trans-pyranoid linalool oxide | 39028-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: trans-pyranoid linalool oxide
• 英文别名: cis-2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol；2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol；linalool trans-oxide；(3R,6S)-6-ethenyl-2,2,6-trimethyloxan-3-ol
• CAS: 39028-58-5
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: BCTBAGTXFYWYMW-PSASIEDQSA-N

物化性质

• 沸点：
  224.2±40.0 °C(Predicted)
• 密度：
  0.988±0.06 g/cm3(Predicted)
• LogP：
  1.461 (est)
• 保留指数：
  1167;1149.2

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-pyranoid linalool oxide 生成 2H-吡喃-3-醇,6-乙烯基四氢-2,2,6-三甲基-,(3S,6R)-
  参考文献：
  名称：

  Resolution of racemic linalool oxide-pyranoid by microbial esterification

  摘要：

  Resolution of racemic cis and trans-linalool oxide-pyranoid via esterification with malonic acid by Glomerella cingulata is described. The enantiomerically pure alcohols and malonic esters can be obtained.

  DOI：

  10.1016/0957-4166(95)00126-a
• 作为产物：
  描述：

  芳樟醇 在 单过氧邻苯二甲酸 、 硫酸酯 、 碳酸氢钠 、 zirconium(IV) oxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.5h， 生成 trans-pyranoid linalool oxide
  参考文献：
  名称：

  摘要：

  The behavior of epoxides of linalool and cis-nerolidyl acetate was comparatively investigated in acids of various strength with the goal of establishing the effect of the structure of the initial c compound and the medium character on the main direction of cationoid rearranuement. Linalool epoxidcS undergo cyclization, of solid acid catalysts affording oxygen-containing heterocyclic Compounds whereas the nerolidyl acetate epoxides yield the ketones originating from the opening of the epoxy ring followed by 1,2-hydride shift. 10,11-Epoxy derivative of cis-nerolidyl acetate affords 7-oxanorbornane as a minor product.

  DOI：

  10.1023/a:1016538920756

文献信息

• Biotransformations of Terpenes by Fungi from Amazonian<i>Citrus</i>Plants
  作者：Maria Gabriela Moreno Rueda、Alessandra Guerrini、Pier Paolo Giovannini、Alessandro Medici、Alessandro Grandini、Gianni Sacchetti、Paola Pedrini

  DOI：10.1002/cbdv.201300112

  日期：2013.10

  The biotransformations of (RS)-linalool (1), (S)-citronellal (2), and sabinene (3) with fungi isolated from the epicarp of fruits of Citrus genus of the Amazonian forest (i.e., C. limon, C. aurantifolia, C. aurantium, and C. paradisiaca) are reported. The more active strains have been characterized, and they belong to the genus Penicillium and Fusarium. Different biotransformation products have been

  （RS）-芳樟醇（1），（S）-香茅醛（2）和sa香烯（3）的生物转化是从亚马逊森林柑橘类水果的果皮（即C. limon，C.报道了桔梗，极光梭菌和天堂梭状芽胞杆菌。已经鉴定了更具活性的菌株，它们属于青霉属和镰刀菌属。取决于真菌和底物，已经获得了不同的生物转化产物。（RS）-Linalool（1）与镰刀菌属（Fusarium sp。）一起提供了（E）-和（Z）-呋喃萘酚氧化物（分别为7和8，分别为39和37％的产率）。（1D2），6-甲基庚-5-烯-2-酮（4; 49％）与藤蔓镰刀菌和1-甲基-1-（4-甲基戊基）环氧乙烷甲醇（6; 42％）与同心镰刀菌。（S）-香茅醛（2）得到镰刀菌属物种的（S）-香茅酚（12; 36-76％）和（S）-香茅酸（11; 5-43％），而非对映异构体对薄荷脑3，与青霉一起获得了作为主要产物的8-二醇13和14（产率分别为20％和50％）。最后，镰刀菌属物种和P
• Palladium(0)-catalysed synthesis of cis - and trans -linalyl oxides
  作者：Christelle Fournier-Nguefack、Paul Lhoste、Denis Sinou

  DOI：10.1016/s0040-4020(97)00130-0

  日期：1997.3

  Linalyl oxides are obtained from (Z)- or (E)-6,7-dihydroxy-3,7-dimethyl-oct-2-enyl carbonate in the presence of Pd2(dba)3 in association with various ligands.

  在Pd 2（dba）3与各种配体结合存在下，由（Z）-或（E）-6,7-二羟基-3,7-二甲基-辛-2-烯基碳酸酯获得芳樟醇氧化物。
• From rational octahedron design to reticulation serendipity. A thermally stable rare earth polymeric disulfonate family with CdI2-like structure, bifunctional catalysis and optical properties
  作者：Natalia Snejko、Concepción Cascales、Berta Gomez-Lor、Enrique Gutiérrez-Puebla、Marta Iglesias、Caridad Ruiz-Valero、M. Angeles Monge

  DOI：10.1039/b202639b

  日期：2002.6.19

  A new family of lanthanide disulfonates Ln(OH)(NDS)(H2O), (Ln = La, Pr and Nd; NDS=1,5-naphthalenedisulfonate) was designed and hydrothermally synthesized; this is the first example of a disulfonate ligand coordinated to six different Ln atoms; these materials, with high thermal stability, act as active and selective bifunctional catalysts in oxidation and epoxide ring opening; strong luminescence from the optically active Nd center was observed.

  一种新的镧系元素二磺酸盐家族 Ln(OH)(NDS)(H2O)（Ln = La、Pr 和 Nd；NDS = 1,5-萘二磺酸盐）被设计并通过水热法合成；这是第一个配位六种不同镧系元素原子的二磺酸配体的例子；这些材料具有高热稳定性，在氧化和环氧开环反应中作为活性和选择性双功能催化剂；观察到来自光学活性 Nd 中心的强荧光。
• Diastereoselective Titanocene-Catalyzed Oxidative Cyclization of Bishomoallylic Alcohols
  作者：Alessandra Lattanzi、Giorgio Della Sala、Maurizio Russo、Arrigo Scettri

  DOI：10.1055/s-2001-16779

  日期：——

  Bishomoallylic alcohols are converted in good yields and diastereoselectivity into tetrahydrofuranols and tetrahydropyranols by Cp2TiCl2/t-butyl hydroperoxide/activated 4 Å molecular sieves system.

  Bishomo醇在Cp2TiCl2/t-丁基过氧化氢/活化的4 Å分子筛体系中以良好的产率和立体选择性转化为四氢呋喃醇和四氢吡喃醇。
• One-pot synthesis at room temperature of epoxides and linalool derivative pyrans in monolacunary Na₇PW₁₁O₃₉-catalyzed oxidation reactions by hydrogen peroxide
  作者：Castelo B. Vilanculo、Márcio J. Da Silva、Milena Galdino Teixeira、Jesus Avendano Villarreal

  DOI：10.1039/d0ra00047g

  日期：——

  new one-pot synthesis route of valuable linalool oxidation derivatives (i.e., 2-(5-methyl-5-vinyltetrahydrofuran-2-yl propan-2-ol) (1a)), 2,2,6-trimethyl-6-vinyltetrahydro-2H-pyran-3-ol (1b) and diepoxide (1c), using a green oxidant (i.e., hydrogen peroxide) under mild conditions (i.e., room temperature). Lacunar Keggin heteropolyacid salts were the catalysts investigated in this reaction. Among them

  在这项工作中，我们描述了一种有价值的芳樟醇氧化衍生物（即2-(5-methyl-5-vinyltetrahydrofuran-2-yl propan-2-ol) ( 1a )）、2,2、 6-trimethyl-6-vinyltetrahydro-2 H -pyran- 3-ol ( 1b ) 和二环氧化物 ( 1c )，在温和条件下（即室温）使用绿色氧化剂（即过氧化氢）。Lacunar Keggin 杂多酸盐是该反应中研究的催化剂。其中，Na 7 PW 11 O 39对氧化产物最具活性和选择性。通过FT-IR、TG/DSC、BET、XRD分析和电位滴定对所有催化剂进行了表征。评估主要反应参数。特别注意将催化剂的组成和性质与其活性相关联。