(1R,3R,4R,8R)-3,9-oxa-p-menthan-8-ol | 832721-39-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (1R,3R,4R,8R)-3,9-oxa-p-menthan-8-ol
• 英文别名: 3,7-dimethyl-9-oxabicyclo[4.3.0]nonan-7-ol；(3R,3aS,6S,7aS)-3,6-dimethyl-3a,4,5,6,7,7a-hexahydro-2H-1-benzofuran-3-ol
• CAS: 832721-39-8
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: TVUVRKMLCJGCND-XKNYDFJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1R,3R,4R,8R)-3,9-oxa-p-menthan-8-ol 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 4.0h， 以40%的产率得到1-[(4S)-2-hydroxy-4-methylcyclohexen-1-yl]ethanone
  参考文献：
  名称：

  Bicyclic β-Hydroxytetrahydrofurans as Precursors of Medium Ring Keto-Lactones

  摘要：

  The reaction of a series of cis-fused bicyclic beta-hydroxytetrahydrofurans with ruthenium tetraoxide, generated in situ from ruthenium trichloride and sodium periodate, afforded 9- and 10-membered keto-lactones in moderate to good yields, in a clean and straightforward fashion. The starting beta-hydroxyethers were obtained from the corresponding 3-alkenols by two alternative procedures, depending on their pattern of substitution: (a) epoxidation by dimethyldioxirane, followed by base-catalyzed cyclization of the resulting epoxyalcohol, and (b) thallium trinitrate-mediated cyclization of the 3-alkenols, a method already described by our group.

  DOI：

  10.1021/jo0626109
• 作为产物：
  描述：

  (1S,3S,4R)-对薄荷-8-烯-3-醇 在 thallium(III) nitrate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 0.08h， 以85%的产率得到(1R,3R,4R,8R)-3,9-oxa-p-menthan-8-ol
  参考文献：
  名称：

  salts（III）盐介导的不饱和单萜醇的环化

  摘要：

  三乙酸th和三硝酸th与四种单萜类不饱和醇（异萜烯醇，新异异薄荷醇，顺式香芹酚和α-松油醇）在AcOH：H 2 O（1：1，vol / vol）中的反应导致相应的具有高区域和立体选择性的β-羟基环醚，产率中等至良好。基于每个双键的取代方式，提出了一种缩醛化的加合物的缩环或扩环机理。

  DOI：

  10.1016/s0040-4039(00)76741-4

文献信息

• Compounds, Compositions and methods for insect control
  申请人：DeLong Anthony Mitchell

  公开号：US20050025795A1

  公开（公告）日：2005-02-03

  Rapidly acting compositions having vapor phase insecticidal activity comprise natural products or natural product-based materials. Further, these materials are non-petroleum based, are typically 100% biodegradable, and typically do not persist in the environment, unlike traditional pesticides. The compositions kill susceptible insects on contact in seconds, even the notoriously hardy peripleneta species. The compositions also kill insects behind cracks and crevices and when sprayed onto absorbent surfaces such as wood and plasterboard, where traditional contact insecticides work poorly or not at all. New methods of testing insecticides can be used to quantify these effects.

  快速作用的具有蒸汽相杀虫活性的组合物包括天然产品或基于天然产品的材料。此外，这些材料不基于石油，通常是100%可生物降解的，并且通常不会在环境中残留，不像传统杀虫剂。这些组合物能在接触时在几秒钟内杀死易感昆虫，甚至是以硬质蟑螂物种而著称的物种。这些组合物还能在裂缝和缝隙后杀死昆虫，并且当喷洒到吸收性表面（如木材和石膏板）时，传统的接触杀虫剂效果不佳或根本不起作用。可以使用新的杀虫剂测试方法来量化这些效果。
• Cyclization of unsaturated monoterpenic alcohols mediated by thallium (III) salts
  作者：Helena M.C. Ferraz、Carlos M.R. Ribeiro、Mônica V.A. Grazini、Timothy J. Brocksom、Ursula Brocksom

  DOI：10.1016/s0040-4039(00)76741-4

  日期：1994.3

  thallium trinitrate with four monoterpenic unsaturated alcohols (isopulegol, neo-isopulegol, cis-carveol and α-terpineol), in AcOH:H2O (1:1, vol/vol) as solvent, led to the corresponding β-hydroxy-cyclic ethers with high regio- and stereoselectivity, in moderate to good yields. A mechanism of ring-contraction or ring-expansion of the oxythallated adduct is proposed, based on the substitution patterns of

  三乙酸th和三硝酸th与四种单萜类不饱和醇（异萜烯醇，新异异薄荷醇，顺式香芹酚和α-松油醇）在AcOH：H 2 O（1：1，vol / vol）中的反应导致相应的具有高区域和立体选择性的β-羟基环醚，产率中等至良好。基于每个双键的取代方式，提出了一种缩醛化的加合物的缩环或扩环机理。
• Bicyclic β-Hydroxytetrahydrofurans as Precursors of Medium Ring Keto-Lactones
  作者：Helena M. C. Ferraz、Luiz S. Longo

  DOI：10.1021/jo0626109

  日期：2007.4.1

  The reaction of a series of cis-fused bicyclic beta-hydroxytetrahydrofurans with ruthenium tetraoxide, generated in situ from ruthenium trichloride and sodium periodate, afforded 9- and 10-membered keto-lactones in moderate to good yields, in a clean and straightforward fashion. The starting beta-hydroxyethers were obtained from the corresponding 3-alkenols by two alternative procedures, depending on their pattern of substitution: (a) epoxidation by dimethyldioxirane, followed by base-catalyzed cyclization of the resulting epoxyalcohol, and (b) thallium trinitrate-mediated cyclization of the 3-alkenols, a method already described by our group.