δ-elemene | 80796-88-9

• 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: δ-elemene
• 英文别名: δ-Elemen；(3S,4S)-4-ethenyl-4-methyl-1-propan-2-yl-3-prop-1-en-2-ylcyclohexene
• CAS: 80796-88-9
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: MXDMETWAEGIFOE-LSDHHAIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  δ-elemene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 生成 Tetrahydro-δ-elemen
  参考文献：
  名称：

  Gough,J.H.; Sutherland,M.D., Australian Journal of Chemistry, 1964, vol. 17, p. 1270 - 1281

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-nitro-benzoyloxy)-2-((1R)-4c-methyl-4t-vinyl-3c-isopropenyl-cyclohexyl-(r))-propane 生成 δ-elemene
  参考文献：
  名称：

  分子和二氢geijeren-Reihe中的热解和水合大肠菌

  摘要：

  Abstract The pyrolysis of elemol (1) in the presence of benzoic or p‐nitrobenzoic acid, and of elemyl‐p‐nitrobenzoate (3) was studied. From the many products formed, the compounds 6, 7, 8, 10, 11, 14, 15 and 18 were isolated and identified. On the basis of systematic experiments in the elemol (1) and dihydrogeijerene (26) series the sequence of the formation of these products could be determined. Several factors influencing the compositions of the pyrolysis mixtures are discussed. The products of pyrolysis of both series [elemol (1) and dihydrogeijerene (26), respectively] were catalytically hydrogenated, yielding the saturated hydrocarbons 34, 35–37, and 38–40, respectively. The synthesis of racemic dihydrogeijerene (26) was achieved starting from germacrone (41).

  DOI：

  10.1002/hlca.19710540117

文献信息

• The role of germacrene D as a precursor in sesquiterpene biosynthesis: investigations of acid catalyzed, photochemically and thermally induced rearrangements
  作者：Nils Bülow、Wilfried A König

  DOI：10.1016/s0031-9422(00)00266-1

  日期：2000.9

  Germacrene D is considered as a precursor of many sesquiterpene hydrocarbons. We have investigated the acid catalyzed as well as the photochemically and thermally induced rearrangement processes of germacrene D isolated from several Solidago species, which contain both enantiomers of germacrene D. Enantiomeric mixtures of sesquiterpenes of the cadinane, eudesmane (selinane), oppositane, axane, isodaucane

  Germacrene D 被认为是许多倍半萜烃的前体。我们研究了从几种一枝黄花物种中分离出的锗烯 D 的酸催化以及光化学和热诱导的重排过程，其中含有锗烯 D 的两种对映异构体。 cadinane、eudesmane (selinane)、opp​​ositane、axane、异十二烷和波旁烷组以及异热菌烯 D 被确定为主要产品，并可作为参考化合物用于植物成分的结构研究和立体化学分配。重排产物之一的 Delta-amorphene 首次被确定为天然产物。γ-阿吗啡的绝对构型通过与锗烯 D 的绝对构型的相关性进行了修正。
• Reaction of Elemol with Acetic Acid/Perchloric Acid: Characterization of a Novel Oxide and (+)-β-Cyperone
  作者：Solimabi Wahidulla、Mangala Babu Govenkar、Sashikumar Keshav Paknikar

  DOI：10.1002/hlca.200690050

  日期：2006.3

  The minor unidentified compounds of the acetic acid/perchloric acid dehydration of elemol (1) were fully characterized. The structure and relative configuration of the less polar fragrant compound 2, named elemoxide, was deduced by 1D- and 2D-NMR data including C,C-connectivity, NOE, and NOESY experiments. The absolute configuration was established as (3S,3aR,7aR)-1,3,3a,4,7,7a-hexahydro-6-isopropyl-1

  充分表征了elemol（1）的乙酸/高氯酸脱水的次要化合物。通过1D-和2D-NMR数据（包括C，C连接性，NOE和NOESY实验）推导了极性较小的芳香化合物2（称为榄香精）的结构和相对构型。在此基础上将绝对构型确定为（3 S，3a R，7a R）-1,3,3a，4,7,7a-六氢-6-异丙基-1,1,3,3a-四甲基异苯并呋喃（2）由elemol（1）制备。（+）- β-香芹酮（3），一种已知的倍半萜烯，也被确定为该反应的次要产物。提出了合理的机理解释，用于形成榄香氧化物（2）和（+）- β- cyperone（3）。
• [EN] NOVEL SESQUITERPENE OXIDES AS PERFUMING AND FLAVOURING AGENTS<br/>[FR] NOUVEAUX OXYDES DE SESQUITERPENE COMME AGENTS PARFUMANTS ET AROMATISANTS
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2004085417A1

  公开（公告）日：2004-10-07

  The present invention describes the process for the preparation of novel sesquiterpene oxide 3S, 3aR, 7aR, -6 isopropyl- 1,1,3,3a - tetramethyl 1,3,3a,4,7,7a- hexahydro-isobenzofuran, of formula (I) by the reaction of elemol with per acid at a temperature range of 20 to 30°C. The invention also deals with the use of compound of formula (1) as a perfuming and flavouring agent.

  本发明描述了制备新型倍半萜氧化物3S、3aR、7aR、-6异丙基-1,1,3,3a-四甲基1,3,3a,4,7,7a-六氢异苯并呋喃（式（I））的过程，该过程是通过将艾莫尔与过氧酸在20至30°C的温度范围内反应而得到的。本发明还涉及将式（1）化合物用作香料和味道剂的用途。
• The sesquiterpene constituents of the liverwort Preissia quadrata
  作者：Wilfried A. König、Nils Bülow、Christiane Fricke、Stephanie Melching、Angela Rieck、Hermann Muhle

  DOI：10.1016/0031-9422(96)00354-8

  日期：1996.10

  Abstract The labile sesquiterpene hydrocarbon germacrene C is the main constituent of a chemotype of the liverworth Preissia quadrata collected in Southern Germany. Its temperature dependent rearrangement to racemic δ-elemene is observed by capillary gas chromatography using cyclodextrins as chiral stationary phases. In addition, the rarely found ent -sesquiterpenes (+)-germacrene D, (+)- trans - β

  摘要 不稳定的倍半萜烃锗烯 C 是在德国南部采集的liverworth Preissia quadrata 化学型的主要成分。通过使用环糊精作为手性固定相的毛细管气相色谱观察到其温度依赖性重排为外消旋 δ-榄香烯。此外，罕见的ent-倍半萜烯(+)-germacrene D、(+)-反式-β-石竹烯、(+)-β-石竹烯氧化物、(+)-cubebol和外消旋alismol [1β,5α-guaia-6 ,10(15)-dien-4-ol] 被确定为使用光谱方法和对映选择性气相色谱的主要成分。次要成分是 (+)-α-copaene、(+)-δ-selinene、(-)-δ-cadinene、germacrene B 和 (-)-cascarilladiene (eudesma-5,7-diene)。
• Vig, O. P., Journal of the Indian Chemical Society, 1982, vol. 59, # 5, p. 609 - 616
  作者：Vig, O. P.

  DOI：——

  日期：——