2,4-dimethyl-5H-chromeno[3,4-c]pyridin-5-one | 104431-78-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,4-dimethyl-5H-chromeno[3,4-c]pyridin-5-one
• 英文别名: 2,4-dimethyl-chromeno[3,4-c]pyridin-5-one；2,4-Dimethyl-chromeno[3,4-c]pyridin-5-on；2,4-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one；2,4-Dimethyl-chromeno[3,4-c]pyridin-5-one；2,4-dimethylchromeno[3,4-c]pyridin-5-one
• CAS: 104431-78-9
• 化学式: C₁₄H₁₁NO₂
• 分子量: 225.247
• InChiKey: MLWSBGKBZWKDEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,4-dimethyl-5H-chromeno[3,4-c]pyridin-5-one 在 硝酸 作用下， 生成 2,4-dimethyl-9-nitro-chromeno[3,4-c]pyridin-5-one
  参考文献：
  名称：

  69.杂环化合物的新合成。第十五部分。9：10-二氢-10-酮-1：3-二甲基-2-氮杂-9-氧杂菲

  摘要：

  DOI：

  10.1039/jr9520000334
• 作为产物：
  描述：

  dimethyl 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.83h， 生成 2,4-dimethyl-5H-chromeno[3,4-c]pyridin-5-one
  参考文献：
  名称：

  A novel, nonsteroidal inhibitor of androgen binding to the rat androgen binding protein: diethyl [[[3-(2,6-dimethyl-4-pyridinyl)-4-fluorophenyl]amino]methylene]propanedioate

  摘要：

  In vitro binding studies demonstrate the binding specificity of a series of 4-aryl-2,6-dimethylpyridines for the rat epididymal androgen binding protein (rABP). The compounds bound competitively to rABP but have very weak or no demonstrable affinity for rat ventral prostate androgen receptor and human sex hormone binding globulin. In particular, compound 11, diethyl [[[3-(2,6-dimethyl-4-pyridinyl)-4-fluorphenyl]amino]methylene] propanedioate, bound with high affinity to rABP (binding affinity about 1/3 that of the endogenous ligand 5 alpha-dihydrotestosterone). However, additional in vitro binding studies indicated that 11 did not bind to testicular or epididymal ABP from rabbit, rhesus monkey, and human. Nevertheless, the specificity and relatively high affinity of these nonsteroidal compounds make them unique and potentially ideal agents for the study of the role of ABP in spermatogenesis and sperm maturation in the rat.

  DOI：

  10.1021/jm00163a021

文献信息

• Ruthenium-Catalyzed C–H Arylation of Diverse Aryl Carboxylic Acids with Aryl and Heteroaryl Halides
  作者：Liangbin Huang、Daniel J. Weix

  DOI：10.1021/acs.orglett.6b02862

  日期：2016.10.21

  ligated to tricyclohexylphosphine or di-tert-butylbipyridine catalyzes the arylation of carboxylic acids with diverse aryl halides (iodide, bromide, and triflate; aryl and heteroaryl). In addition, arylations with 2-iodophenol formed benzochromenones, carboxylate was shown to be a stronger donor than an amide, and the arylation of a pyridine carboxylate was demonstrated. Stoichiometric studies demonstrated

  与三环己基膦或二叔丁基联吡啶连接的钌催化羧酸与各种芳基卤化物（碘化物，溴化物和三氟甲磺酸盐；芳基和杂芳基）的芳基化反应。此外，与2-碘苯酚的芳基化反应形成苯并铬酮，表明羧酸盐是比酰胺更强的供体，并且证明了吡啶羧酸盐的芳基化。化学计量学研究表明，添加的配体是与亲电子试剂反应所必需的，而不是C–H键。
• Preparation of intermediates to
  申请人：Sterling Drug Inc.

  公开号：US04699984A1

  公开（公告）日：1987-10-13

  Shown is the process which comprises heating 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid to produce a mixture of 4-(2-fluorophenyl)-2,6-dimethylpyridine and 2,4-dimethyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one, separating the components of said mixture and nitrating 4-(2-fluorophenyl)-2,6-dimethylpyridine to produce 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine. Also shown are the 3-step synthesis of 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid from 2-fluorobenzaldehyde and the five step synthesis of 1-ethyl-6-fluoro-1,4-dihydro-7-(2,6-dimethyl-4-pyridinyl)-4-oxo-3-quinolin ecarboxylic acid, a highly potent antibacterial agent, starting with 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine. Other intermediates shown in said five step synthesis include 3-(2,6-dimethyl-4-pyridinyl)-4-fluorobenzeneamine and diethyl 4-fluoro-3-(2,6-dimethyl-4-pyridinyl)anilinomethylenemalonate.

  该过程包括加热4-(2-氟苯基)-2,6-二甲基-3,5-吡啶二甲酸，产生4-(2-氟苯基)-2,6-二甲基吡啶和2,4-二甲基-5H-[1]苯并吡喃[3,4-c]吡啶-5-酮的混合物，分离该混合物的组分并对4-(2-氟苯基)-2,6-二甲基吡啶进行硝化，以产生4-(2-氟-5-硝基苯基)-2,6-二甲基吡啶。还展示了从2-氟苯甲醛合成4-(2-氟苯基)-2,6-二甲基-3,5-吡啶二甲酸的三步合成和从4-(2-氟-5-硝基苯基)-2,6-二甲基吡啶开始的1-乙基-6-氟-1,4-二氢-7-(2,6-二甲基-4-吡啶基)-4-氧-3-喹啉羧酸的五步合成，该化合物是一种高效的抗菌剂。在该五步合成中展示了其他中间体，包括3-(2,6-二甲基-4-吡啶基)-4-氟苯胺和二乙酸二乙酯4-氟-3-(2,6-二甲基-4-吡啶基)苯胺甲基亚甲基丙烯酸酯。
• 7-(Pyridinyl)-/-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid having antibacterial activity and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0179239A2

  公开（公告）日：1986-04-30

  1-Ethyt-6-ftuoro-1,4-dihydro-7-(2,6-dimethy)-4-pyridinyt)-4-oxo-3-quinolinecarboxylic acid or salt thereof, a novel compound useful highly potent antibacterial agent with a broad spectrum of anti-microbial activity, is prepared by nitrating the corresponding 6-desfluoro compound to produce the corresponding 6-nitro compound, reducing the latter compound to produce the corresponding 6-amino compound and converting the 6-amino via its diazonium salt to said 6-fluoro compound. Said novel acid is also prepared via intermediates prepared by heating 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid to produce a mixture of 4-(2-fluorophenyl)-2,6-di-methylpyridine and 2,4-dimethyl-5H-[1]benzopyrano[3,4-c)pyridin-5-one, separating the components of said mixture and nitrating 4-(2-fluorophenyl)-2,6-dimethylpyridine to produce 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine.

  1-乙基-6-氟-1,4-二氢-7-(2,6-二甲基)-4-吡啶)-4-氧代-3-喹啉羧酸或其盐是一种新型化合物，是一种具有广谱抗微生物活性的高效抗菌剂、其制备方法是：硝化相应的 6-去氟化合物，生成相应的 6-硝基化合物；还原后者，生成相应的 6-氨基化合物；然后通过重氮盐将 6-氨基化合物转化为所述 6-氟化合物。所述新型酸也可以通过加热 4-(2-氟苯基)-2,6-二甲基-3,5-吡啶二羧酸生成 4-(2-氟苯基)-2,6-二甲基吡啶和 2、4-(2-氟苯基)-2,6-二甲基吡啶和 2,4-二甲基-5H-[1]苯并吡喃并[3,4-c]吡啶-5-酮的混合物，分离所述混合物的组分并硝化 4-(2-氟苯基)-2,6-二甲基吡啶，生成 4-(2-氟-5-硝基苯基)-2,6-二甲基吡啶。
• Condensations of 3-Acetocoumarin with Amides, and with Amides and Ketones¹
  作者：C. F. Koelsch、S. A. Sundet

  DOI：10.1021/ja01160a071

  日期：1950.4
• Kahn et al., Journal of the Chemical Society, 1949, p. 2128,2133
  作者：Kahn et al.

  DOI：——

  日期：——