4,5,6-三甲基吡喃-2-酮 | 14818-31-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4,5,6-三甲基吡喃-2-酮
• 中文别名: 2H-吡喃-2-酮,4,5,6-三甲基-
• 英文名称: 4,5,6-trimethyl-2-pyrone
• 英文别名: 4,5,6-Trimethyl-2H-pyran-2-one；4,5,6-trimethylpyran-2-one
• CAS: 14818-31-6
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: MXYPQLFIKLZHGS-UHFFFAOYSA-N

物化性质

• 熔点：
  74 °C
• 沸点：
  241.8±9.0 °C(Predicted)
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5,6-三甲基吡喃-2-酮 在 ruthenium catalyst with atropoisomeric (R)-ligand tetrafluoroboric acid 、 氢气 作用下， 以 水 、 异丙醇 为溶剂， 60.0 ℃ 、6.0 MPa 条件下， 反应 5.0h， 生成 4,5,6-trimethyltetrahydro-2H-pyran-2-one 、 all-cis-(-)-3,4,5,6-tetrahydro-4,5,6-trimethyl-2H-pyran-2-one
  参考文献：
  名称：

  Asymmetric Hydrogenation of Substituted 2-Pyrones

  摘要：

  Various substituted 2-pyrones have been hydrogenated with high enantioselectivity (up to 97% ee) to the corresponding 5,6-dihydropyrones using cationic ruthenium catalysts containing the (6,6'-dimethoxybiphenyl-2,2'diyl)bis[3,5-di(tert-butyl)phenylphosphine] ligand. When substituents at position 3 are absent, 5,6-dihydropyrones are further hydrogenated to the fully saturated delta-lactones. In the case of 4,6-dimethyl-2H-pyran-2-one, the diastereoselectivity of the second hydrogenation step was determined by the chirality of the applied catalyst, while for the 4,5,6-trimethyl-2H-pyran-2-one a double asymmetric induction effect was observed. Other cyclic substrates with endo- or exocyclic double bonds were hydrogenated, although with substantially lower enantioselectivity with respect to the 2-pyrones.

  DOI：

  10.1021/jo982215l
• 作为产物：
  描述：

  3-甲基-3-戊烯-2-酮 在 过氧化氢苯甲酰 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 sodium ethanolate 、 三乙胺 、 乙酰氯 作用下， 以 乙醇 、 水 为溶剂， 反应 76.0h， 生成 4,5,6-三甲基吡喃-2-酮
  参考文献：
  名称：

  Photoisomerization of 4-hydroxypyrylium cations in concentrated sulfuric acid

  摘要：

  DOI：

  10.1021/jo00197a040

文献信息

• Asymmetric Hydrogenation of Substituted 2-Pyrones
  作者：Matthias J. Fehr、Giambattista Consiglio、Michelangelo Scalone、Rudolf Schmid

  DOI：10.1021/jo982215l

  日期：1999.8.1

  Various substituted 2-pyrones have been hydrogenated with high enantioselectivity (up to 97% ee) to the corresponding 5,6-dihydropyrones using cationic ruthenium catalysts containing the (6,6'-dimethoxybiphenyl-2,2'diyl)bis[3,5-di(tert-butyl)phenylphosphine] ligand. When substituents at position 3 are absent, 5,6-dihydropyrones are further hydrogenated to the fully saturated delta-lactones. In the case of 4,6-dimethyl-2H-pyran-2-one, the diastereoselectivity of the second hydrogenation step was determined by the chirality of the applied catalyst, while for the 4,5,6-trimethyl-2H-pyran-2-one a double asymmetric induction effect was observed. Other cyclic substrates with endo- or exocyclic double bonds were hydrogenated, although with substantially lower enantioselectivity with respect to the 2-pyrones.
• Photochemistry of 4-hydroxypyrylium cations in aqueous sulfuric acid
  作者：James W. Pavlik、Alfred P. Spada、Thomas E. Snead

  DOI：10.1021/jo00217a005

  日期：1985.8
• PAVLIK, J. W.;PATTEN, A. D.;BOLIN, D. R.;BRADFORD, K. C.;CLENNAN, E. L., J. ORG. CHEM., 1984, 49, N 23, 4523-4531
  作者：PAVLIK, J. W.、PATTEN, A. D.、BOLIN, D. R.、BRADFORD, K. C.、CLENNAN, E. L.

  DOI：——

  日期：——
• Substituted Diaza-Spiro-[5.5]-Undecane Derivaties and Their Use as Neurokinin Antagonists
  申请人：Janssens Eduard Frans

  公开号：US20070232636A1

  公开（公告）日：2007-10-04

  This invention concerns substituted diaza-spiro-[5.5]-undecane derivatives having neurokinin antagonistic activity, in particular NK 1 antagonistic activity, a combined NK 1 /NK 2 antagonistic activity, a combined NK 1 /NK 3 antagonistic activity and a combined NK 1 /NK 2 /NK 3 antagonistic activity, their preparation, compositions comprising them and their use as a medicine, in particular for the treatment and/or prophylaxis of schizophrenia, emesis, anxiety and depression, irritable bowel syndrome (IBS), circadian rhythm disturbances, pre-eclampsia, nociception, pain, in particular visceral and neuropathic pain, pancreatitis, neurogenic inflammation, asthma, COPD and micturition disorders such as urinary incontinence. The compounds according to the invention can be represented by general Formula (I) and comprises also the pharmaceutically acceptable acid or base addition salts thereof, the stereochemically isomeric forms thereof, the N-oxide form thereof and prodrugs thereof, wherein all substituents are defined as in Claim 1.
• US7544694B2
  申请人：——

  公开号：US7544694B2

  公开（公告）日：2009-06-09