2,2,6-trimethyl-6-vinyltetrahydropyran-3-ol | 10448-31-4

• 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: 2,2,6-trimethyl-6-vinyltetrahydropyran-3-ol
• 英文别名: Linalool-monoxid；Linalol oxide pyranoid A；(6R)-6-ethenyl-2,2,6-trimethyloxan-3-ol
• CAS: 10448-31-4；14009-71-3；14049-11-7；22628-11-1；24048-52-0；39028-58-5；41720-62-1
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: BCTBAGTXFYWYMW-HTLJXXAVSA-N

物化性质

• 保留指数：
  1152

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：

  2,2,6-trimethyl-6-vinyltetrahydropyran-3-ol 、 甲基磺酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到Methanesulfonic acid (R)-2,2,6-trimethyl-6-vinyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  The use of acyclic monoterpenes in the preparation of β-pyrones: Synthesis of the right-hand fragment of Usneoidone E

  摘要：

  The right hand fragment, 36, of Usneoidone E, 1, a powerful antiviral and antitumoural agent has been synthesized from the beta-pyrone 32. Using linalool as starting material, a 2,2,6,6-tetrasubstituted dihydropyrane 20, precursor of 32 and 33, was prepared. 20 was also synthesized From geranyl acetate through selenide 7, and is a versatile precursor for the synthesis of tetaprenyltoluquinols. Unambiguous C-13 NMR assignment has been done by 2D correlations.

  DOI：

  10.1016/0040-4020(95)00084-l
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以80%的产率得到2,2,6-trimethyl-6-vinyltetrahydropyran-3-ol
  参考文献：
  名称：

  The use of acyclic monoterpenes in the preparation of β-pyrones: Synthesis of the right-hand fragment of Usneoidone E

  摘要：

  The right hand fragment, 36, of Usneoidone E, 1, a powerful antiviral and antitumoural agent has been synthesized from the beta-pyrone 32. Using linalool as starting material, a 2,2,6,6-tetrasubstituted dihydropyrane 20, precursor of 32 and 33, was prepared. 20 was also synthesized From geranyl acetate through selenide 7, and is a versatile precursor for the synthesis of tetaprenyltoluquinols. Unambiguous C-13 NMR assignment has been done by 2D correlations.

  DOI：

  10.1016/0040-4020(95)00084-l

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
• Vanadium(V)-Catalyzed Oxidation of (3<i>R</i>)-Linalool - The Selective Formation of Furanoid Linalool Oxides and their Conversion into Isocyclocapitelline Derivatives
  作者：Jens Hartung、Simone Drees、Barbara Geiss、Philipp Schmidt

  DOI：10.1055/s-2003-36793

  日期：——

  Oxidation of (3R)-linalool (2) with tert-butyl hydroperoxide (TBHP) occurs at the 6,7-position to selectively afford linalool oxide cis-1, if catalyzed by vanadium(V) Schiff base complexes 4. Substituted tetrahydrofuran cis-1 and its isomer trans-1 served as starting materials for short concise syntheses of β-carbolines cis-3 and trans-3 which are lower homologues of alkaloids (-)-isocyclocapitelline and (+)-cyclocapitelline.

  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。
• The use of acyclic monoterpenes in the preparation of β-pyrones: Synthesis of the right-hand fragment of Usneoidone E
  作者：Julio G. Urones、David Díez、Isidro S. Marcos、Pilar Basabe、Anna M. Lithgow、Rosalina F. Moro、Narciso M. Garrido、Ricardo Escarcena

  DOI：10.1016/0040-4020(95)00084-l

  日期：1995.3

  The right hand fragment, 36, of Usneoidone E, 1, a powerful antiviral and antitumoural agent has been synthesized from the beta-pyrone 32. Using linalool as starting material, a 2,2,6,6-tetrasubstituted dihydropyrane 20, precursor of 32 and 33, was prepared. 20 was also synthesized From geranyl acetate through selenide 7, and is a versatile precursor for the synthesis of tetaprenyltoluquinols. Unambiguous C-13 NMR assignment has been done by 2D correlations.