[S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene | 159849-08-8

• 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: [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene
• 英文别名: (6S,7R)-1,3,10-bisabolatriene；α-zingiberene；(-)-zingiberene；ent-zingiberene；Zingiberene；alpha-Zingiberene；(5S)-2-methyl-5-[(2R)-6-methylhept-5-en-2-yl]cyclohexa-1,3-diene
• CAS: 159849-08-8
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: KKOXKGNSUHTUBV-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  15
• 可旋转键数：
  4
• 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：

  [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene 、 5-epi-hyperolactone C 在 2-萘乙酮 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以44%的产率得到(2R,3aR,3bS,4S,4'S,7aS,7bS)-4',7-dimethyl-4-((R)-6-methylhept-5-en-2-yl)-7b-phenyl-4'-vinyl-3a,3b,4,4',5,5',7a,7b-octahydro-2'H,3H-spiro[benzo[3,4]cyclobuta[1,2-b]furan-2,3'-furan]-2',3-dione
  参考文献：
  名称：

  Biyouyanagin B的全合成和结构修正

  摘要：

  对新报道的 biyouyanagin B的有趣追逐导致其从1'到1 的全合成和结构修改。

  DOI：

  10.1002/chem.201001474
• 作为产物：
  描述：

  (+)-香茅醛 在 3,4-二羟基苯甲酸乙酯 氢氧化钾 、 四丁基氢氧化铵 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 34.25h， 生成 [S-(R*,S*)]-5-(1,5-dimethylhexen-4-yl)-2-methyl-1,3-cyclohexa-1,3-diene
  参考文献：
  名称：

  Biyouyanagin A的全合成和修订结构。

  摘要：

  DOI：

  10.1002/anie.200701552

文献信息

• Construction of Two Vicinal Quaternary Carbons by Asymmetric Allylic Alkylation: Total Synthesis of Hyperolactone C and (−)-Biyouyanagin A
  作者：Chao Du、Liqi Li、Ying Li、Zhixiang Xie

  DOI：10.1002/anie.200902908

  日期：2009.10.5

  Call on triple A: Palladium‐catalyzed asymmetric allylic alkylation (Pd‐AAA; see scheme) has enabled a concise and efficient synthesis of hyperolactone C and (−)‐biyouyanagin A in only six (20 % overall yield) and seven (8 % overall yield) steps, respectively. The enantiomers of these natural products were also prepared by exploiting the same methodology.

  呼吁三A：钯催化的不对称烯丙基烷基化（Pd-AAA;参见方案）使得高内酯C和（-）-双油烟精A的简明而高效的合成仅六种（总收率20％）和七种（8％）总产量）步骤。这些天然产物的对映异构体也采用相同的方法制备。
• Total Synthesis, Revised Structure, and Biological Evaluation of Biyouyanagin A and Analogues Thereof
  作者：K. C. Nicolaou、T. Robert Wu、David Sarlah、David M. Shaw、Eric Rowcliffe、Dennis R. Burton

  DOI：10.1021/ja802805c

  日期：2008.8.1

  compounds. The total synthesis proceeded through cascade sequences that efficiently produced enantiomerically pure key building blocks 15b (ent-zingiberene) and 18 (hyperolactone C) and featured a novel [2 + 2] photoinduced cycloaddition reaction which occurred with complete regio- and stereoselectivity. Biological investigations with the synthesized biyouyangagins A (2-11) and hyperolactones C (12-16) revealed

  从金丝桃属植物 H. chinese L. var. 中分离。在 NMR 光谱分析的基础上，杨柳、biyouyanagin A 被指定为结构 1a 或 1b。这种新型天然产物表现出显着的抗 HIV 特性并抑制脂多糖诱导的细胞因子产生。本文描述了 biyouyanagin A 和几种类似物 (3-11) 的全合成、biyouyanagin A 到 2b 的结构修订，以及所有合成化合物的生物学特性。全合成通过级联序列进行，该序列有效地产生对映体纯的关键构建块 15b（ent-zingiberene）和 18（超内酯 C），并具有新颖的 [2 + 2] 光诱导环加成反应，该反应具有完全的区域和立体选择性。
• [EN] COMPOSITIONS AND METHODS TO ATTRACT THE BROWN MARMORATED STINK BUG (BMSB), HALYOMORPHA HALYS<br/>[FR] COMPOSITIONS ET PROCÉDÉS POUR ATTIRER LES PUNAISES MARBRÉES BRUNES (BMSB), HALYOMORPHA HALYS
  申请人：US AGRICULTURE

  公开号：WO2013090703A1

  公开（公告）日：2013-06-20

  A composition (useful for attracting Halyomorpha halys) containing (3R,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, and optionally a carrier material or carrier. The composition may also contain (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol where the composition contains a 3:1 ratio of cis-epoxybisabolenols : trans-epoxybisabolenols produced from (R)-citronellal. These compositions were based on the newly discovered aggregation pheromone components: (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol. The composition may also contain methyl (2E,4E,6Z)-decatrieonate. Also a method for attracting Halyomorpha halys to an object or area, involving treating said object or area with a Halyomorpha halys attracting composition containing a Halyomorpha halys attracting effective amount of the composition.

  一种吸引半环纹椿象的组合物，包含（3R,6R,7R,10S）-10,11-环氧-1-双萜-3-醇，（3R,6R,7R,10R）-10,11-环氧-1-双萜-3-醇，（3S,6S,7R,10S）-10,11-环氧-1-双萜-3-醇，（3S,6S,7R,10R）-10,11-环氧-1-双萜-3-醇，以及可选的载体材料或载体。该组合物还可以包含（3R,6S,7R,10S）-10,11-环氧-1-双萜-3-醇，（3R,6S,7R,10R）-10,11-环氧-1-双萜-3-醇，（3S,6R,7R,10S）-10,11-环氧-1-双萜-3-醇，（3S,6R,7R,10R）-10,11-环氧-1-双萜-3-醇，其中该组合物包含从（R）-柠檬醛产生的顺式环氧双萜醇和反式环氧双萜醇的3:1比例。这些组合物基于新发现的聚集信息素成分：（3S,6S,7R,10S）-10,11-环氧-1-双萜-3-醇和（3R,6S,7R,10S）-10,11-环氧-1-双萜-3-醇。该组合物还可以含有甲基（2E,4E,6Z）-癸三烯酸甲酯。还提供了一种吸引半环纹椿象到物体或区域的方法，涉及使用含有半环纹椿象吸引有效量的吸引组合物处理所述物体或区域。
• Discovery of the Aggregation Pheromone of the Brown Marmorated Stink Bug (<i>Halyomorpha halys</i>) through the Creation of Stereoisomeric Libraries of 1-Bisabolen-3-ols
  作者：Ashot Khrimian、Aijun Zhang、Donald C. Weber、Hsiao-Yung Ho、Jeffrey R. Aldrich、Karl E. Vermillion、Maxime A. Siegler、Shyam Shirali、Filadelfo Guzman、Tracy C. Leskey

  DOI：10.1021/np5003753

  日期：2014.7.25

  We describe a novel and straightforward route to all stereoisomers of 1,10-bisaboladien-3-ol and 10,11-epoxy-1-bisabolen-3-ol via the rhodium-catalyzed asymmetric addition of trimethylaluminum to diastereomeric mixtures of cyclohex-2-enones 1 and 2. The detailed stereoisomeric structures of many natural sesquiterpenes with the bisabolane skeleton were previously unknown because of the absence of stereoselective syntheses of individual stereoisomers. Several of the bisabolenols are pheromones of economically important pentatomid bug species. Single-crystal X-ray crystallography of underivatized triol 13 provided unequivocal proof of the relative and absolute configurations. Two of the epoxides, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (3) and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol (4), were identified as the main components of a male-produced aggregation pheromone of the brown marmorated stink bug, Halyomorpha halys, using GC analyses on enantioselective columns. Both compounds attracted female, male, and nymphal H. halys in field trials. Moreover, mixtures of stereoisomers containing epoxides 3 and 4 were also attractive to H. halys, signifying that the presence of additional stereoisomers did not hinder attraction of H. halys and relatively inexpensive mixtures can be used in monitoring, as well as control strategies. H. halys is a polyphagous invasive species in the U.S. and Europe that causes severe injury to fruit, vegetables, and field crops and is also a serious nuisance pest.
• Total Synthesis and Revised Structure of Biyouyanagin A
  作者：K. C. Nicolaou、David Sarlah、David M. Shaw

  DOI：10.1002/anie.200701552

  日期：2007.6.18