methyl (5,6-dihydro-4H-pyran-3-yl)-2-oxoacetate | 175162-42-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl (5,6-dihydro-4H-pyran-3-yl)-2-oxoacetate
• 英文别名: methyl 2-(3,4-dihydro-2H-pyran-5-yl)-2-oxoacetate
• CAS: 175162-42-2
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: BKKSOPAGOMIIKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (5,6-dihydro-4H-pyran-3-yl)-2-oxoacetate 在 lithium aluminium tetrahydride 、 四氯化锡 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Regiocontrolled fluorination of 2-hydroxyalkyl dihydropyrans and carbonyl derivatives

  摘要：

  Reaction of polysubstituted 2-hydroxyalkyldihydropyrans with DAST led regiospecifically to fluorination at the exocyclic position, except for primary alcohols. Difluorination of carbonylated analogues with deoxo-fluor(TM) occurred also regioselectively. The unexpected stability and synthetic potential of these new allylic fluorides are discussed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01601-0
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 甲醇 、 草酰氯 在 三乙胺 作用下， 以47%的产率得到methyl (5,6-dihydro-4H-pyran-3-yl)-2-oxoacetate
  参考文献：
  名称：

  3,4-二氢-2H-吡喃与草酰氯的反应：意外的双环产物的形成和晶体结构分析

  摘要：

  3,4-二氢-2-H-吡喃和草酰氯根据条件与酮酸酯，吡喃-3-羧酸或其衍生物反应，或与迄今未知的含有环己基的双环缩醛反应。氯乙烯部分。通过单晶X射线结构分析已明确阐明了后一种产物的结构。提出了其形成机制。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.456

文献信息

• Synthesis of Penta-2,4-dienenitriles by the Horner–Wadsworth–Emmons Olefination of Enones
  作者：Carlos Bencke、Mário Marangoni、Adriano Camargo、Cassio Fantinel、Helio Bonacorso、Marcos Martins、Nilo Zanatta

  DOI：10.1055/s-0036-1590871

  日期：2017.12

  Abstract Three new series of compounds, 5-alkoxy-3-(trifluoromethyl)penta-2,4-dienenitriles, 5-(phenylthio)-3-(trifluoromethyl)penta-2,4-dienenitriles, and ethyl 4-alkoxy-2-(cyanomethylene)but-3-enoates, obtained from the olefination reaction of the respective enones with diethyl cyanomethylphosphonate via the Horner–Wadsworth–Emmons olefination are reported. All products were obtained as single regioisomers;

  摘要 三个新系列化合物：5-烷氧基-3-（三氟甲基）戊-2,4-二烯腈，5-（苯硫基）-3-（三氟甲基）戊-2,4-二烯腈和乙基4-烷氧基-2-据报导，通过霍纳-沃兹沃思-埃蒙斯烯化反应，由相应的烯类与氰甲基膦酸二乙酯的烯化反应制得的（氰基亚甲基）丁-3-烯酸酯。所有产品均以单一区域异构体形式获得；但是，立体异构体的组成根据烯酮取代基而变化。基于1 H和13 C NMR化学位移，1 H– 19 F和13 C– 19 F NMR偶联常数，1的研究进行1 H NMR信号积分以及HSQC，HMBC和NOESY实验，以便确定获得的每种立体异构体的结构和百分数。 三个新系列化合物：5-烷氧基-3-（三氟甲基）戊-2,4-二烯腈，5-（苯硫基）-3-（三氟甲基）戊-2,4-二烯腈和乙基4-烷氧基-2-据报导，通过霍纳-沃兹沃思-埃蒙斯烯化反应，由相应的烯类与氰甲基膦酸二乙酯的烯化反应制得的（氰基亚甲基
• N-Vinyl-2-Oxazolidinone: New Preparation Methods and First Uses as a Dienophile
  作者：Catherine Gaulon、Patricia Gizecki、Robert Dhal、Gilles Dujardin

  DOI：10.1055/s-2002-31909

  日期：——

  N-Vinyloxazolidinone was conveniently prepared in 73% overall yield by an easy two-step procedure based on the dehydroalkoxylation of an intermediate hemiaminal using trimethylsilyl trifluoromethanesulfonate and triethylamine. The good dienophilicity of this enecarbamate was demonstrated in several [4+2] stereocontrolled processes involving activated 1-oxabutadienes under appropriate Lewis-acid catalyzed conditions. In addition, an unexpected amido-alkylation of the title compound is described under mild conditions.

  基于使用三氟甲磺酸三甲基甲硅烷基酯和三乙胺对中间体半缩醛胺进行脱氢烷氧基化，通过简单的两步程序方便地制备了 N-乙烯基恶唑烷酮，总产率为 73%。这种烯氨基甲酸酯的良好亲二烯性在适当的路易斯酸催化条件下涉及活化1-氧杂丁二烯的​​几个[4+2]立体控制过程中得到了证明。此外，描述了标题化合物在温和条件下发生意想不到的酰胺基烷基化。
• The reaction of 3,4-dihydro-2H-pyran with oxalyl chloride: Formation and crystal structure analysis of an unexpected bicyclic product
  作者：Bernd Schmidt、Frank Werner、Alexandra Kelling、Uwe Schilde

  DOI：10.1002/jhet.456

  日期：——

  3,4-Dihydro-2-H-pyran and oxalyl chloride react, depending on the conditions, to keto esters, a pyran-3-carboxylic acid or derivatives thereof, or to an hitherto unknown bicyclic acetal containing a vinyl chloride moiety. The structure of the latter product has been unambiguously elucidated by single-crystal X-ray structure analysis. A mechanism for its formation is proposed. J. Heterocyclic Chem.

  3,4-二氢-2-H-吡喃和草酰氯根据条件与酮酸酯，吡喃-3-羧酸或其衍生物反应，或与迄今未知的含有环己基的双环缩醛反应。氯乙烯部分。通过单晶X射线结构分析已明确阐明了后一种产物的结构。提出了其形成机制。J.杂环化​​学。（2010）。
• Regiocontrolled fluorination of 2-hydroxyalkyl dihydropyrans and carbonyl derivatives
  作者：Nguyen Quang Vu、Danielle Grée、René Grée、Eric Brown、Gilles Dujardin

  DOI：10.1016/s0040-4039(03)01601-0

  日期：2003.8

  Reaction of polysubstituted 2-hydroxyalkyldihydropyrans with DAST led regiospecifically to fluorination at the exocyclic position, except for primary alcohols. Difluorination of carbonylated analogues with deoxo-fluor(TM) occurred also regioselectively. The unexpected stability and synthetic potential of these new allylic fluorides are discussed. (C) 2003 Elsevier Ltd. All rights reserved.