cis-5-ethenyltetrahydro-α,α,5-trimethyl-2-furan methanol | 23007-29-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: cis-5-ethenyltetrahydro-α,α,5-trimethyl-2-furan methanol
• 英文别名: cis-5-ethenyltetrahydro-α,α,5-trimethyl-2-furanmethanol；(2R,5S)-5-(1-Hydroxy-1-methylethyl)-2-methyl-2-vinyltetrahydrofuran；cis-2-(1-hydroxy-1-methylethyl)-5-methyl-5-vinyltetrahydrofuran；2-((2S,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)propan-2-ol；2-((5R)-tetrahydro-5-methyl-5-vinylfuran-2-yl)propan-2-ol；trans-linalool oxide；Linalool oxide B；2-[(2S,5R)-5-ethenyl-5-methyloxolan-2-yl]propan-2-ol
• CAS: 23007-29-6
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: BRHDDEIRQPDPMG-WPRPVWTQSA-N

物化性质

• 沸点：
  222.6±23.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)
• 保留指数：
  1513

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 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：

  cis-5-ethenyltetrahydro-α,α,5-trimethyl-2-furan methanol 在 ruthenium trichloride 、 sodium periodate 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 生成
  参考文献：
  名称：

  Vanadium(V)-Catalyzed Oxidation of (3R)-Linalool - The Selective Formation of Furanoid Linalool Oxides and their Conversion into Isocyclocapitelline Derivatives

  摘要：

  如果用钒 (V) 希夫碱配合物 4 催化，(3R)-芳樟醇 (2) 与叔丁基过氧化氢 (TBHP) 的氧化作用发生在 6,7-位，选择性地得到芳樟醇氧化物 cis-1。 取代的四氢呋喃顺式-1 及其异构体 trans-1 作为β-咔啉顺式-3 和反式3 的简短合成的起始材料，它们是生物碱(-)-isocyclocapitelline 和(+)-cyclocapitelline 的低级同系物。

  DOI：

  10.1055/s-2003-36793
• 作为产物：
  描述：

  (R)-芳樟醇 在 间氯过氧苯甲酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 cis-5-ethenyltetrahydro-α,α,5-trimethyl-2-furan methanol
  参考文献：
  名称：

  来自番木瓜果实的 6,7-环氧芳樟醇和相关的含氧萜类化合物

  摘要：

  摘要 通过 HRGC 和 HRGC-MS 研究了源自木瓜果实挥发物主要成分芳樟醇的氧化萜类化合物。使用适用于分离和富集极性化合物的样品制备技术，6,7-环氧芳樟醇、2,6-二甲基-octa-1,7-二烯-3,6-二醇、2,6 的两种非对映异构体-二甲基-辛基-3,7-二烯-2,6-二醇、(E)-和(Z)-2,6-二甲基-辛基-2,7-二烯-1,6-二醇和2,6-确定了二甲基-oct-7-ene-2,3,6-triol。此外，首次检测到呋喃和吡喃形式的四种非对映异构环氧-芳樟醇氧化物中的每一种作为天然植物成分。讨论了氧化芳樟醇衍生物的形成和代谢的生物遗传途径。

  DOI：

  10.1016/s0031-9422(00)81287-x

文献信息

• (Schiff-base)vanadium(V) Complex-Catalyzed Oxidations of Substituted Bis(homoallylic) Alcohols − Stereoselective Synthesis of Functionalized Tetrahydrofurans
  作者：Jens Hartung、Simone Drees、Marco Greb、Philipp Schmidt、Ingrid Svoboda、Hartmut Fuess、Alexander Murso、Dietmar Stalke

  DOI：10.1002/ejoc.200200644

  日期：2003.7

  Vanadium(V) complexes 4 have been prepared from tridentate Schiff-base ligands 3 and VO(OEt)3. All vanadium(V) compounds were characterized (IR, UV/Vis, and 51V NMR spectroscopy, and in selected examples by X-ray diffraction analysis) and were applied as oxidation catalysts for the stereoselective synthesis of functionalized tetrahydrofurans 2 starting from substituted bis(homoallylic) alcohols 1 (mono-

  钒 (V) 配合物 4 已由三齿席夫碱配体 3 和 VO(OEt)3 制备。对所有钒 (V) 化合物进行了表征（IR、UV/Vis 和 51V NMR 光谱，在选定的实施例中通过 X 射线衍射分析）并用作氧化催化剂，用于从取代的双 ( homoallylic) 醇 1（单或三取代的 C-C 双键）。在优化条件下氧化仲或叔 1-烷基-、1-乙烯基-或 1-苯基取代的 5,5-二甲基-4-戊烯-1-醇 [TBHP 作为主要氧化剂和 1,2-(氨基)茚满醇衍生的钒（V）试剂 4g 作为催化剂]以合成有用的产率和非对映选择性（22-96% de）提供了 2,5-顺式配置的四氢呋喃。另一方面，从 2- 或 3- 烷基-和 2- 或 3-苯基-取代的 5,5-二甲基-4-戊烯-1-醇双（高烯丙）醇的氧化获得反式二取代的氧杂环戊烷 (62%−96 de) . 用 TBHP 和催化量的钒 (V) 配合物 4g
• A protecting-group-free synthesis of arbusculone, andirolactone, pinnatolide, ipomolactone, cyclocapitelline and isocyclocapitelline
  作者：Srinivas Gajula、Madasu Madhu、Suresh Kumar Chintakrinda、J.S. Yadav、Debendra K. Mohapatra

  DOI：10.1016/j.tetlet.2018.10.024

  日期：2018.11

  A general approach for a collective synthesis of natural products containing substituted THF ring is described. In this paper, Arbusculone, a small molecule natural product accomplished using a short route, is used as the key intermediate to achieve the total synthesis of Andirolactone, Pinnatolide, Ipomolactone, Cyclocapitelline, Isocyclocapitelline and their two isomers in less than ten steps. The

  描述了用于集体合成含有取代的THF环的天然产物的一般方法。在本文中，使用短路径完成的小分子天然产物Arbusculone被用作关键中间体，可在不到十个步骤的情况下完成Andirolactone，Pinnatolide，Ipomolactone，Cyclocapitelline，Isocyclocapitelline及其两个异构体的全合成。目前的工作着重强调了无保护基团的全部合成方法，以及从市售廉价原料中获得这些天然产物的最短途径。
• Synthesis of All Four Stereoisomers of Enantiomerically Pure<i>cis</i>- and<i>trans</i>-Linalyl Oxides
  作者：A. Méou、N. Bouanah、A. Archelas、X. M. Zhang、R. Guglielmetti、R. Furstoss

  DOI：10.1055/s-1990-27003

  日期：——

  The four enantiomerically pure cis- and trans-linalyl oxides can be prepared in one step and good yield from (6S)- or (6R)-6,7-dihydroxygeranyl phenylcarbamate.

  以 (6S)- 或 (6R)-6,7- 二羟基苯丙氨酰苯基氨基甲酸酯为原料，可一步制备出四种对映体纯度较高的顺式和反式芳樟基氧化物。
• cis-2,6-Bis-(methanolate)-piperidine oxovanadium(V) complexes as catalysts for oxidative alkenol cyclization by tert-butyl hydroperoxide
  作者：Maike Dönges、Matthias Amberg、Georg Stapf、Harald Kelm、Uwe Bergsträßer、Jens Hartung

  DOI：10.1016/j.ica.2014.02.007

  日期：2014.8

  cis-2,6-Bis-(methanolate)-piperidine oxovanadium(V) complexes are Lewis acids able to catalyze oxidative cyclization of alkenols by tert-butyl hydroperoxide (TBHP). Terminal dimethyl-substituted (prenyl-type) 4-pentenols bearing an alkyl or a phenyl group in position 1 afford under such conditions 2,5-cis-derivatives of 2-(tetrahydrofuran-2-yl)-2-propanol as major and tetrahydropyran-3-ols as minor products (four examples). Oxidizing 1-phenyl-6-methylhept-5-en-l-ol yields a 75125-mixture of the derived 2-(tetrahydropyran-2-yl)-2-propanol and an oxepan-3-ol, whereas 2-propenols give epoxides in up to 94% yield. Epoxidizing geraniol by TBHP in the presence of a vanadium catalyst prepared from (2,5,6R)-2-diphenylmethanol-6-hydroxymethylpiperidine occurs enantioselectively. Highfield shifts of vanadium-51 resonances upon adding alkyl hydroperoxides to solutions of cis-2,6-bis-(methanolate)-piperidine vanadium(V) complexes point to vanadium(V) tert-butyl peroxy complex formation as key step for activating peroxides. (C) 2014 Elsevier B.V. All rights reserved.
• Antimalarial Properties of Simplified Kalihinol Analogues
  作者：Mary Elisabeth Daub、Jacques Prudhomme、Choukri Ben Mamoun、Karine G. Le Roch、Christopher D. Vanderwal

  DOI：10.1021/acsmedchemlett.7b00013

  日期：2017.3.9

  Several kalihinol natural products, members of the broader isocyanoterpene family of antimalarial agents, are potent inhibitors of Plasmodium falciparum, the agent of the most severe form of human malaria. Our previous total synthesis of kalihinol B provided a blueprint to generate many analogues within this family, some as complex as the natural product and some much simplified and easier to access. Each analogue was tested for blood-stage antimalarial activity using both drug-sensitive and -resistant P. falciparum strains. Many considerably simpler analogues of the kalihinols retained potent activity, as did a compound with a different decalin scaffold made in only three steps from sclareolide. Finally, one representative compound showed reasonable stability toward microsomal metabolism, suggesting that the isonitrile functional group that is critical for activity is not an inherent liability in these compounds.