3-Methyl-5-oxo-hexen-(2)-saeure-(1)-methylester | 14619-67-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-Methyl-5-oxo-hexen-(2)-saeure-(1)-methylester
• 英文别名: Methyl 3-methyl-5-oxohex-2-enoate
• CAS: 14619-67-1
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: YIECAKXZUGXAPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-5-oxo-hexen-(2)-saeure-(1)-methylester 在 吡啶 、 tetraphosphorus decasulfide 、 硫酸 、 盐酸羟胺 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 16.5h， 生成 甲吡司
  参考文献：
  名称：

  Development of Novel N-hydroxypyridone Derivatives as Potential Anti-Ischemic Stroke Agents

  摘要：

  Our previous study had identified ciclopirox (CPX) as a promising lead compound for treatment of ischemic stroke. To find better neuroprotective agents, a series of N-hydroxypyridone derivatives based on CPX were designed, synthesized, and evaluated in this study. Among these derivatives, compound 11 exhibits significant neuroprotection against oxygen glucose deprivation and oxidative stress -induced injuries in neuronal cells. Moreover, compound 11 possesses good blood-brain barrier permeability and superior antioxidant capability. In addition, a complex of compound 11 with olamine-11.01a possesses good water solubility, negligible hERG inhibition, and superior metabolic stability. The in vivo experiment demonstrates that 11.01a significantly reduces brain infarction and alleviates neurological deficits in middle cerebral artery occlusion rats. Hence, compound 11.01a is identified in our research as a prospective prototype in the innovation of stroke treatment.

  DOI：

  10.1021/acs.jmedchem.9b01338
• 作为产物：
  描述：

  3,3-二甲基丙烯酸 在 三氯化铝 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 生成 3-Methyl-5-oxo-hexen-(2)-saeure-(1)-methylester
  参考文献：
  名称：

  Antifungal Activity of 4-Methyl-6-alkyl-2H-pyran-2-ones

  摘要：

  A number of 4-methyl-6-alkyl-alpha-pyrones were synthesized and characterized on the basis of H-1 NMR and mass spectroscopy. These compounds were tested in vitro against pathogenic fungi, namely, Sclerotium rolfsii Saccardo, Rhizoctonia bataticola (Taub.) Butler, Pythium aphanidermatum (Edson) Fitz., Macrophomina phaseolina (Tassi), Pythium debaryanum (Hesse), and Rhizoctonia solani Nees. Lower homologues were less effective, whereas compounds such as 4-methyl-6-butyl-alpha-pyrone, 4-methyl-6-pentyl-alpha-pyrone, 4-methyl-6-hexyl-alpha-pyrone, and 4-methyl-6-heptyl-alpha-pyrone were found effective against all of the test fungi. They inhibited mycelial growth by approximately 50% (ED50) at 15-50 mu g/mL. 4-Methyl-6-hexyl-alpha-pyrone, which was found most effective, was tested against S. rolfsii in a greenhouse at 1, 5, and 10% concentrations. The 10% aqueous emulsion of 4-methyl-6-hexyl-alpha-pyrone suppressed disease development in tomato by 90-93% as compared with the untreated infested soil in the greenhouse after 35 days of treatment.

  DOI：

  10.1021/jf052792s

文献信息

• Stereochemistry and reactivity of F- and H-vinyldiazocarbonyl compounds and their phosphazines: synthesis of pyrazoles and pyridazines
  作者：Murat B. Supurgibekov、Valerija M. Zakharova、Jochim Sieler、Valerij A. Nikolaev

  DOI：10.1016/j.tetlet.2010.11.073

  日期：2011.1

  tituted (F) 2-vinyl-2-diazocarbonyl compounds, having cis-relationship of functional groups (AlkO2C, CN2), do not undergo 1,5-electrocyclization, but readily take part in the tandem Staudinger–diaza-Wittig reactions to produce trifluoromethyl-substituted pyridazines, whereas their non-fluorinated analogs (H), with trans-configuration, easily cyclize to pyrazoles, but remain intact under Staudinger–diaza-Wittig

  具有官能团（AlkO 2 C，CN 2）的顺式关系的3-（三氟甲基）取代的（F）2-乙烯基-2-重氮羰基化合物不进行1,5-电环化，但容易参与串联Staudinger-diaza-Wittig反应生成三氟甲基取代的哒嗪，而它们的非氟化类似物（H）具有反式构型，很容易环化成吡唑，但在Staudinger-diaza-Wittig反应条件下保持完整。H-和F反应性的差异-乙烯基重氮酮，乙烯基重氮乙酸酯和衍生的膦嗪显然是由AlkO 2 C和CN 2基团的不同立体化学排列引起的。
• Two-Stage Synthesis of 3-(Perfluoroalkyl)-Substituted Vinyldiazocarbonyl Compounds and Their Nonfluorinated Counterparts: A Comparative Study
  作者：G. Prakash、Valerij Nikolaev、Murat Supurgibekov

  DOI：10.1055/s-0032-1318309

  日期：——

  Two approaches for the synthesis of fluorinated (F) and nonfluorinated (H) 4-(alkoxycarbonyl)-substituted cis- and trans-vinyldiazocarbonyl compounds with substituents of variable stereoelectronic nature (H, Me, Ph, CF3, OTBS) at the C-3 atom of the vinyl double bond from the relevant 1,3-dicarbonyl compounds were compared: a pathway using the Wittig reaction followed by a diazo transfer reaction was most efficient for the synthesis of the H-vinyldiazocarbonyl compounds (total yields of up to 60%), while the yields of their F-analogues under similar conditions did not exceed 16-37%. An approach via diazo transfer followed by the Wittig reaction, in contrast, is more effective for the preparation of F-vinyldiazocarbonyl compounds (total yields 37-69%). The configuration of the resulting F-and H-vinyldiazocarbonyl compounds is evidently controlled by the steric bulk of the substituent at the C-3 atom of the vinyl double bond and, in addition, depends on the specific synthetic pathway.