ethyl α-(2,5-dimethoxybenzylidene)acetoacetate | 72676-82-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl α-(2,5-dimethoxybenzylidene)acetoacetate
• 英文别名: ethyl (2Z)-2-[(2,5-dimethoxyphenyl)methylidene]-3-oxobutanoate
• CAS: 72676-82-5
• 化学式: C₁₅H₁₈O₅
• 分子量: 278.305
• InChiKey: IJIIJVGCFSAMRP-LCYFTJDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl α-(2,5-dimethoxybenzylidene)acetoacetate 在 palladium on activated charcoal 氢氧化钾 、 N,N-dimethylformamide, thionyl chloride 、 氢气 作用下， 以 二苯醚 、 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 195.0~230.0 ℃ 、275.79 kPa 条件下， 反应 42.5h， 生成 吡曲克辛
  参考文献：
  名称：

  Synthesis and antitumor activity of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidine

  摘要：

  The synthesis of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidine (BW301U, 7) by a route that has general applicability to the preparation of many 6-(substituted benzyl)-5-methylpyrido[2,3-d]pyrimidines is described. The key intermediate, 2,4-diamino-7,8-dihydro-6-(2,5-dimethoxybenzyl)-5-methyl-7-oxopyrido[2,3-d]pyrimidine (4), is converted to the 7-chloro compound 5 by treatment with a 1:1 complex of N,N-dimethylformamide--thionyl chloride, and 5 is hydrogenolyzed with palladium on charcoal in the presence of potassium hydroxide to yield 7. BW301U is a potent lipid-soluble inhibitor of mammalian dihydrofolate reductase and has significant activity against the Walker 256 carcinosarcoma in rats.

  DOI：

  10.1021/jm00177a025
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2,5-二甲氧基苯甲醛 在 哌啶 作用下， 以 溶剂黄146 、 苯 为溶剂， 反应 3.0h， 以64%的产率得到ethyl α-(2,5-dimethoxybenzylidene)acetoacetate
  参考文献：
  名称：

  Synthesis and antitumor activity of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidine

  摘要：

  The synthesis of 2,4-diamino-6-(2,5-dimethoxybenzyl)-5-methylpyrido[2,3-d]pyrimidine (BW301U, 7) by a route that has general applicability to the preparation of many 6-(substituted benzyl)-5-methylpyrido[2,3-d]pyrimidines is described. The key intermediate, 2,4-diamino-7,8-dihydro-6-(2,5-dimethoxybenzyl)-5-methyl-7-oxopyrido[2,3-d]pyrimidine (4), is converted to the 7-chloro compound 5 by treatment with a 1:1 complex of N,N-dimethylformamide--thionyl chloride, and 5 is hydrogenolyzed with palladium on charcoal in the presence of potassium hydroxide to yield 7. BW301U is a potent lipid-soluble inhibitor of mammalian dihydrofolate reductase and has significant activity against the Walker 256 carcinosarcoma in rats.

  DOI：

  10.1021/jm00177a025

文献信息

• Treatment with dialkoxy pyridopyrimidines
  申请人：Burroughs Wellcome Co.

  公开号：US04372957A1

  公开（公告）日：1983-02-08

  Potent psoriasis activity in combination with low inhibition of histamine N-methyltransferase has been found in a class of 2,4-diamino-6-(2,5-dialkoxybenzyl)-5-methylpyrido[2,3-d]pyrimidines.

  在一类2,4-二氨基-6-(2,5-二烷氧基苯基)-5-甲基吡啶并[2,3-d]嘧啶中发现了强烈的银屑病活性，同时对组胺N-甲基转移酶的抑制作用较低。
• Medicaments for the treatment of rheumatoid arthritis
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0279565B1

  公开（公告）日：1992-01-02
• Synthesis of 3,4-Disubstituted 2,5-Dihydropyrrol-1-yloxyl Spin Label Reagents
  作者：Cecília P. Sár、József Jekö、Kálmán Hideg

  DOI：10.1055/s-1998-2177

  日期：1998.10
• J. Med. Chem. 1980, 23, 327-329
  作者：

  DOI：——

  日期：——
• US5547954A
  申请人：——

  公开号：US5547954A

  公开（公告）日：1996-08-20