(+)-daucene | 38601-99-9

• 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: (+)-daucene
• 英文别名: (8aR)-6,8a-dimethyl-3-propan-2-yl-2,4,5,8-tetrahydro-1H-azulene
• CAS: 38601-99-9
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: MGMBZNCFUFRSSP-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  (+)-daucene 在 palladium on activated charcoal 氢气 作用下， 以 正己烷 为溶剂， 反应 1.0h， 生成 Azulene, decahydro-3a,6-dimethyl-1-(1-methylethyl)-
  参考文献：
  名称：

  Volatile constituents in mosses (Musci)

  摘要：

  The essential oils of mosses of the genera Mnium, Plagiomnium, Homalia, Plagiothecium and Taxiphyllum (Musci) have been investigated by gas chromatography and mass spectrometry. The new sesquiterpenes (+)-10-epi-muurola-4,11-diene and 10,11-dihydro-alpha -cuparenone were isolated by preparative e gas chromatography and identified as major constituents of the hydrodistillation products of Mnium hornum (Hedw.) using NMR and mass spectrometry. In addition, (+)-dauca-8,11-diene and two new butenolides. 3.4,5-trimethyl-5-pentyl-5H-furan-2-one and 3.4-dimethyl-5-pentyl-5H-furan-2-one were identilied as constituents in Plagiomnium undulatum (Hedw.) T. Kop. Although the amounts of volatiles present in the investigated mosses are generally smaller than in liverworts, the spectrum of terpenoid compounds is similar. The investigated mosses also generate aliphatic compounds of greater abundance and structural variety. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(01)00069-3
• 作为产物：
  描述：

  (1S)-1-methyl-8-isopropylbicyclo<5.3.0>deca-3,7-dien-2-one 在 rhodium(III) chloride 、 copper (I) iodide 、 lithium 、 三乙胺 、 叔丁醇 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 9.17h， 生成 (+)-daucene
  参考文献：
  名称：

  一种新的且易形成的全氢氮杂形成：胡萝卜素（+）-丁二烯的全合成

  摘要：

  2,5-双（三甲基甲硅烷氧基）三环| 4.4.0.0 2,5 | decan-7-ones通过跨环反应生成过氢azulenes，该跨环反应涉及中间体环癸二烯酮中甲硅烷基的氧迁移至氧。2-环己烯酮向全氢氮杂烯的这种三步转化通过胡萝卜素（+）-丁二烯（）的合成来说明。

  DOI：

  10.1016/s0040-4020(01)87740-1

文献信息

• A Unified Approach to the Daucane and Sphenolobane Bicyclo[5.3.0]decane Core: Enantioselective Total Syntheses of Daucene, Daucenal, Epoxydaucenal B, and 14-<i>para</i>-Anisoyloxydauc-4,8-diene
  作者：Nathan B. Bennett、Brian M. Stoltz

  DOI：10.1002/chem.201302353

  日期：2013.12.23

  enone intermediate enables the enantioselective total syntheses of daucene, daucenal, epoxydaucenal B, and 14‐para‐anisoyloxydauc‐4,8‐diene. Central aspects include a catalytic asymmetric alkylation followed by a ring contraction and ring‐closing metathesis to generate the five‐ and seven‐membered rings, respectively.

  通过关键的烯酮中间体获得在胡萝卜烷和酚烷萜类化合物中发现的双环[5.3.0]癸烷核心，可以对映体选择性地全合成胡萝卜烯、胡萝卜烯醛、环氧胡萝卜醛B和14-对茴香酰氧基胡萝卜烯-4,8-​​二烯。核心方面包括催化不对称烷基化，然后进行环收缩和闭环复分解，分别生成五元环和七元环。
• 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。
• Chemical Transformations of Carotol Isolated from Carrot Seed Oil
  作者：D. Kataria、K.K. Chahal、A. Kumar

  DOI：10.14233/ajchem.2016.19830

  日期：——

  Previous phytochemical studies on the essential oil of carrot seed revealed the presence of carotol as the major compound. In the present study the essential oil of carrot seed extracted by Dean and Stark apparatus was analyzed by gas chromatography-mass spectrometry. A total of 51 compounds were identified. Carotol, a sesquiterpenoid was found to be the major compound whereas daucol, daucene, b-cubenene and b-farnesene were the minor compounds present. Carotol (52 %) was isolated by column chromatography. Chemical reactions of carotol with N-bromosuccinimide, selenium dioxide/t-butyl hydrogen peroxide, phenol/sulfuric acid and p-toluene sulfonic acid were carried out and structures of these compounds were elucidated on the basis of FTIR, 1H NMR and 13C NMR spectroscopy.

  之前对胡萝卜籽精油的植物化学研究表明，胡萝卜醇是主要化合物。在本研究中，通过气相色谱-质谱联用仪对用迪恩和斯塔克装置提取的胡萝卜籽精油进行了分析。共鉴定出51种化合物。其中，主要化合物为倍半萜类化合物胡萝卜醇，次要化合物为daucol、daucene、β-cubenene和β-farnesene。通过柱色谱法分离出胡萝卜醇（52%）。对胡萝卜醇与N-溴代琥珀酰亚胺、二氧化硒/叔丁基过氧化氢、苯酚/硫酸和对甲苯磺酸的反应进行了研究，并根据FTIR、1H NMR和13C NMR光谱阐明了这些化合物的结构。
• Sesquiterpene constituents of the liverwort Bazzania trilobata
  作者：Ute Warmers、Wilfried A König

  DOI：10.1016/s0031-9422(99)00123-5

  日期：1999.9

  Abstract The sesquiterpene constituents of the liverwort Bazzania trilobata (L.) Gray were investigated. In addition to many known compounds two new sesquiterpene hydrocarbons, (−)- cis -cadina-1(6),4-diene and (+)- trans -dauca-4(11),8-diene, could be isolated and identified. The structure elucidation was carried out by NMR spectroscopic techniques and chemical conversions.

  摘要 研究了地草 Bazzania trilobata (L.) Gray 的倍半萜成分。除了许多已知化合物外，还可以分离和鉴定两种新的倍半萜烃，(-)- cis -cadina-1(6),4-diene 和 (+)- trans -dauca-4(11),8-diene . 通过核磁共振光谱技术和化学转化进行结构解析。
• Revisiting the Male-Produced Aggregation Pheromone of the Lesser Mealworm,<i>Alphitobius diaperinus</i>(Coleoptera, Tenebrionidae): Identification of a Six-Component Pheromone from a Brazilian Population
  作者：Marla J. Hassemer、Josué Sant’Ana、Miguel Borges、David Withall、John A. Pickett、Márcio W. M. de Oliveira、Raul A. Laumann、Michael A. Birkett、Maria C. Blassioli-Moraes

  DOI：10.1021/acs.jafc.6b02235

  日期：2016.9.14

  The lesser mealworm, Alphitobius diaperinus Panzer 1797 (Coleoptera: Tenebrionidae), is a cosmopolitan insect pest affecting poultry production. Due to its cryptic behavior, insecticide control is usually not efficient. Thus, sustainable and effective methods would have an enormous and positive impact in poultry production. The aim of this study was to confirm the identity of the male-produced aggregation pheromone for a Brazilian population of A. diaperinus and to evaluate its biological activity in behavioral assays. Six male-specific compounds were identified: (R)-limonene (1), (E)-ocimene (2), 2-nonanone (3), (S)-linalool (4), (R)-daucene (5), all described before in an American population, and a sixth component, (E,E)-alpha-farnesene (6), which is apparently exclusive to a Brazilian population. Y-Tube bioassays confirmed the presence of a male-produced aggregation pheromone and showed that all components need to be present in a similar ratio and concentration as emitted by male A. diaperinus to produce a positive chemotactic response.