维基百科

(S)-齿小蠹二烯醇

化合物

(S)-齿小蠹二烯醇（英语：(S)-Ipsdienol，错误译作小蠢二烯醇），是一种萜烯醇。它是小蠹的主要聚集信息素之一。它首先是从混点齿小蠹（Ips confusionus）中发现的，人们认为它是一种主要的性引诱剂。[1]研究表明，该化合物在北美西部松齿小蠹（Ips latidens）和Ips ini之间的种间通讯中发挥作用，有助于减少繁殖材料的竞争和/或交配干扰。[2]

(S)-齿小蠹二烯醇
Ipsdienol molecule
IUPAC名
(4S)-2-Methyl-6-methylideneocta-2,7-dien-4-ol
别名 (S)-(+)-齿小蠹二烯醇、2-甲基-6-亚甲基-2,7-辛二烯-4-醇
识别
CAS号 35628-00-3  checkY
PubChem 92301
SMILES
 
  • CC(=CC(CC(=C)C=C)O)C
性质
化学式 C10H16O
摩尔质量 152.23 g·mol−1
外观 Colorless
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

合成

该化合物是由D-甘露醇合成的。[3]通过相应的醛（异戊烯醛）[4]和醇（异戊烯醇）[5]的不对称异戊烯化实现了替代合成。已发现外消旋前体的手性拆分可提供高对映体纯度和制备规模的齿小蠹二烯醇对映体。[6][7]

参考资料

  1. ^ Silverstein, Robert M.; Rodin, J. Otto; Wood, David L. Sex Attractants in Frass Produced by Male Ips confusus in Ponderosa Pine. Science. October 1966, 154 (3748): 509–510 [2023-10-09]. Bibcode:1966Sci...154..509S. JSTOR 1720044. S2CID 80674108. doi:10.1126/science.154.3748.509. （原始内容存档于2023-10-09）. 
  2. ^ Miller, Daniel R.; Borden, John H.; King, G. G. S.; Slessor, Keith N. Ipsenol: an aggregation pheromone for Ips latidens (Leconte) (Coleoptera: Scolytidae). Journal of Chemical Ecology. 1 August 1991, 17 (8): 1517–1527. PMID 24257877. S2CID 22337300. doi:10.1007/BF00984685. 
  3. ^ Hanessian, Stephen. Total Synthesis of Natural Products: The 'Chiron' Approach. Pergamon press. 1983: 63. ISBN 978-0-08-029247-2. 
  4. ^ Zhang, Yu-Long; He, Bo-Jun; Xie, Yi-Wen; Wang, Yu-Hao; Wang, Yi-Long; Shen, Yong-Cun; Huang, Yi-Yong. Enantioselective Isoprenylboration Reaction of Aldehydes Catalyzed by a Chiral Phosphoric Acid. Advanced Synthesis & Catalysis. 2019, 361 (13): 3074–3079. S2CID 133162412. doi:10.1002/adsc.201900203. 
  5. ^ Xiang, Ming; Luo, Guoshun; Wang, Yuankai; Krische, Michael J. Enantioselective iridium-catalyzed carbonyl isoprenylation via alcohol-mediated hydrogen transfer. Chemical Communications. 2019, 55 (7): 981–984. PMC 6339811  . PMID 30608076. doi:10.1039/C8CC09706B. 
  6. ^ Kovalenko, V. N.; Prokhorevich, K. N. Improved synthesis of optically active ipsdienol. Russian Journal of Organic Chemistry. 2016, 52 (5): 757–758 [2023-10-09]. S2CID 99770908. doi:10.1134/S1070428016050250. （原始内容存档于2022-03-21）. 
  7. ^ Kovalenko, V. N.; Matyushenkov, E. A. Stereoselective synthesis of (R)- and (S)-Ipsdienols, pheromone components of bark beetles of the Ips family. Russian Journal of Organic Chemistry. 2012, 48 (9): 1168–1172. S2CID 84179515. doi:10.1134/S1070428012090035. 
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