(+/-)-Essigsaeure-<(6E)-8-hydroxy-2,6-dimethyl-1,6-octadien-3-yl>ester | 130697-19-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (+/-)-Essigsaeure-<(6E)-8-hydroxy-2,6-dimethyl-1,6-octadien-3-yl>ester
• 英文别名: [(6E)-8-hydroxy-2,6-dimethylocta-1,6-dien-3-yl] acetate
• CAS: 130697-19-7
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: ISRUBRIBXHBLEM-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-Essigsaeure-<(6E)-8-hydroxy-2,6-dimethyl-1,6-octadien-3-yl>ester 在 lithium aluminium tetrahydride 、 三氟化硼乙醚 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 1.0h， 生成 2β,4-dimethyl-4-vinylcyclohexane-1α,2α-diol
  参考文献：
  名称：

  Electrophilic cyclization of ?-series monoterpene ?-derivatives

  摘要：

  New information is discussed concerning the protic and Lewis acid-initiated electrophilic cyclization reaction of alpha-monoterpenols and their acetates; the distinguishing feature of these reactions is their termination by isopropenyl residues in these molecules. The reactions have been found to be general in nature, given additional functionalization of the terminator by chloro-, sulfonyl, sulfonylmethyl, or ester substituents. Cyclization of these linear substrates has also been shown to provide a convenient method for the synthesis of dimethylvinylcyclohexene derivatives and related cyclohexanediols, which are not readily available by other methods.

  DOI：

  10.1007/bf00962388
• 作为产物：
  描述：

  2,6-dimethyl-3-acetoxy-8-(2-tetrahydropyranyloxy)octa-1,6E-diene 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以96%的产率得到(+/-)-Essigsaeure-<(6E)-8-hydroxy-2,6-dimethyl-1,6-octadien-3-yl>ester
  参考文献：
  名称：

  Electrophilic cyclization of ?-series monoterpene ?-derivatives

  摘要：

  New information is discussed concerning the protic and Lewis acid-initiated electrophilic cyclization reaction of alpha-monoterpenols and their acetates; the distinguishing feature of these reactions is their termination by isopropenyl residues in these molecules. The reactions have been found to be general in nature, given additional functionalization of the terminator by chloro-, sulfonyl, sulfonylmethyl, or ester substituents. Cyclization of these linear substrates has also been shown to provide a convenient method for the synthesis of dimethylvinylcyclohexene derivatives and related cyclohexanediols, which are not readily available by other methods.

  DOI：

  10.1007/bf00962388

文献信息

• Synthesen der enantiomeren Aleuriaxanthine. Nachweis eines vorherrschenden (Z)-Aleuriaxanthins inAleuria
  作者：Walter Eschenmoser、Peter Uebelhart、Conrad Hans Eugster

  DOI：10.1002/hlca.19830660110

  日期：1983.2.2

  Syntheses of the Enantiomeric Aleuriaxanthins. Detection of a Predominant (Z)-Aleuriaxanthin in Aleuria

  对映体鸢尾黄质的合成。Aleuria中主要的（Z）-无油黄质的检测
• Palladium catalyzed oxidation of biorenewable β-citronellol and geraniol for the synthesis of polyfunctionalized fragrances
  作者：Aldino N. Venancio、Luciano Menini、Daiane N. Maronde、Elena V. Gusevskaya、Luciana A. Parreira

  DOI：10.1016/j.mcat.2021.111449

  日期：2021.3

  plants. Allylic oxidation of trisubstituted sterically highly encumbered carbon-carbon double bonds in their molecules with dioxygen can be efficiently catalyzed by the palladium acetate/p-benzoquinone combination under 5−10 atm of dioxygen pressure without the need for conventionally used metal co-catalysts. Both substrates gave allyl acetates in ca. 90% combined yield. The oxidation of geraniol proceeded

  β-香茅醇和香叶醇是在各种植物的精油中发现的可生物再生的化合物。乙酸钯/对苯醌的组合可在5-10 atm的氧气压力下，有效地催化三取代的空间取代分子中高度取代的碳-碳双键在分子中的烯丙基氧化反应，而无需常规使用的金属助催化剂。两种底物在约70℃下均得到乙酸烯丙酯。合并产率为90％。香叶醇的氧化具有出色的位点选择性，仅涉及其两个C之一C键。香叶醇以可比的产率产生直链和支链乙酸烯丙酯，而β-香茅醇的反应对相应的支链产物显示出高区域选择性。由β-香茅醇和香叶醇生产的多官能氧化的萜烯作为香料组合物的成分具有潜在的重要性。
• MOISEENKOV, A. M.;DRAGAN, V. A.;VESELOVSKIJ, V. V.;CHESKIS, B. A.;SHPIRO,+, IZV. AN CCCP. CEP. XIM.,(1990) N, S. 1361-1367
  作者：MOISEENKOV, A. M.、DRAGAN, V. A.、VESELOVSKIJ, V. V.、CHESKIS, B. A.、SHPIRO,+

  DOI：——

  日期：——