2-羟基-6-戊-4-烯基-2H-吡喃-5-酮 | 89567-15-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2-羟基-6-戊-4-烯基-2H-吡喃-5-酮
• 英文名称: 6-hydroxy-2-(pent-4-en-1-yl)-2H-pyran-3(6H)-one
• 英文别名: 6-hydroxy-2-pent-4-enylpyran-3(6H)-one；2-hydroxy-6-pent-4-enyl-2H-pyran-5-one
• CAS: 89567-15-7
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: KIHVZPSKIRTBFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  325.2±42.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-羟基-6-戊-4-烯基-2H-吡喃-5-酮 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  氧化吡啶鎓-烯烃[5 + 2]环加成共轭加成级联（C 3）序列：范围，限制和计算研究

  摘要：

  描述了氧吡啶鎓-烯烃[5 + 2]环加成共轭加成级联（C 3）序列。研究了涉及末端烯烃，烯醛和烯酮的分子内环加成反应。带有不同长度束缚的底物传递了五元和六元碳环和杂环，从而证明了环加成-共轭加成级联反应的范围和局限性。若干实验和理论计算为提出的机制途径提供了证据。

  DOI：

  10.1021/acs.joc.8b01322
• 作为产物：
  描述：

  alpha-戊基呋喃-2-甲醇 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 癸烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 2-羟基-6-戊-4-烯基-2H-吡喃-5-酮
  参考文献：
  名称：

  Unique Reactivity of anti- and syn-Acetoxypyranones en Route to Oxidopyrylium Intermediates Leading to a Cascade Process

  摘要：

  Unique reactivity of anti- and syn-acetoxypyranones was observed in oxidopyrylium-alkene [5 + 2] cycloadditions. The subtle interplay between the corresponding acetoxypyranone conformation and steric bulk of tertiary amine bases causes syn-acetoxypyranones to undergo [5 + 2] cycloaddition appreciably faster than anti-acetoxypyranones. Additionally, the efficiency of a cascade process that afforded a novel tetracyclic lactol was determined to be dependent on the relative stereochemistry of each diastereomer, the amine base utilized, and the addition of water.

  DOI：

  10.1021/ol4012986

文献信息

• A solvent-free catalytic protocol for the Achmatowicz rearrangement
  作者：Guodong Zhao、Rongbiao Tong

  DOI：10.1039/c8gc03030h

  日期：——

  Reported here is the development of an environmentally friendly catalytic (KBr/oxone) and solvent-free protocol for the Achmatowicz rearrangement (AchR). Different from all previous methods is that the use of chromatographic alumina (Al2O3) allows AchR to proceed smoothly in the absence of any organic solvent and therefore considerably facilitates the subsequent workup and purification with minimal

  这里报道的是针对Achmatowicz重排（AchR）的环保型催化（KBr / oxone）和无溶剂方案的开发。与所有以前的方法不同的是，使用色谱氧化铝（Al 2 O 3）可使AchR在不存在任何有机溶剂的情况下顺利进行，因此可极大地促进后续的后处理和纯化，并且对环境的影响最小。重要的是，该协议允许按比例放大（从毫克到克），回收Al 2 O 3以及与其他反应按一锅顺序方式进行整合。
• Preparation and properties of some phytotoxic 2-benzyloxy-8-oxabicyclo[3.2.1]octane derivatives
  作者：Peter G. Sammes、Leslie J. Street、Peter Kirby

  DOI：10.1039/p19830002729

  日期：——

  The preparation and biological activity of a novel group of herbicides is described. These 2-benzyloxy-8-oxabicyclo[3.2.1]octanes are readily obtained from the cycloadducts formed between various olefins and 3-oxidopyrylium ylides, prepared from 6-acetoxypyran-3(6H)-ones.

  描述了新型除草剂的制备和生物学活性。这些2-苄氧基-8-氧杂双环[3.2.1]辛烷很容易从各种烯烃与3-氧氧化吡啶鎓烷基化物之间形成的环加合物获得，所述环氧化物由6-乙酰氧基吡喃-3（6H）-制备。
• Investigation of oxidopyrylium–alkene [5+2] cycloaddition conjugate addition cascade (C³) sequences
  作者：Justin A. Simanis、C. Marshall Law、Erica L. Woodall、Christopher G. Hamaker、John R. Goodell、T. Andrew Mitchell

  DOI：10.1039/c4cc04163a

  日期：——

  Highly diastereoselective oxidopyrylium–alkene [5+2] cycloaddition conjugate addition cascade (C³) sequences providing novel caged ethers are described.

  描述了高度对映选择性的氧代吡啶-烯[5+2]环加成共轭加成级联（C3）序列，提供了新型笼状醚。
• Silica gel enables Achmatowicz rearrangement with KBr/oxone under “anhydrous” condition for one-pot functionalization
  作者：Guodong Zhao、Rongbiao Tong

  DOI：10.1016/j.tet.2018.12.022

  日期：2019.3

  Silica gel was found to effectively promote Achmatowicz rearrangement (AchR) using KBr/oxone under near anhydrous condition. This new protocol allows direct functionalization of AchR products in a one-pot manner, effectively reducing the cost, time, and environmental impacts derived from the conventional stop-and-go approach using separate reaction vessels. These advantages were demonstrated in four

  人们发现，在近乎无水的条件下，使用KBr /恶唑酮可有效促进Achmatowicz重排（AchR）硅胶。这一新协议允许以一锅法将AchR产品直接功能化，有效降低了使用单独的反应容器的常规停停走走方法带来的成本，时间和环境影响。这些优点在四种类型的顺序一锅反应中得到了证明：i）AchR-Kishi还原（和AchR-Ferrier烯丙基化）；ii）AchR-酰化-O-糖基化；iii）AchR-酰化-[5 + 2]-环加成；iv）AchR-TEMPO氧化。
• Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions
  作者：Noah Z. Burns、Michael R. Witten、Eric N. Jacobsen

  DOI：10.1021/ja206997e

  日期：2011.9.21

  A new method for effecting catalytic enantioselective intramolecular [5 + 2] cycloadditions based on oxidopyrylium intermediates is reported. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental evidence points to a new type of cooperative catalysis with each species being necessary to generate a reactive pyrylium ion pair that undergoes subsequent cycloaddition with high enantioselectivity.