(3-ethyl-4-methyl-7-coumaryloxy)methylacetylene | 67268-46-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (3-ethyl-4-methyl-7-coumaryloxy)methylacetylene
• 英文别名: (3-ethyl-4-methyl-7-propargyloxy)coumarin；2H-1-Benzopyran-2-one, 3-ethyl-4-methyl-7-(2-propynyloxy)-；3-ethyl-4-methyl-7-prop-2-ynoxychromen-2-one
• CAS: 67268-46-6
• 化学式: C₁₅H₁₄O₃
• 分子量: 242.274
• InChiKey: KMDWNGANCAMQIP-UHFFFAOYSA-N

物化性质

• 沸点：
  403.2±45.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (3-ethyl-4-methyl-7-coumaryloxy)methylacetylene 、 3'-叠氮基-3'-脱氧-5-甲基尿苷 在 copper(l) iodide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 15.0h， 以79%的产率得到3'-deoxy-3'-[4-(3-ethyl-4-methylcoumarin-7-yloxymethylene)-1,2,3-triazol-1-yl]-5-methyluridine
  参考文献：
  名称：

  Chemoenzymatic Synthesis of 3′-Deoxy-3′-(4-Substituted-Triazol-1-YL)-5-Methyluridine

  摘要：

  An efficient protocol has been developed for the synthesis of a small library of 3-deoxy-3-(4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction of 3-azido-3-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%-92%. Here, the azido precursor compound, i.e., 3-azido-3-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K(2)CO(3)in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, H-1-, C-13 NMR spectra, and high-resolution mass spectra) data analysis.

  DOI：

  10.1080/15257770.2013.847957
• 作为产物：
  描述：

  3-乙基-7-羟基-4-甲基-2H-色烯-2-酮 、 3-溴丙炔 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以89%的产率得到(3-ethyl-4-methyl-7-coumaryloxy)methylacetylene
  参考文献：
  名称：

  Chemoenzymatic Synthesis of 3′-Deoxy-3′-(4-Substituted-Triazol-1-YL)-5-Methyluridine

  摘要：

  An efficient protocol has been developed for the synthesis of a small library of 3-deoxy-3-(4-substituted-triazol-1-yl)-5-methyluridine using Cu(I)-catalyzed Huisgen-Sharpless-Meldal 1,3-dipolar cycloaddition reaction of 3-azido-3-deoxy-5-methyluridine with different alkynes under optimized condition in an overall yields of 76%-92%. Here, the azido precursor compound, i.e., 3-azido-3-deoxy-5-methyluridine was chemoenzymatically synthesized from D-xylose in good yield. Some of the alkynes used in cycloaddition reaction were synthesized by the reaction of hydroxycoumarins or naphthols with propargyl bromide in acetone using K(2)CO(3)in excellent yields. All synthesized compounds were unambiguously identified on the basis of their spectral (IR, H-1-, C-13 NMR spectra, and high-resolution mass spectra) data analysis.

  DOI：

  10.1080/15257770.2013.847957

文献信息

• Ethers of 7-hydroxy-coumarin useful as medicaments
  申请人：Unicler

  公开号：US04151291A1

  公开（公告）日：1979-04-24

  The invention provides novel esters of 7-hydroxycoumarin of the formula ##STR1## in which each of R.sub.1 and R.sub.2 represents a hydrogen atom, a C.sub.1 -C.sub.4 alkyl, C.sub.2 -C.sub.4 alkenyl, carboxy, carboxylate, C.sub.2 -C.sub.5 alkoxycarbonyl or nitrophenyl group, and R.sub.3 represents a hydrogen atom or a group of the formula --CH.sub.2 --Z in which Z represents a di(C.sub.1 -C.sub.4 alkyl)amino group, or a saturated heterocyclic amino radical containing 5 to 7 ring members which may contain a further heteroatom, and their pharmaceutically acceptable acid addition salts. The compounds are useful as medicaments, in particular as analgesics.

  该发明提供了新型7-羟基香豆素的酯类化合物，其化学式为##STR1##其中R.sub.1和R.sub.2分别代表氢原子，C.sub.1 -C.sub.4烷基，C.sub.2 -C.sub.4烯基，羧基，羧酸酯，C.sub.2 -C.sub.5烷氧羰基或硝基苯基；R.sub.3代表氢原子或具有--CH.sub.2 --Z的基团，其中Z代表二(C.sub.1 -C.sub.4烷基)氨基基团，或含有5到7个环成员的饱和杂环氨基基团，其中可能含有进一步的杂原子，以及它们的药用可接受的酸盐。这些化合物可用作药物，特别是作为镇痛药。
• US4151291A
  申请人：——

  公开号：US4151291A

  公开（公告）日：1979-04-24