(E)‐α‐bisabolene | 25532-79-0

• 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: (E)‐α‐bisabolene
• 英文别名: (E)‐γ‐bisabolene；trans-α-bisabolene；(E)-α-bisabolene；bisabola-2,7E,10-triene；cis-α-bisabolene；trans-alpha-bisabolene；(E)-alpha-bisabolene；1-methyl-4-[(2E)-6-methylhepta-2,5-dien-2-yl]cyclohexene
• CAS: 25532-79-0
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: YHBUQBJHSRGZNF-VGOFMYFVSA-N

物化性质

• 沸点：
  276.9±25.0 °C(Predicted)
• 密度：
  0.859±0.06 g/cm3(Predicted)
• LogP：
  6.605 (est)
• 保留指数：
  1534;1534;1533;1527;1557;1530;1533;1533;1530;1547;1532;1537;1543

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 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

• 作为产物：
  描述：

  (2Z,6Z)-3,7,11-三甲基-2,6,10-十二碳三烯-1-醇 在 (2,4,6-tri-tert-butylphenoxy)-isobutylaluminium trifluormethanesulfonate 、 三溴化磷 、 sodium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 为溶剂， 反应 14.0h， 生成 (E)‐α‐bisabolene
  参考文献：
  名称：

  手性离去基团：柠檬烯和双sabolene的不对称合成

  摘要：

  描述了柠檬烯和双硼氢化萘的生物遗传型不对称合成。作为当前不对称合成的模型研究，对邻苯二酚，联苯酚和联萘酚单烯丙基醚1、4和5与有机铝试剂的环化反应以柠檬烯为主要产品。由于在相似的条件下1、4和5的反应已被证明比神经烷基苯基醚的反应快得多，因此速率加速归因于与邻羟基键合的铝试剂的新型金属-氨基酸辅助作用。影响烯丙基阳离子的产生。在修饰的铝试剂9处理后，这种对映异构效应可用于（R）-（+）-1,1'-联-2-萘酚单戊醚（8）的对映选择性环化，以生产具有高光学纯度（77％）的li烯。 ee）。

  DOI：

  10.1016/s0040-4020(01)90598-8

文献信息

• Modular terpene synthesis enabled by mild electrochemical couplings
  作者：Stephen J. Harwood、Maximilian D. Palkowitz、Cara N. Gannett、Paulo Perez、Zhen Yao、Lijie Sun、Héctor D. Abruña、Scott L. Anderson、Phil S. Baran

  DOI：10.1126/science.abn1395

  日期：2022.2.18

  biosynthesis is a case study of how the logic of a modular design can lead to diverse structures with unparalleled efficiency. This work leverages modern nickel-catalyzed electrochemical sp 2 –sp 3 decarboxylative coupling reactions, enabled by silver nanoparticle–modified electrodes, to intuitively assemble terpene natural products and complex polyenes by using simple modular building blocks. The step change

  萜烯的合成是一个广泛的研究领域，它深深地融入了化学史。萜烯生物合成是一个案例研究，说明模块化设计的逻辑如何以无与伦比的效率产生多样化的结构。这项工作利用现代镍催化电化学 sp2个–sp3个由银纳米粒子修饰的电极实现的脱羧偶联反应，通过使用简单的模块化构建块直观地组装萜烯天然产物和复杂的多烯。通过可扩展制备 13 种复杂萜烯，可以最大限度地减少保护基团操作、官能团相互转化和氧化还原波动，证明了这种方法在效率上的阶跃变化。通过各种光谱和分析技术深入研究了基本功能化电极的机械方面。
• Chiral leaving group. Biogenetic-type asymmetric synthesis of limonene and bisabolenes
  作者：Soichi Sakane、Junya Fujiwara、Keiji Maruoka、Hisashi Yamamoto

  DOI：10.1021/ja00357a033

  日期：1983.9

  On prepare les composes du titre a partir des ethers obtenus par reaction des bromures de neryle et de farnesyle avec le binaphtyle-1,1' diol-2,2' et le biphenylediol-2,2'

  在制备 les composes du titre a partir des ethers obtenus par reaction des bromures de neryle et de farnesyle avec le binaphtyle-1,1' diol-2,2' et le biphenylediol-2,2'
• Novel family of terpene synthases evolved from <i>trans</i> -isoprenyl diphosphate synthases in a flea beetle
  作者：Franziska Beran、Peter Rahfeld、Katrin Luck、Raimund Nagel、Heiko Vogel、Natalie Wielsch、Sandra Irmisch、Srinivasan Ramasamy、Jonathan Gershenzon、David G. Heckel、Tobias G. Köllner

  DOI：10.1073/pnas.1523468113

  日期：2016.3.15

  Whether insect sesquiterpenes are synthesized de novo, derived from plant precursors, or produced by symbionts is often unknown. We identified an evolutionarily novel terpene synthase gene family in the striped flea beetle, a notorious pest of Brassica crops in North America and Asia, and one of these genes was shown to be directly involved in the biosynthesis of the male-specific sesquiterpene aggregation pheromone. Phylogenetic and gene structure analyses indicate that an expansion of the trans -isoprenyl diphosphate synthase gene family in the ancestor of the subfamily Galerucinae enabled functional diversification toward this terpene synthase gene family. These insights into how flea beetles synthesize their aggregation pheromones may lead to new approaches for pest management.

  无论昆虫倍半萜是通过新合成、从植物前体中衍生或由共生菌产生，通常都是未知的。我们在斑纹跳蚤甲中鉴定出了一种进化上新颖的萜类合成酶基因家族，这是北美和亚洲油菜作物的臭名昭著害虫之一，其中一个基因被证明直接参与了雄性特异性倍半萜聚集信息素的生物合成。系统发育和基因结构分析表明，在长臂叶甲亚科祖先中，转 -异戊烯基二磷酸合酶基因家族的扩张使得功能多样化朝着这个萜类合成酶基因家族发展。对斑纹跳蚤如何合成其聚集信息素的这些见解可能会导致新的害虫管理方法。

• RNA-seq discovery, functional characterization, and comparison of sesquiterpene synthases from Solanum lycopersicum and Solanum habrochaites trichomes
  作者：Petra M. Bleeker、Eleni A. Spyropoulou、Paul J. Diergaarde、Hanne Volpin、Michiel T. J. De Both、Philipp Zerbe、Joerg Bohlmann、Vasiliki Falara、Yuki Matsuba、Eran Pichersky、Michel A. Haring、Robert C. Schuurink

  DOI：10.1007/s11103-011-9813-x

  日期：2011.11

  Solanum lycopersicum and Solanum habrochaites (f. typicum) accession PI127826 emit a variety of sesquiterpenes. To identify terpene synthases involved in the production of these volatile sesquiterpenes, we used massive parallel pyrosequencing (RNA-seq) to obtain the transcriptome of the stem trichomes from these plants. This approach resulted initially in the discovery of six sesquiterpene synthase cDNAs from S. lycopersicum and five from S. habrochaites. Searches of other databases and the S. lycopersicum genome resulted in the discovery of two additional sesquiterpene synthases expressed in trichomes. The sesquiterpene synthases from S. lycopersicum and S. habrochaites have high levels of protein identity. Several of them appeared to encode for non-functional proteins. Functional recombinant proteins produced germacrenes, β-caryophyllene/α-humulene, viridiflorene and valencene from (E,E)-farnesyl diphosphate. However, the activities of these enzymes do not completely explain the differences in sesquiterpene production between the two tomato plants. RT-qPCR confirmed high levels of expression of most of the S. lycopersicum sesquiterpene synthases in stem trichomes. In addition, one sesquiterpene synthase was induced by jasmonic acid, while another appeared to be slightly repressed by the treatment. Our data provide a foundation to study the evolution of terpene synthases in cultivated and wild tomato.

  番茄（Solanum lycopersicum）和哈勃罗切特番茄（Solanum habrochaites）（f. typicum）的PI127826品系会释放多种倍半萜。为了鉴定参与这些挥发性倍半萜合成的萜合成酶，我们使用大规模平行测序（RNA-seq）获得了这些植物茎毛的转录组。这种方法最初发现了番茄（S. lycopersicum）的6个倍半萜合成酶cDNA和哈勃罗切特番茄（S. habrochaites）的5个倍半萜合成酶cDNA。通过对其他数据库和番茄（S. lycopersicum）基因组的搜索，又发现了2个在茎毛中表达的倍半萜合成酶。番茄（S. lycopersicum）和哈勃罗切特番茄（S. habrochaites）的倍半萜合成酶具有高度的蛋白质同源性。其中一些似乎编码无功能的蛋白质。功能性重组蛋白从（E,E）-法呢基二磷酸酯中产生香豆素、β-石竹烯/α-胡莫烯、绿花烯和瓦伦烯。然而，这些酶的活性并不能完全解释两种番茄植物在倍半萜合成方面的差异。RT-qPCR证实了番茄（S. ly
• Termite Trail Attractants: New Syntheses of Racemic (<i>E</i>)-<i>α</i>-, (<i>Z</i>)-<i>α</i>- and<i>β</i>-Bisabolenes
  作者：Laura Argenti、Fabio Bellina、Adriano Carpita、Nicola Dell'Amico、Renzo Rossi

  DOI：10.1080/00397919408010239

  日期：1994.12

  Racemic (E)-alpha-bisabolene (E)(1) was synthetized starting from 4-methyl-3-cyclohexenecarboxylic acid (3) by a reaction sequence involving the Pd(0)-catalyzed cross-coupling reaction between the (E)-2-methyl-1-alkenyltrimethylstannane 8 and 3-methyl-2-buten-1-yl acetate (9). Three different procedures, in which a common precursor was used as key intermediate, were tested for the synthesis of racemic (Z)-alpha-bisabolene (Z)(1). The best one, which involved the reaction between bromide 18 and lithium dialkenylcuprate 19, afforded a mixture of (Z)- and (E)-1 in a 93:7 molar ratio, respectively. Finally, racemic beta-bisabolene (2) was synthetized by a simple reaction sequence involving the Zr-promoted methylenation of ketone 22 prepared from 3.