3-(3-hydroxy-1-propoxy)-2-methyl-4-pyrone | 139645-13-9

• 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-(3-hydroxy-1-propoxy)-2-methyl-4-pyrone
• 英文别名: 3-(3-hydroxypropoxy)-2-methyl-4H-pyran-4-one；3-(3-hydroxypropoxy)-2-methylpyran-4-one
• CAS: 139645-13-9
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: IEPGPSMYRSFOSV-UHFFFAOYSA-N

物化性质

• 沸点：
  390.3±42.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-hydroxy-1-propoxy)-2-methyl-4-pyrone 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以46%的产率得到3-(2-Methyl-4-oxo-4H-pyran-3-yloxy)-propionic acid
  参考文献：
  名称：

  Study of hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydro-pyridin-3-yloxyethanoic acid and 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid by 1H NMR spectroscopy and X-ray crystallography

  摘要：

  A series of 1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acids and 3-(1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acids have been synthesized via the corresponding pyran-4-ones. Ring proton chemical shifts indicate hydrogen bonding between the side-chain carboxylic acid proton and the 4-oxo group of the heterocycle to be present only for the pyridinone species in DMSO solution. X-Ray crystallography demonstrates the hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acid to be very strong (O-O = 2.441 angstrom) and intramolecular, giving a unique 8-membered chelate ring. The analogous hydrogen bonding in 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid is however strong (O-O = 2.541 angstrom) and intermolecular, giving an infinite structure.

  DOI：

  10.1039/p29930000451
• 作为产物：
  描述：

  麦芽醇 、 3-氯-1-丙醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以50%的产率得到3-(3-hydroxy-1-propoxy)-2-methyl-4-pyrone
  参考文献：
  名称：

  Study of hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydro-pyridin-3-yloxyethanoic acid and 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid by 1H NMR spectroscopy and X-ray crystallography

  摘要：

  A series of 1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acids and 3-(1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acids have been synthesized via the corresponding pyran-4-ones. Ring proton chemical shifts indicate hydrogen bonding between the side-chain carboxylic acid proton and the 4-oxo group of the heterocycle to be present only for the pyridinone species in DMSO solution. X-Ray crystallography demonstrates the hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acid to be very strong (O-O = 2.441 angstrom) and intramolecular, giving a unique 8-membered chelate ring. The analogous hydrogen bonding in 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid is however strong (O-O = 2.541 angstrom) and intermolecular, giving an infinite structure.

  DOI：

  10.1039/p29930000451

文献信息

• Dialkoxy-pyridinyl-benzimidazole derivatives, process for their
  申请人：Aktiebolaget Astra

  公开号：US05430042A1

  公开（公告）日：1995-07-04

  The novel compounds of the formula I ##STR1## and physiologically acceptable salts thereof, wherein R.sup.1 and R.sup.2, which are different is each H alkyl containing 1-4 carbon atoms or --C(O)--R.sup.5 ; wherein R.sup.5 is alkyl containing 1-4 carbon atoms or alkoxy containing 1-4 carbon atoms and one of R.sup.1, or R.sup.2 is always selected from the group --C(O)--R.sup.5 ; R.sup.3 and R.sup.4 are the same or different and selected from ##STR2## and --CH.sub.2 CH.sub.2 OCH.sub.3 or R.sup.3 and R.sup.4 together with the adjacent oxygen atoms atached to the pyridine ring and the carbon atoms in the pyridine ring form a ring, wherein the part constituted by R.sup.3 and R.sup.4 is --CH.sub.2 CH.sub.2 CH.sub.2 --, or --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --; as well as intermediates, pharmaceutical compositions containing such compounds as active ingredient and the use of the compounds in medicine.

  该式的新化合物及其生理上可接受的盐，其中R.sup.1和R.sup.2是不同的，分别是含有1-4个碳原子的H烷基或--C(O)--R.sup.5；其中R.sup.5是含有1-4个碳原子的烷基或含有1-4个碳原子的烷氧基，R.sup.1或R.sup.2中的一个始终选择自群--C(O)--R.sup.5；R.sup.3和R.sup.4相同或不同，选择自##STR2## 和--CH.sub.2 CH.sub.2 OCH.sub.3，或者R.sup.3和R.sup.4与连接到吡啶环上的相邻氧原子和吡啶环中的碳原子一起形成一个环，其中由R.sup.3和R.sup.4构成的部分为--CH.sub.2 CH.sub.2 CH.sub.2--，或--CH.sub.2--CH.sub.2--或--CH.sub.2--；以及中间体、含有这种化合物作为活性成分的药物组合物和在医学中使用这种化合物。
• DIALKOXY-PYRIDINYL-BENZIMIDAZOLE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR PHARMACEUTICAL USE
  申请人：AKTIEBOLAGET ASTRA

  公开号：EP0593463A1

  公开（公告）日：1994-04-27
• US5430042A
  申请人：——

  公开号：US5430042A

  公开（公告）日：1995-07-04
• [EN] DIALKOXY-PYRIDINYL-BENZIMIDAZOLE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR PHARMACEUTICAL USE
  申请人：——

  公开号：WO1991019712A1

  公开（公告）日：1991-12-26

  [EN] The novel compounds of formula (I) and physiologically acceptable salts thereof, wherein R<1> and R<2>, which are different, is each H, alkyl containing 1-4 carbon atoms or -C(O)-R<5>; wherein R<5> is alkyl containing 1-4 carbon atoms or alkoxy containing 1-4 carbon atoms and one of R<1>, or R<2> is always selected from the group -C(O)-R<5>; R<3> and R<4> are the same or different and selected from -CH3, -C2H5, (a), (b), and -CH2CH2OCH3 or R<3> and R<4> together with the adjacent oxygen atoms attached to the pyridine ring and the carbon atoms in the pyridine ring form a ring, wherein the part constituted by R<3> and R<4> is -CH2CH2CH2-, or -CH2-CH2- or -CH2-; as well as intermediates, pharmaceutical compositions containing such compounds as active ingredient and use of the compounds in medicine.
  [FR] On décrit de nouveaux composés de formule (I) et des sels physiologiquement acceptables de ceux-ci, où R1 et R2, qui sont différents, représentent chacun H, un alkyle contenant de 1 à 4 atomes de carbone ou -C(O)-R5; où R5 représente un alkyle contenant de 1 à 4 atomes de carbone ou un alcoxy contenant de 1 à 4 atomes de carbone et soit R1 soit R2 est toujours choisi à partir du groupe -C(O)-R5; R3 et R4 sont les mêmes ou différents et choisis à partir de -CH3, -C2H5, (a), (b), et -CH2CH2OCH3, ou R3 et R4 forment un cycle avec les atomes d'oxygène contigus rattachés au cycle pyridique et les atomes de carbone dans le cycle pyridique, où la partie composée de R3 et R4 représente -CH2CH2CH2-, ou -CH2-CH2- ou -CH2-. On décrit aussi des éléments intermédiaires, des compositions pharmaceutiques contenant de tels composés comme ingrédient actif et l'utilisation de ces composés dans le domaine médical.
• Study of hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydro-pyridin-3-yloxyethanoic acid and 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid by 1H NMR spectroscopy and X-ray crystallography
  作者：Paul S. Dobbin、Robert C. Hider、Safia K. Rizvi、Kim L. Maki、Dick van der Helm

  DOI：10.1039/p29930000451

  日期：——

  A series of 1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acids and 3-(1,2-dialkyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acids have been synthesized via the corresponding pyran-4-ones. Ring proton chemical shifts indicate hydrogen bonding between the side-chain carboxylic acid proton and the 4-oxo group of the heterocycle to be present only for the pyridinone species in DMSO solution. X-Ray crystallography demonstrates the hydrogen bonding in 1-ethyl-2-methyl-4-oxo-1,4-dihydropyridin-3-yloxyethanoic acid to be very strong (O-O = 2.441 angstrom) and intramolecular, giving a unique 8-membered chelate ring. The analogous hydrogen bonding in 3-(1,2-diethyl-4-oxo-1,4-dihydropyridin-3-yloxy)propanoic acid is however strong (O-O = 2.541 angstrom) and intermolecular, giving an infinite structure.