(+)-trans-piperitol | 65733-28-0

• 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: (+)-trans-piperitol
• 英文别名: (-)-L-piperitenol；(3R,4R)-piperitol；trans-piperitol；E-piperitol；isomenthol；(3R)-1-Methyl-4t-isopropyl-cyclohexen-(1)-ol-(3r)；(1R,6R)-3-methyl-6-propan-2-ylcyclohex-2-en-1-ol
• CAS: 65733-28-0
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: HPOHAUWWDDPHRS-ZJUUUORDSA-N

物化性质

• 沸点：
  222.7±19.0 °C(Predicted)
• 密度：
  0.924±0.06 g/cm3(Predicted)
• 保留指数：
  1189;1196;1191;1189;1180;1187;1187;1183;1203;1216;1180;1194;1194;1181;1186;1204;1193;1185;1185;1197;1191;1193;1187;1192;1192;1204;1192;1177;1188;1188;1202;1187;1196;1192;1199.7;1187;1202;1195;1205;1192;1195;1185

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (+)-trans-piperitol 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以49%的产率得到(1S,2R,3R,4R)-1,2-环氧-1-甲基-4-(1-甲基乙基)-环己烷-3-醇
  参考文献：
  名称：

  Gukulenin A的全合成进展：光化学触发的两碳环扩环是α-Tropolonic醚合成的关键

  摘要：

  揭示了从（-）-哌啶酮手性池合成高级gukulenin A前体。合成C 2不对称双（α-tropolonic）醚构件的关键C / C连接方法是收缩环的Meinwald重排，光化学触发的二碳环膨胀和通过交叉复分解的均二聚作用。

  DOI：

  10.1021/acs.orglett.8b01629
• 作为产物：
  描述：

  L-薄荷醇 在 Chlorella vulgaris 作用下， 反应 92.0h， 以92.3%的产率得到(+)-trans-piperitol
  参考文献：
  名称：

  Biotransformation of menthol by Chlorella vulgaris and study of the pathways involved

  摘要：

  DOI：

  10.1007/s10600-014-0849-4

文献信息

• Heterogeneous Hydroxyl-Directed Hydrogenation: Control of Diastereoselectivity through Bimetallic Surface Composition
  作者：Alexander J. Shumski、William A. Swann、Nicole J. Escorcia、Christina W. Li

  DOI：10.1021/acscatal.1c01434

  日期：2021.5.21

  surface. In this work, we demonstrate that Pd–Cu bimetallic nanoparticles with both Pd and Cu atoms distributed across the surface are capable of high conversion and diastereoselectivity in the hydroxyl-directed hydrogenation reaction of terpinen-4-ol. We postulate that the OH directing group adsorbs to the more oxophilic Cu atom while the olefin and hydrogen bind to adjacent Pd atoms, thus enabling selective

  定向氢化反应通常由均相的Rh和Ir络合物催化，其中产物的选择性取决于底物上辅助定向基团与催化剂的结合。由于缺乏对催化剂表面上底物结合取向的控制，没有一种多相催化剂能够达到相当高的方向性。在这项工作中，我们证明了Pd和Cu原子分布在整个表面上的Pd-Cu双金属纳米粒子在萜品烯-4-醇的羟基定向加氢反应中具有很高的转化率和非对映选择性。我们假设OH导向基团吸附到更具亲氧性的Cu原子上，而烯烃和氢键合到相邻的Pd原子上，
• Enzymatic resolution of racemic secondary cyclic allylic alcohols
  作者：Katarzyna Wińska、Aleksandra Grudniewska、Anna Chojnacka、Agata Białońska、Czesław Wawrzeńczyk

  DOI：10.1016/j.tetasy.2010.02.031

  日期：2010.4

  The resolutions of five racemic cyclic alcohols: 6,6-dimethylcyclohex-2-en-1-ol (±)-5, 4,4-dimethylcyclohex-2-en-1-ol (±)-7, 5,5-dimethylcyclohex-2-en-1-ol (±)-11 and isomeric trans-(±)-13 and cis-piperitols (±)-14 are presented. They were resolved by enzymatic esterification with vinyl esters or by enzymatic hydrolysis of their racemic esters in phosphate buffer. The following lipases were used as

  五个外消旋环醇的分辨率：6,6-二甲基环己-2-烯-1-醇（±） - 5，4,4-二甲基环己-2-烯-1-醇（±） - 7，5,5-二甲基环己-2-烯-1-醇（±） - 11和同分异构体的反式- （±） - 13和顺式- piperitols（±） - 14被呈现。通过用乙烯基酯进行酶促酯化反应或通过在磷酸盐缓冲液中酶解其外消旋酯来拆分它们。以下脂肪酶被用作生物催化剂：Novozyme 435（南极假丝酵母），Amano PS（伯克霍尔德酵母）和来自假丝酵母的脂肪酶。获得具有至少96％ee的所有醇异构体。
• Isolation, structural assignment and insecticidal activity of (−)-(1S,2R,3R,4S)-1,2-epoxy-1-methyl-4-(1-methylethyl)-cyclohex-3-yl acetate, a natural product from Minthostachys tomentosa
  作者：Ángel Cantı́n、Cristina Lull、Jaime Primo、Miguel A. Miranda、Eduardo Primo-Yúfera

  DOI：10.1016/s0957-4166(01)00094-5

  日期：2001.3

  (-)-(1S,2R,3R,4S)-1,2-Epoxy-1-methyl-4-(1-methylethyl)-cyclohex-3-yl acetate has previously been identified as the active compound of Minthostachys tomentosa responsible for the insecticidal activity against Oncopeltus fasciatus. Its structure was initially assigned on the basis of spectral data. In order to confirm the structure and to define the stereochemistry, stereoselective synthesis of its enantiomer, (+)-(1R,2S,3S,3R)-1,2-epoxy-1-methyl-4-(1-methylethyl)-cyclohex-3-yl acetate, starting from (R)-(-)piperitone, was carried out using a Sharpless reaction as the key step. The natural product is dextro-rotatory while the synthetic product is levo-rotatory. Measurements of insecticidal activities of the different steroisomers revealed that only the natural product is active. (C) 2001 Elsevier Science Ltd. All rights reserved.

  (-)-(1S,2R,3R,4S)-1,2-环氧-1-甲基-4-(1-甲基乙基)-环己-3-基醋酸酯已被鉴定为保护植物 Against Oncopeltus fasciatus 的斑须蝇植株植物活性成分活性分子。其结构最初是基于光谱数据确定的。为了确认结构并确定立体化学，以 (R)-(-) 芥子酮为起始原料，通过使用Sharpless反应作为关键步骤，成功地进行了其对映体 (+)-(1R,2S,3S,4R)-1,2-环氧-1-甲基-4-(1-甲基乙基)-环己-3-基醋酸酯的立体选择性合成。天然产物是右旋的，而合成产物是左旋的。对不同立体异构体的杀虫活性的测量表明，只有天然产物是具有活性的。© 2001 Elsevier Science Ltd. 保留所有权利。
• Synthesis and Antifeedant Activity of Racemic and Optically Active Hydroxy Lactones with the p-Menthane System
  作者：Aleksandra Grudniewska、Marek Kłobucki、Katarzyna Dancewicz、Maryla Szczepanik、Beata Gabryś、Czesław Wawrzeńczyk

  DOI：10.1371/journal.pone.0131028

  日期：——

  Two racemic and two enantiomeric pairs of new δ-hydroxy-γ-lactones based on the p-menthane system were prepared from racemic and optically active cis- and trans-piperitols. The Johnson-Claisen rearrangement of the piperitols, epoxidation of the γδ-unsaturated esters, and acidic lactonization of the epoxy esters were described. The structures of the compounds were confirmed spectroscopically. The antifeedant activities of the hydroxy lactones and racemic piperitone were evaluated against three insect pests: lesser mealworm, Alphitobius diaperinus (Panzer); Colorado potato beetle, Leptinotarsa decemlineata (Say); and peach-potato aphid, Myzus persicae (Sulz.). The chemical transformation of piperitone by the introduction of a lactone moiety and a hydroxy group changed its antifeedant properties. Behavioral bioassays showed that the feeding deterrent activity depended on the insect species and the structure of the compounds. All hydroxy lactones deterred the settling of M. persicae. Among chewing insects, the highest sensitivity showed A. diaperinus adults.

  两对消旋和两对手性的新δ-羟基-γ-内酯基于p-薄荷烷系统，分别由消旋和光学活性的顺式和反式薄荷醇制备而成。文中描述了薄荷醇的约翰逊-克莱森重排、γδ-不饱和酯的环氧化以及环氧酯的酸性内酯化过程。化合物的结构通过光谱学方法确认。研究了羟基内酯和消旋薄荷酮对三种害虫的抗取食活性：小黄米虫（Alphitobius diaperinus，Panzer）；科罗拉多土豆甲虫（Leptinotarsa decemlineata，Say）；以及桃-土豆蚜虫（Myzus persicae，Sulz.）。通过引入内酯基团和羟基对薄荷酮进行的化学转化改变了其抗取食特性。行为生物测定表明，取食抑制活性依赖于昆虫种类和化合物的结构。所有羟基内酯都能抑制桃-土豆蚜虫的定居。在咀嚼昆虫中，小黄米虫成虫的敏感性最高。
• Process for isomerizing cycloalkenol to cycloalkanone
  申请人：SCM Corporation

  公开号：US04160786A1

  公开（公告）日：1979-07-10

  A beta-, gamma-unsaturated cycloalkenol contaminated with an acid-forming moiety is catalytically isomerized to a cycloalkanone in the presence of copper chromite catalyst and an insoluble base which suppresses the acid-forming moiety during the isomerization.

  在铬酸铜催化剂和不溶性碱的存在下，含有酸性基团的β-，γ-不饱和环己烯醇被催化异构化为环戊酮，并抑制酸性基团在异构化过程中的产生。