5-methyl-4-oxo-5-phenyl-4,5-dihydro-furan-2-carboxylic acid pyridin-3-ylmethyl ester | 72420-44-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-methyl-4-oxo-5-phenyl-4,5-dihydro-furan-2-carboxylic acid pyridin-3-ylmethyl ester
• 英文别名: 4,5-dihydro-5-methyl-4-oxo-5-phenylfuran-2-carboxylic acid 3-pyridinylmethyl ester；Pyridin-3-ylmethyl 5-methyl-4-oxo-5-phenylfuran-2-carboxylate
• CAS: 72420-44-1
• 化学式: C₁₈H₁₅NO₄
• 分子量: 309.321
• InChiKey: SJZRKMJLDBKDPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-羟基-3-苯基丁烷-2-酮 在 吡啶 、 盐酸 、 氯化亚砜 作用下， 以 四氢呋喃 、 丙酮 、 mineral oil 、 苯 为溶剂， 生成 5-methyl-4-oxo-5-phenyl-4,5-dihydro-furan-2-carboxylic acid pyridin-3-ylmethyl ester
  参考文献：
  名称：

  Process for preparing 4,5-dihydro-4-oxofuran-2-carboxylic acid

  摘要：

  4,5-二氢-4-氧基呋喃-2-羧酸的衍生物，其特点是在位置5处有两个取代基，并且在位置3处还可以进一步以较低的烷基基团进行取代，以及相应的酯类化合物被披露。上述化合物在哺乳动物中是有用的降脂药物。还披露了制备这些化合物的新方法。

  公开号：

  US04169202A1

文献信息

• Hypolipidemic derivatives of 4,5-dihydro-4-oxofuran-2-carboxylic acid
  申请人：American Home Products Corporation

  公开号：US04244958A1

  公开（公告）日：1981-01-13

  Derivatives of 4,5-dihydro-4-oxofuran-2-carboxylic acid characterized by having two substituents at position 5 and in addition being optionally further substituted at position 3 with a lower alkyl group, as well as esters therefor are disclosed. The foregoing compounds are useful hypolipidemic agents in a mammal. Novel methods for the preparation of these compounds also are disclosed.

  4,5-二氢-4-氧基呋喃-2-羧酸的衍生物在位置5处具有两个取代基，并且还可以在位置3进一步以较低的烷基取代，以及其酯类化合物也被揭示。上述化合物在哺乳动物中是有用的降脂药物。还揭示了制备这些化合物的新方法。
• Derivatives of 4,5-dihydro-4-oxofuran-2-carboxylic acid, especially for use as hypolipidemic agents, processes for their preparation, pharmaceutical compositions comprising them, tetrahydropyran-2,3,5-triones useful in the preparation of the said derivatives and a process for preparing these tetrahydropyran-2,3,5-triones
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0006305A1

  公开（公告）日：1980-01-09

  Compounds of formula I in which R1 and R2 each is lower alkyl, cyclo(lower)alkyl, lower alkoxy(lower)alkylene, phenyl or phenyl mono- or disubstituted with lower alkyl, lower alkoxy, halo, nitro or trifluoromethyl; or RI and R2 together form a -(CH2)m-X-(CH2)n- chain wherein m and n each is an integer from one to four and X is methylene, oxa or thia; or R1 and R2 together with the carbon atom to which they are joined form a spiro-[1,2,3,4-tetrahydronaphthalene]-1 or spiro[indan]-1 radical; R3 is hydrogen or lower alkyl; and R' is hydrogen, lower alkyl, cyclo(lower)alkyl, phenyl(lower)alkylene, amino-(lower)alkylene, lower alkylamino(lower)alkylene, di(lower alkyl)amino(lower)alkylene or 3-pyridinyl(lower)alkylene, or a therapeutically acceptable addition salt thereof are disclosed which possess hypolipidemic activity, and can be used in pharmaceutical compositions. The compounds of formula I may be prepared by cyclising a corresponding compound of formula X and if desired esterifying. Tetrahydropyran-2,3,5-trione intermediates are also disclosed.

  式 I 的化合物 其中 R1 和 R2 各自为低级烷基、环（低级）烷基、低级烷氧基（低级）亚烷基、苯基或与低级烷基、低级烷氧基、卤代、硝基或三氟甲基单取代或二取代的苯基；或 RI 和 R2 共同形成-(CH2)m-X-(CH2)n-链，其中 m 和 n 均为 1 至 4 的整数，X 为亚甲基、氧杂环丁烷或硫杂环丁烷；或 R1 和 R2 与它们连接的碳原子共同形成螺-[1,2,3,4-四氢萘]-1 或螺[茚]-1 自由基；R3是氢或低级烷基；R'是氢、低级烷基、环（低级）烷基、苯基（低级）亚烷基、氨基（低级）亚烷基、低级烷基氨基（低级）亚烷基、二（低级烷基）氨基（低级）亚烷基或 3-吡啶基（低级）亚烷基，或其治疗上可接受的加成盐，这些化合物具有降血脂活性，可用于药物组合物中。 式 I 化合物可通过环化相应的式 X 化合物 并根据需要进行酯化。此外，还公开了四氢吡喃-2,3,5-三酮中间体。
• US4169202A
  申请人：——

  公开号：US4169202A

  公开（公告）日：1979-09-25
• US4244958A
  申请人：——

  公开号：US4244958A

  公开（公告）日：1981-01-13
• [EN] DERIVATIVES OF 4,5-DIHYDRO-4-OXOFURAN-2-CARBOXYLIC ACID,PREPARATIONS AND USE THEREOF AND TETRAHYDROPYRAN-2,3,5-TRIONE INTERMEDIATES
  申请人：——

  公开号：WO1980000025A1

  公开（公告）日：1980-01-10

  (EN) Compounds of formula I (FORMULA) in which R1 and R2 each is lower alkyl, cyclo (lower) alkyl, lower alkoxy (lower) alkylene, phenyl or phenyl mono- or disubstituted with lower alkyl, lower alkoxy, halo, nitro or trifluoromethyl; or R1 and R2 together form a -(CH2)m-X-(CH2)n- chain wherein m and n each is an integer from one to four and X is methylene, oxa or thia; or R1 and R2 together with the carbon atom to which they are joined form a spiro(1,2,3,4-tetrahydro napthalene)-1 or spiro(indan)-1 radical; R3 is hydrogen or lower alkyl; and R4 is hydrogen, lower alkyl, cyclo (lower) alkyl, phenyl (lower) alkylene, amino (lower) alkylene, lower alkyl-amino (lower) alkylene, di (lower alkyl) amino (lower) alkylene or 3-pyridinyl (lower) alkylene, or a therapeutically acceptable addition salt thereof are disclosed which possess hypolipidemic activity, and can be used in pharmaceutical compositions. The compounds of formula I may be prepared by cyclising a corresponding compound of formula X (FORMULA) and if desired esterifying. Tetrahydropyran-2,3,5-trione intermediates are also disclosed. (FR) Composes de formule I (FORMULE) dans laquelle R1 et R2 sont chacun un alkyle inferieur, un cycloalkyle (inferieur), un alkoxy inferieur alkylene (inferieur), un phenyle ou phenyle mono ou bisubstitue avec un alkyle inferieur, un alkoxy inferieur, un nitro ou trifluoromethyle; ou R1 et R2 forment ensemble une chaine - (CH2) m - X - (CH2) n - dans laquelle m et n sont chacun un nombre entier compris entre un et quatre et X est un methylene, oxa ou thia; ou R1 et R2 forment ensemble avec l"atome de carbone auquel ils sont rattaches un radical spiro (1,2,3,4-tetrahydronaphtalene)-1 ou un radical spiro(indan)-; R3 est l"hydrogene ou un alkyle inferieur et R4 est l"hydrogene, un alkyle inferieur, un cycloalkyle (inferieur), un phenyle, un alkylene (inferieur), un alkylene amino inferieur, un alkyle amino alkylene (inferieur), un diamino (alkyle inferieur) alkylene (inferieur) ou 3-pyridinyle alkylene (inferieur), ou un sel d"addition therapeutiquement acceptable, presentent une activite hypolipidique et peuvent etre utilises dans des compositions pharmaceutiques. Les composes de formule I peuvent etre prepares par cyclisation d"un compose correspondant de formule X (FORMULE) et, si desire, par esterification. Des substances intermediaires de tetrahydropyrane-2,3,5-trione sont egalement decrites.