甲基(2S)-4-甲基-3,6-二氢-2H-吡喃-2-羧酸酯 | 241126-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 甲基(2S)-4-甲基-3,6-二氢-2H-吡喃-2-羧酸酯
• 英文名称: (S)-3,6-dihydro-4-methyl-2H-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (2S)-4-methyl-3,6-dihydro-2H-pyran-2-carboxylate
• CAS: 241126-55-6
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: QRVWCQUZQVIMFD-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲基(2S)-4-甲基-3,6-二氢-2H-吡喃-2-羧酸酯 在 铂 氢气 、 二异丁基氢化铝 作用下， 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：

  3,6-dihydro-4-methyl-2H-pyran-2-carboxylic acid 在 氯化亚砜 、 硫酸 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 甲基(2S)-4-甲基-3,6-二氢-2H-吡喃-2-羧酸酯
  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

• Periselective and enantioselective carbonyl–ene reaction of isoprene with fluoroalkyl glyoxylate catalysed by modified binaphthol–titanium complex: asymmetric catalytic synthesis of enantiomerically pure ipsdienol
  作者：Masahiro Terada、Koichi Mikami

  DOI：10.1039/c39950002391

  日期：——

  The asymmetric reaction of trifluoroethyl glyoxylate 3d with isoprene 4 catalysed by the modified binaphthol–titanium complex 2b provides the ene product 5d in high periselectivity (92%) and complete enantioselectivity, which can be converted to ipsdienol 1, a component of the aggregation pheromone of the bark beetle, genus lps, in enantiomerically pure form.

  三氟乙基乙醇酸酯3d与异戊二烯4在改性联萘酚钛络合物2b催化下发生的不对称反应，以92%的高产率和完全的立体选择性提供了ene产物5d，该产物可以转化为纯对映体形式的ipsdienol 1，即树皮甲虫（lps属）聚集信息素的一个组分。
• A highly chemo- and enantio-selective hetero-Diels–Alder reaction catalysed by chiral aluminium complexes
  作者：Anette Graven、Mogens Johannsen、Karl Anker Jørgensen

  DOI：10.1039/cc9960002373

  日期：——

  A new, highly chemo- and enantio-selective catalytic hetero Diels-Alder reaction of conjugated dienes containing allylic C-H bonds with carbonyl compounds has been developed; with the use of (S)-(-)-BINOL-AlMe (BINOL = 1,1'-bi-2-naphthol) as a catalyst, simple conjugated dienes react with glyoxylate esters, giving the (R)-enantiomer of the hetero-Diels-Alder adduct as the major product with up to 97% ee.