4-[(1S)-1,5-dimethylhex-4-enyl]-1-methyl-cyclohex-2-en-1-ol | 343964-36-3

• 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: 4-[(1S)-1,5-dimethylhex-4-enyl]-1-methyl-cyclohex-2-en-1-ol
• 英文别名: 1-methyl-4-[(2S)-6-methylhept-5-en-2-yl]cyclohex-2-en-1-ol
• CAS: 343964-36-3
• 化学式: C₁₅H₂₆O
• 分子量: 222.371
• InChiKey: VVCHIOKYQRUBED-NFOMZHRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-[(1S)-1,5-dimethylhex-4-enyl]-1-methyl-cyclohex-2-en-1-ol 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 反应 3.0h， 以74.5%的产率得到cis-(7S)-10,11-epoxy-1-bisabolen-3-ol
  参考文献：
  名称：

  来自丑角虫 Murgantia histrionica 的雄性特异性聚集信息素的鉴定、合成和生物测定。

  摘要：

  性成熟的雄性丑角产生一种性别特异性化合物，被确定为倍半萜环氧醇 4-[3-(3,3-二甲基环氧乙烷-2-基)-1-甲基丙基]-1-甲基环己基-2-的立体异构体之一en-1-ol（以下称为 murgantiol），一种具有四个手性中心和 16 种可能的立体异构体的化合物。该化合物的产量在中午最高。单独容器中的单个处女雄虫比成群的处女雄虫产生化合物的速率更高。通过合成几种混合物来验证碳骨架，这些混合物总共包含所有可能的异构体，其中一种与昆虫产生的化合物相匹配。昆虫产生的化合物的相对和绝对构型仍有待确定。在实验室生物测定中，

  DOI：

  10.1007/s10886-007-9415-x
• 作为产物：
  描述：

  (-)-香茅醛 在 四丁基氢氧化铵 、 三甲基硅烷基二乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 生成 4-[(1S)-1,5-dimethylhex-4-enyl]-1-methyl-cyclohex-2-en-1-ol
  参考文献：
  名称：

  姜黄烯醇（1 S，4 R，1 'S）-4-（1'，5'-二甲基己基-4'-烯基）-1-甲基环己基-2-烯-1-醇，经鉴定为由以下物质产生的性信息素稻臭臭虫Oebalus poecilus（Heteroptera：Pentatomidae）的雄性

  摘要：

  使用嗅觉仪进行的生物测定表明，东方豹油雄性产生性信息素，化学分析表明该化合物为姜油烯醇。两组异构体，每个异构体包含四个非对映异构体（1 RS，4 RS，1 'S）-和（1 RS，4 RS，1'R）-姜油烯醇。这些非对映异构体未在手性GC色谱柱上分离。因此，为了确定雄性产生的姜丁烯醇的碳1、4和1'的绝对构型，进行了以下策略。将含有雄性挥发物的提取物进行脱水微化学反应，生成姜丁烯，通过手性GC分析分离异构体，并与姜油中的天然姜丁烯进行比较，确定碳4和1'的绝对立体化学为从槲皮酚的13 C NMR谱图分别确定R和S以及碳1为R。最后，生物测定表明，O。poecilus女性对外消旋混合物和（1 RS，4 RS，1 'S）-姜黄烯醇反应。

  DOI：

  10.1021/jf402765b

文献信息

• Total synthesis of bisabolane sesquiterpenoids, α-bisabol-1-one, curcumene, curcuphenol and elvirol: utility of catalytic enamine reaction in cyclohexenone synthesis
  作者：Hisahiro Hagiwara、Tomoyuki Okabe、Hiroki Ono、Vijayendra P. Kamat、Takashi Hoshi、Toshio Suzuki、Masayoshi Ando

  DOI：10.1039/b200629b

  日期：2002.3.25

  Total syntheses of α-bisabol-1-one, curcumene, curcuphenol and elvirol have been accomplished via 1,4-conjugate addition of intact aldehydes to vinyl ketones followed by an intramolecular aldol condensation.

  已经通过将完整的醛与烯烃酮进行1,4互补加成，随后进行分子内醛醇缩合，实现了α-大马士革烯-1-酮、姜烯、姜苯醇和艾维醇的全合成。
• [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。
• Deciphering the Absolute Configuration of Murgantiol Isomers in the Pheromone Blend of the Rice Stink Bug, <i>Mormidea v‐luteum</i> (Hemiptera, Pentatomidae)
  作者：João P. A. Souza、Douglas J. Melo、Antonioni A. C. Moliterno、Leonardo Figueiredo、Paulo H. G. Zarbin

  DOI：10.1002/cbdv.202301860

  日期：2024.4

  The males-produced pheromone blend of the Mormidea v-luteum (Hemiptera, Pentatomidae) consists in two isomers of zingiberenol (1) and three of murgantiol (2). While the absolute configuration of the zingiberenol isomers has been described, the configurations of the murgantiol isomers remained unexplored. So, our objective was to identify the absolute configuration of the murgantiol isomers (2 a–c)

  Mormidea v-uteum （半翅目，蝽科）的雄性产生的信息素混合物由两种异构体姜烯醇 ( 1 ) 和三种异构体 murgantiol ( 2 ) 组成。虽然已经描述了姜烯醇异构体的绝对构型，但 murgantiol 异构体的构型仍未被探索。因此，我们的目标是确定信息素混合物中 murgantiol 异构体 ( 2 a – c ) 的绝对构型。为了实现这一目标，我们首先对天然提取物进行脱水，然后进行对映体拆分，结果，三种异构体被鉴定为 (4 R ,1' S )-murgantiol。通过利用所有信息素成分之间固定的顺式和反式关系，我们建立了异构体2a和2b在C-1处的构型为S ，而2c的构型为R。最后，利用微化学Sharples不对称二羟基化和环氧化物闭环，我们确定了环氧化物环的绝对构型。因此，天然异构体2a 、 2b和2c被鉴定为( 1S , 4R ,1 'S , 4'R )-,(
• Catalytic enamine reaction: an expedient 1,4-conjugate addition of naked aldehydes to vinylketones and its application to synthesis of cyclohexenone from Stevia purpurea
  作者：Hisahiro Hagiwara、Tomoyuki Okabe、Keisuke Hakoda、Takashi Hoshi、Hiroki Ono、Vijayendra P Kamat、Toshio Suzuki、Masayoshi Ando

  DOI：10.1016/s0040-4039(01)00247-7

  日期：2001.4

  Naked aldehydes directly add in a 1,4-manner to vinylketones in the presence of 0.2 equiv. of diethylamine in sealed tubes to provide 5-keto aldehydes. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.