%的产率得到芳樟醇
  参考文献：
  名称：

  Epoxides from Myrcene: New Versatile Tools for the Synthesis of Functionalized Acyclic Terpenoids

  摘要：

  Mono-epoxides prepared from myrcene, were used as synthetic intermediates to obtain citral, linalool, geranylacetone and pseudo-ionone.

  DOI：

  10.1080/00397919908086005
• 作为产物：
  描述：

  月桂烯 在 吡啶 、 potassium permanganate 、 苄基三丁基氯化铵 、 potassium hydroxide 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 3,10-epoxy myrcene
  参考文献：
  名称：

  Redox-Triggered C–C Coupling of Alcohols and Vinyl Epoxides: Diastereo- and Enantioselective Formation of All-Carbon Quaternary Centers via tert-(Hydroxy)-Prenylation

  摘要：

  Iridium catalyzed primary alcohol oxidation triggers reductive C-O bond cleavage of isoprene oxide to form aldehyde-allyliridium pairs that combine to form products of tert-(hydroxy)-prenylation, a motif found in >2000 terpenoid natural products. Curtin-Hammett effects are exploited to enforce high levels of anti-diastereo- and enantioselectivity in the formation of an all-carbon quaternary center. The present redox-triggered carbonyl additions occur in the absence of stoichiometric byproducts, premetalated reagents, and discrete alcohol-to-aldehyde redox manipulations.

  DOI：

  10.1021/ja504625m

文献信息

• Intramolecular Vinyl Quinone Diels–Alder Reactions: Asymmetric Entry to the Cordiachrome Core and Synthesis of (−)-Isoglaziovianol
  作者：Florian Löbermann、Lara Weisheit、Dirk Trauner

  DOI：10.1021/ol401787n

  日期：2013.9.6

  A short and asymmetric entry to the core structure of the cordiachromes has been developed, allowing access to (−)-isoglaziovianol in seven steps. Our synthesis includes a Trost asymmetric allylic alkylation and a reaction cascade triggered by a vinyl quinone Diels–Alder reaction and followed by intramolecular nucleophilic interception.

  已经开发出一种简短且不对称的堇青色核心结构入口，可通过七个步骤进入（-）-异glaziovianol。我们的合成包括Trost不对称烯丙基烷基化反应和由乙烯基醌Diels-Alder反应触发的反应级联，然后进行分子内亲核拦截。
• Epoxides from Myrcene: Selective Obtention
  作者：Valéry Fauchet、Bernadette Arreguy-San Miguel、Martine Taran、Bernard Delmond

  DOI：10.1080/00397919308012583

  日期：1993.9

  1,2-and 3,10-epoxy myrcene are selectively obtained from dihydroxy derivatives prepared by an oxidation reaction of myrcene with potassium permanganate.
• Epoxides from Myrcene: New Versatile Tools for the Synthesis of Functionalized Acyclic Terpenoids
  作者：V. Fauchet、B. Arreguy-San Miguel、M. Taran、B. Delmondo

  DOI：10.1080/00397919908086005

  日期：1999.11

  Mono-epoxides prepared from myrcene, were used as synthetic intermediates to obtain citral, linalool, geranylacetone and pseudo-ionone.
• Redox-Triggered C–C Coupling of Alcohols and Vinyl Epoxides: Diastereo- and Enantioselective Formation of All-Carbon Quaternary Centers <i>via tert</i>-(Hydroxy)-Prenylation
  作者：Jiajie Feng、Victoria J. Garza、Michael J. Krische

  DOI：10.1021/ja504625m

  日期：2014.6.25

  Iridium catalyzed primary alcohol oxidation triggers reductive C-O bond cleavage of isoprene oxide to form aldehyde-allyliridium pairs that combine to form products of tert-(hydroxy)-prenylation, a motif found in >2000 terpenoid natural products. Curtin-Hammett effects are exploited to enforce high levels of anti-diastereo- and enantioselectivity in the formation of an all-carbon quaternary center. The present redox-triggered carbonyl additions occur in the absence of stoichiometric byproducts, premetalated reagents, and discrete alcohol-to-aldehyde redox manipulations.