1,3(15),10-bisabolatriene | 196402-66-1

• 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: 1,3(15),10-bisabolatriene
• 英文别名: β-sesquiphellandrene；beta-Zingiberene；3-[(2R)-6-methylhept-5-en-2-yl]-6-methylidenecyclohexene
• CAS: 196402-66-1
• 化学式: C₁₅H₂₄
• 分子量: 204.356
• InChiKey: PHWISBHSBNDZDX-GICMACPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 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：

  1,3(15),10-bisabolatriene 在 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到alpha-姜黄烯
  参考文献：
  名称：

  Enantiospecific total synthesis of (+)-laevigatin

  摘要：

  The first enantiospecific, total synthesis of (+)-laevigatin from (+)-citronellal is described. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00284-x
• 作为产物：
  描述：

  (3R)-α-methylene-3,7-dimethyl-6-octen-1-al 在 正丁基锂 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 1,3(15),10-bisabolatriene
  参考文献：
  名称：

  Enantiospecific total synthesis of (+)-laevigatin

  摘要：

  The first enantiospecific, total synthesis of (+)-laevigatin from (+)-citronellal is described. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00284-x

文献信息

• Sesquiterpene Synthases Cop4 and Cop6 from Coprinus cinereus: Catalytic Promiscuity and Cyclization of Farnesyl Pyrophosphate Geometric Isomers
  作者：Fernando Lopez-Gallego、Sean A. Agger、Daniel Abate-Pella、Mark D. Distefano、Claudia Schmidt-Dannert

  DOI：10.1002/cbic.200900671

  日期：——

  Cyclization of FPP: Two new fungal sesquiterpene synthase are described that have opposite catalytic fidelities in the cyclization of farnesyl diphosphate. Catalytic promiscuity can be drastically reduced by changing the conditions of the reaction. Conversion of the FPP geometric isomers was found to proceed via opposite enantiomers of a cyclic carbocation intermediate that are rearranged to different

  FPP 的环化：描述了两种新的真菌倍半萜烯合酶，它们在二磷酸法呢酯的环化中具有相反的催化保真度。通过改变反应条件可以大大减少催化混杂。发现 FPP 几何异构体的转化是通过环状碳阳离子中间体的相反对映异构体进行的，这些对映异构体重新排列成不同的倍半萜烯产物。
• [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.
• Enantiospecific total synthesis of (+)-laevigatin
  作者：Subhash P. Chavan、Vijay D. Dhondge、Sachindra S. Patil、Y.Tripura Subba Rao、Chitra A. Govande

  DOI：10.1016/s0957-4166(97)00284-x

  日期：1997.8

  The first enantiospecific, total synthesis of (+)-laevigatin from (+)-citronellal is described. (C) 1997 Published by Elsevier Science Ltd.