6-acetyloxy-6-[(acetyloxy)methyl]-2H-pyran-3(6H)-one | 847056-76-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-acetyloxy-6-[(acetyloxy)methyl]-2H-pyran-3(6H)-one
• 英文别名: 6-acetoxy-6-acetoxymethyl-2H-pyran-3(6H)-one；(2-Acetyloxy-5-oxopyran-2-yl)methyl acetate
• CAS: 847056-76-2
• 化学式: C₁₀H₁₂O₆
• 分子量: 228.202
• InChiKey: HVHBNPSGPIGUKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-acetyloxy-6-[(acetyloxy)methyl]-2H-pyran-3(6H)-one 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以39 mg的产率得到(1α,2α,6α,7α)-4,7-di(acetoxy)methyl-3,11-dioxa-tricyclo[5.3.1.1^2,6]dodeca-4,8-diene-10,12-dione
  参考文献：
  名称：

  Synthesis of the 5-hydroxymethyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural products descurainin and cartorimine

  摘要：

  Reaction of pyranulose 6 with styrenes 12c or 13 and Et3N in CH2O2 at 25 degrees C afforded the [5+2] cycloadducts 14c and 15, which were hydrolyzed to give the natural products I and descurainin (2) in 24 and 27% overall yield, respectively. Heating pyranulose 6 with cinnamate ester 21 in the presence of 2,6-di-t-butylpyridine in CH3CN at 175 degrees C afforded the [5+2] cycloadduct, which was hydrolyzed to give cartorimine (3) in 13% yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.10.083
• 作为产物：
  描述：

  5-乙酰氧基甲基-2-呋喃醛 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 6-acetyloxy-6-[(acetyloxy)methyl]-2H-pyran-3(6H)-one
  参考文献：
  名称：

  Synthesis of (±)-cartorimine

  摘要：

  Heating pyranulose 4 and cinnamate 2 in the presence of 2,6-di-t-butylpyridine in CH3CN afforded the [5 divided by 2] cycloadduct, which was hydrolyzed to give 13% of cartorimine (1). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.12.007

文献信息

• Diastereoselective 1,3-dipolar cycloaddition of pyrylium ylides with chiral enamides
  作者：Kirill Tchabanenko、Colleen Sloan、Yves-Mael Bunetel、Philip Mullen

  DOI：10.1039/c2ob07007c

  日期：——

  Chiral enamides 5f–i were found to react with pyrylium ylides to give cycloadducts 6d–i in good yields with an excellent level of stereoselectivity. The chiral auxiliary was successfully removed on hydrogenolysis of compound 6f in continuous flow (H-Cube) resulting in the first asymmetric synthesis of complex amine 8.

  发现手性烯酰胺5f–i与吡啶阳离子反应，生成了立体选择性极高的环加成物6d–i，并且产率良好。在连续流动（H-Cube）条件下对化合物6f进行氢解，成功去除了手性辅助基，首次实现复杂胺8的非对称合成。
• Efficient generation of an oxidopyrylium ylide using a Pd catalyst and its [5+2] cycloadditions with several dipolarophiles
  作者：Hiroyuki Suga、Taichi Iwai、Masahiro Shimizu、Kie Takahashi、Yasunori Toda

  DOI：10.1039/c7cc09552j

  日期：——

  6-acetoxy-6-acetoxymethyl-2H-pyran-3(6H)-one using a Pd catalyst and [5+2] cycloadditions of the resulting ylide are described. Among substituted styrene derivatives as dipolarophiles, electron-rich styrenes showed higher yield (up to 80%). The [5+2] cycloaddition reactions can also be applied to exo-methylene cyclic compounds, and an improved method for the synthesis of polygalolide intermediate has been

  描述了使用Pd催化剂从6-乙酰氧基-6-乙酰氧基甲基-2 H-吡喃-3（6 H）-1生成氧化吡啶鎓叶立德的有效方法，以及所得的叶立德的[5 + 2]环加成。在取代的苯乙烯衍生物（如双极性亲和剂）中，富电子苯乙烯显示出更高的收率（高达80％）。[5 + 2]环加成反应也可以用于外亚甲基环状化合物，并且已经证明了一种改进的合成聚没食子酸酯中间体的方法。
• A Short, Formal, Biomimetic Synthesis of (±)-Polygalolides A and B
  作者：Barry B. Snider、Xiaoxing Wu、Seiichi Nakamura、Shunichi Hashimoto

  DOI：10.1021/ol0630898

  日期：2007.3.1

  Cs2CO3 resulted in hydrolysis of the lactone and acetate and conjugate addition of the hydroxyethyl group to the enone. Lactonization on acidification afforded 4 (57%), completing a two-step, formal synthesis of polygalolides A and B.

  [反应：见正文]双乙酰氧基吡喃酮9与Et3N的反应生成3-氧化吡啶鎓叶立德10，将其与α-亚甲基丁内酯进行立体和区域特异性[5 + 2]环加成反应，得到16（34％）。用Cs 2 CO 3处理16导致内酯和乙酸酯的水解以及羟乙基向烯酮的共轭加成。酸化后进行Lactonization，得到4（57％），完成了两步的聚没食子内酯A和B的正式合成。
• Triethylamine Enables Catalytic Generation of Oxidopyrylium Ylides for [5+2] Cycloadditions with Alkenes: An Efficient Entry to 8-Oxabicyclo[3.2.1]octane Frameworks
  作者：Yasunori Toda、Masahiro Shimizu、Taichi Iwai、Hiroyuki Suga

  DOI：10.1002/adsc.201800290

  日期：2018.6.15

  of 8‐oxabicyclo[3.2.1]octane derivatives including synthetic intermediates of natural products is described, in which triethylamine effectively catalyzes [5+2] cycloaddition reactions between oxidopyrylium ylides and alkenes. This method can be applied not only to intermolecular cycloadditions with various alkenes but also to intramolecular cycloadditions. The key finding is that the combined use of

  描述了一种制备包括天然产物合成中间体在内的一系列8-氧杂双环[3.2.1]辛烷衍生物的有效方法，其中三乙胺有效地催化了氧化吡啶鎓内酯与烯烃之间的[5 + 2]环加成反应。该方法不仅可以应用于具有各种烯烃的分子间环加成，而且可以应用于分子内环加成。关键发现是将具有适当碱性的有机碱与带有合适离去基团的氧化吡啶鎓前体组合使用可促进碱式氧化吡啶鎓的催化生成。
• The Stereoselective Dimerization Reaction of Oxidopyrylium Ions
  作者：Hee-Yoon Lee、Hyoun Kim、Byung Kim、Jung Kee

  DOI：10.1055/s-2007-983770

  日期：2007.7

  The dimerization reaction of oxidopyrylium ions produces doubly bridged eight-membered carbocyclic rings stereoselectively according to the substitution pattern around the pyrylium ring.

  氧化吡喃离子的二聚反应根据吡喃环周围的取代模式立体选择性地产生双桥八元碳环。