(S)-齿小蠹二烯醇

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(S)-齒小蠹二烯醇
Ipsdienol molecule
IUPAC名
(4S)-2-Methyl-6-methylideneocta-2,7-dien-4-ol
別名 (S)-(+)-齒小蠹二烯醇、2-甲基-6-亞甲基-2,7-辛二烯-4-醇
識別
CAS號 35628-00-3  checkY
PubChem 92301
SMILES
 
  • CC(=CC(CC(=C)C=C)O)C
性質
化學式 C10H16O
摩爾質量 152.23 g·mol−1
外觀 Colorless
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

(S)-齒小蠹二烯醇（英語：(S)-Ipsdienol，錯誤譯作小蠢二烯醇），是一種萜烯醇。它是小蠹的主要聚集信息素之一。它首先是從混點齒小蠹（Ips confusionus）中發現的，人們認為它是一種主要的性引誘劑。[1]研究表明，該化合物在北美西部松齒小蠹（Ips latidens）和Ips ini之間的種間通訊中發揮作用，有助於減少繁殖材料的競爭和/或交配干擾。[2]

合成[編輯]

該化合物是由D-甘露醇合成的。[3]通過相應的醛（異戊烯醛）[4]和醇（異戊烯醇）[5]的不對稱異戊烯化實現了替代合成。已發現外消旋前體的手性拆分可提供高對映體純度和製備規模的齒小蠹二烯醇對映體。[6][7]

參考資料[編輯]

  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. （原始內容存檔於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 可免費查閱. 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. （原始內容存檔於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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