3,6-dihydro-4-methyl-2H-pyran-2-carboxylic acid | 19353-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3,6-dihydro-4-methyl-2H-pyran-2-carboxylic acid
• 英文别名: 4-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid；4-methyl-3,6-dihydro-2H-pyran-2-carboxylic acid
• CAS: 19353-25-4
• 化学式: C₇H₁₀O₃
• mdl: MFCD19228487
• 分子量: 142.155
• InChiKey: RNESUVFBQQXRIC-UHFFFAOYSA-N

物化性质

• 沸点：
  275.6±40.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 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：

  3,6-dihydro-4-methyl-2H-pyran-2-carboxylic acid 在 铂 氯化亚砜 、 硫酸 、 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (+)-反式玫瑰醚
  参考文献：
  名称：

  Structure Elucidation, Enantioselective Analysis, and Biogenesis of Nerol Oxide in Pelargonium Species

  摘要：

  A novel enantioselective synthesis of nerol oxide (3,6-dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran) was used for the determination of the absolute configuration at C-2. The order of elution of the enantiomers on octakis-(2,3-di-O-butyryl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin in OV 1701-vi as the chiral stationary phase in enantioselective GC was determined as (2R) before (2S). Enantioselective multidimensional GC/MS (enantio-MDGC/MS) was used for the determination of the enantiomeric ratios of nerol oxide in different geranium oils. As a result, in all investigated oils nerol oxide occurs as a racemate. The biogenesis of nerol oxide in Pelargonium species was investigated by feeding experiments using deuterium-labeled neryl glucoside as the precursor. The Pelargonium plants were able to convert the fed precursor into racemic nerol oxide, which has to be considered as a "natural racemate"

  DOI：

  10.1021/jf981245m
• 作为产物：
  描述：

  乙醛酸 、 天然橡胶 反应 15.0h， 生成 3,6-dihydro-4-methyl-2H-pyran-2-carboxylic acid
  参考文献：
  名称：

  Structure Elucidation, Enantioselective Analysis, and Biogenesis of Nerol Oxide in Pelargonium Species

  摘要：

  A novel enantioselective synthesis of nerol oxide (3,6-dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran) was used for the determination of the absolute configuration at C-2. The order of elution of the enantiomers on octakis-(2,3-di-O-butyryl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin in OV 1701-vi as the chiral stationary phase in enantioselective GC was determined as (2R) before (2S). Enantioselective multidimensional GC/MS (enantio-MDGC/MS) was used for the determination of the enantiomeric ratios of nerol oxide in different geranium oils. As a result, in all investigated oils nerol oxide occurs as a racemate. The biogenesis of nerol oxide in Pelargonium species was investigated by feeding experiments using deuterium-labeled neryl glucoside as the precursor. The Pelargonium plants were able to convert the fed precursor into racemic nerol oxide, which has to be considered as a "natural racemate"

  DOI：

  10.1021/jf981245m

文献信息

• Merging Photoredox and Nickel Catalysis: Decarboxylative Cross-Coupling of Carboxylic Acids with Vinyl Halides
  作者：Adam Noble、Stefan J. McCarver、David W. C. MacMillan

  DOI：10.1021/ja511913h

  日期：2015.1.21

  Decarboxylative cross-coupling of alkyl carboxylic acids with vinyl halides has been accomplished through the synergistic merger of photoredox and nickel catalysis. This new methodology has been successfully applied to a variety of α-oxy and α-amino acids, as well as simple hydrocarbon-substituted acids. Diverse vinyl iodides and bromides give rise to vinylation products in high efficiency under mild

  烷基羧酸与乙烯基卤化物的脱羧交叉偶联是通过光氧化还原和镍催化的协同合并实现的。这种新方法已成功应用于各种α-氧基和α-氨基酸，以及简单的烃取代酸。不同的乙烯基碘化物和溴化物在温和、操作简单的反应条件下高效地产生乙烯基化产物。
• Enhancement of Dienophilic and Enophilic Reactivity of the Glyoxylic Acid by Bismuth(III) Triflate in the Presence of Water
  作者：H. Laurent-Robert、C. Le Roux、J. Dubac

  DOI：10.1055/s-1998-1869

  日期：1998.10

  Bismuth(III) trifluoromethanesulfonate (1) is found to efficiently catalyze carbonyl-Diels-Alder or carbonyl-ene reactions between glyoxylic acid and classical dienes or substituted olefins, in the presence of water.

  三氟甲烷磺酸铋(III)（1）在水的存在下，能够高效催化羟基乙酸与经典二烯或取代烯烃之间的羰基-达尔斯-阿尔德反应或羰基-烯反应。
• Aqueous hetero Diels-Alder reactions: The carbonyl case.
  作者：A. Lubineau、J. Augé、E. Grand、N. Lubin

  DOI：10.1016/s0040-4020(01)81759-2

  日期：1994.8

  Commercially available aqueous solution of glyoxylic acid, pyruvaldehyde and glyoxal were shown to react with cyclic or non-cyclic dienes to give the corresponding cycloadducts and/or alpha-hydroxy gamma-lactones. Activated ketone (Pyruvic acid) was shown to react as well in the same conditions.
• Structure Elucidation, Enantioselective Analysis, and Biogenesis of Nerol Oxide in <i>Pelargonium</i> Species
  作者：Matthias Wüst、Jürgen Reindl、Sabine Fuchs、Thomas Beck、Armin Mosandl

  DOI：10.1021/jf981245m

  日期：1999.8.1

  A novel enantioselective synthesis of nerol oxide (3,6-dihydro-4-methyl-2-(2-methyl-1-propenyl)-2H-pyran) was used for the determination of the absolute configuration at C-2. The order of elution of the enantiomers on octakis-(2,3-di-O-butyryl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin in OV 1701-vi as the chiral stationary phase in enantioselective GC was determined as (2R) before (2S). Enantioselective multidimensional GC/MS (enantio-MDGC/MS) was used for the determination of the enantiomeric ratios of nerol oxide in different geranium oils. As a result, in all investigated oils nerol oxide occurs as a racemate. The biogenesis of nerol oxide in Pelargonium species was investigated by feeding experiments using deuterium-labeled neryl glucoside as the precursor. The Pelargonium plants were able to convert the fed precursor into racemic nerol oxide, which has to be considered as a "natural racemate"