(+)-δ-selinene | 28624-28-4

• 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-selinene
• 英文别名: δ-selinene；selina-4,6-dien；eudesma-4,6-diene；Eudesma-4,6-dien；2-Isopropyl-4aβ,8-dimethyl-3,4,4a,5,6,7,hexahydro-naphthalin；(+)-δ-Selinen；(+)-delta-Selinene；(8aR)-4,8a-dimethyl-6-propan-2-yl-2,3,7,8-tetrahydro-1H-naphthalene
• CAS: 28624-28-4
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: VEGYMPQCXPVQJY-OAHLLOKOSA-N

物化性质

• 沸点：
  105-110 °C(Press: 1 Torr)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 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：

  (+)-δ-selinene 在 palladium on activated charcoal 氢气 作用下， 以 正己烷 为溶剂， 反应 1.0h， 生成 4α(H)-eudesmane 、 (1S,4aR,7S,8aS)-7-Isopropyl-1,4a-dimethyl-decahydro-naphthalene
  参考文献：
  名称：

  (-)-7-epi-Isojunenol 和 (+)-7-epi-junenol，地衣 Tritomaria quinquedentata 的成分

  摘要：

  摘要 研究了地草 Tritomaria quinquedentata (Huds.) Buch 的倍半萜成分。除了许多已知化合物之外，还分离并鉴定了一种新的倍半萜醇，(-)-7-epi-isojunenol。(+)-7-epi-Junenol，另一种倍半萜醇，首次在自然界中被发现。

  DOI：

  10.1016/s0031-9422(99)00383-0
• 作为产物：
  描述：

  r-eudesmol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 0.08h， 以5.2 mg的产率得到(+)-δ-selinene
  参考文献：
  名称：

  A revision of the positive sign of the optical rotation and its maximum value of α-eudesmol

  摘要：

  The ether extract of the liverwort Porella perrottetiana afforded (-)-alpha-eudesmol, which showed an opposite sign of the optical rotation to that found in higher plants. Present work on the absolute configuration and an optical purity of (-)-alpha-eudesmol strongly suggested that the positive values (e.g. + 28.5 degrees) described in many previous papers should be revised. Since the absolute configuration of (-)-alpha-eudesmol was identical to that of (+)-beta-eudesmol found in the higher plants, it was apparent that the expression of the positive sign might be revised to (-)-alpha-eudesmol. The optical purity, reconfirmation of the absolute configuration and synthesis of (-)-alpha-eudesmol will be discussed. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(99)00299-x

文献信息

• Terpenoids—xli
  作者：M.L. Maheshwari、T.C. Jain、R.B. Bates、S.C. Bhattacharyya

  DOI：10.1016/s0040-4020(01)99363-9

  日期：1963.1

  sesquiterpenic furanoids of the selinane group have been isolated from agarwood oil, obtained from the fungus infected plant Aquillaria agallocha Roxb. and their structures and absolute configurations determined (XXII, XX, XXXI) by degradative studies and physical measurements.

  已从沉香木油中分离出三个新的亚硒醚类倍半萜类呋喃酮，该沉香油是从真菌感染的植物Aquillaria agallocha Roxb获得的。并通过退化研究和物理测量确定其结构和绝对构型（XXII，XX，XXXI）。
• Terpenoids—XLIII
  作者：B.S. Tyagi、B.B. Ghatge、S.C. Bhattacharyya

  DOI：10.1016/s0040-4020(01)98579-5

  日期：1963.1

  N-lithio-ethylenediamine as an isomerizing and dehydrogenating reagent has been further extended. It is useful for partial aromatization of cadinenic terpenes and for conversion of selenenic compounds to heteroannular diene, optical rotation of which throws light on the absolute configuration of the parent compound. It is also useful for smooth isomerization of fatty acid.

  N-硫代-乙二胺作为异构化和脱氢试剂的应用已得到进一步扩展。它对碱金属萜烯的部分芳构化以及硒代化合物向杂环状二烯的转化是有用的，后者的旋光性说明了母体化合物的绝对构型。对于脂肪酸的平滑异构化也是有用的。
• Sesquiterpene constituents from the essential oil of the liverwort Plagiochila asplenioides
  作者：Adewale Martins Adio、Wilfried A. König

  DOI：10.1016/j.phytochem.2005.01.015

  日期：2005.3

  The essential oil of the liverwort Plagiochila asplenioides from two different locations in Northern Germany were investigated by chromatographic and spectroscopic methods. Seven compounds were isolated by preparative gas chromatography (GC) and their structures investigated by mass spectrometry (MS), NMR techniques and chemical correlations in combination with enantioselective GC. In addition to known

  通过色谱法和光谱法研究了来自德国北部两个不同地点的地衣 Plagiochila asplenioides 的精油。通过制备型气相色谱 (GC) 分离出七种化合物，并通过质谱 (MS)、核磁共振技术和化学相关性结合对映选择性 GC 研究了它们的结构。除了已知成分，aromadendra-1(10),3-diene，两种芳香倍半萜烃，bisabola-1,3,5,7(14)-tetraene 和 bisabola-1,3,5,7-tetraene，三种除 ent-4-epi-maaliol 外，倍半萜醚、muurolan-4,7-peroxide、plagiochilines W 和 X 还首次被鉴定为天然化合物。
• Biogenetically patterned transformation of eudesmanolide to eremophilanolide. I. Angular methyl migration of 5.ALPHA.,6.ALPHA.-epoxy-dihydroalantolactone.
  作者：ISAO KITAGAWA、YASUSHI YAMAZOE、HIROTAKA SHIBUYA、REIJI TAKEDA、HIDEKAZU TAKENO、ITIRO YOSHIOKA

  DOI：10.1248/cpb.22.2662

  日期：——

  As a continuation of our study on the biogenetically patterned transformation leading to the natural terpenoids, conversion of an eudesmanolide directing to the related eremophilanolide was investigated and the object was accomplished. After several attempts, treatment of 5α, 6α-epoxy-dihydroalantolactone (15) with HCOOH-acetone (1 : 2) at reflux was found to afford eight products (A-H). Among them, two major products (products A and B) and one minor product (product D), which were obtained in a combined yield of 46%, were elucidated to be the desired eremophilanolides (17, 18, and 23) on the basis of the physicochemical evidence and the chemical conversion of 23 to tetrahydroligularenolide (34). The structure of the product C was assigned 20 on the basis of its physical properties and the chemical derivation. Afterwards, a better reaction condition transforming 15 to give 17 and 18 in a combined 68% yield was found.

  作为我们对天然萜类化合物生物基因型转化研究的延续，我们研究了从桉叶内酯向相关的埃瑞莫菲兰内酯的转化，并实现了这一目标。经过多次尝试，发现 5α，6α-环氧二氢金刚烷内酯（15）与 HCOOH-丙酮（1:2）在回流条件下处理可得到八种产物（A-H）。其中，两个主要产物（产物 A 和 B）和一个次要产物（产物 D）的总收率为 46%，根据理化证据和 23 转化为四氢愈创木酚内酯（34）的化学反应，这些产物被确定为所需的愈创木酚内酯（17、18 和 23）。根据产物 C 的物理性质和化学推导，确定了其结构为 20。之后，又找到了一种更好的反应条件，将 15 转化为 17 和 18，总产率为 68%。
• Sesquiterpenes of the liverwort Scapania undulata
  作者：Adewale Martins Adio、Claudia Paul、Petra Kloth、Wilfried A König

  DOI：10.1016/j.phytochem.2003.10.018

  日期：2004.1

  The essential oil of the liverwort Scapania undulata, collected in the Harz mountains, Northern Germany, was analysed by gas chromatography (GC), GC-mass spectrometry (MS) and several new components were isolated and investigated by various NMR techniques. As new natural compounds the sesquiterpene hydrocarbons (+)-helminthogermacrene (1) [the 4Z-isomer of germacrene A (9)], (-)-cis-beta-elemene (2)

  通过气相色谱 (GC)、GC-质谱 (MS) 分析收集在德国北部哈尔茨山脉的地衣 Scapania undulata 精油，并通过各种 NMR 技术分离和研究了几种新成分。作为新的天然化合物，倍半萜烃 (+)-helminthogermacrene (1) [germacrene A (9) 的 4Z-异构体]，(-)-cis-beta-elemene (2) 作为 1 的 Cope 重排产物，（ +)-beta-isolongibornene (3) 和 (-)-perfora-1,7-diene (4) 可以被识别。图 1 与锗烯 A (9) 具有相同的质谱和相同的非极性固定相上的 GC 保留时间，但比后者稳定得多。1 的 Cope 重排在 350 摄氏度下缓慢进行，并且 (-)-cis-beta-elemene (2) 与少量其他非对映异构体一起形成。