7-hydroxy-8-propionyl-4-methylcoumarin | 3361-71-5

• 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: 7-hydroxy-8-propionyl-4-methylcoumarin
• 英文别名: 8-propionyl-7-hydroxy-4-methylcoumarin；7-hydroxy-4-methyl-8-propionyl-coumarin；7-Hydroxy-4-methyl-8-propionyl-cumarin；7-hydroxy-4-methyl-8-propionyl-2H-chromen-2-one；7-hydroxy-4-methyl-8-propanoylchromen-2-one
• CAS: 3361-71-5
• 化学式: C₁₃H₁₂O₄
• mdl: MFCD00823578
• 分子量: 232.236
• InChiKey: YTEBADYGXJZKDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  7-hydroxy-8-propionyl-4-methylcoumarin 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以65%的产率得到3-bromo-8-(2-bromopropanoyl)-7-hydroxy-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Cascaval, Alexandru; Wegner, Gerhard, Revue Roumaine de Chimie, 1992, vol. 37, # 6, p. 723 - 728

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基伞形酮基丙酸酯 在 aluminum (III) chloride 作用下， 生成 7-hydroxy-8-propionyl-4-methylcoumarin
  参考文献：
  名称：

  Synthesis of propiophenone derivatives as new class of antidiabetic agents reducing body weight in db/db mice

  摘要：

  A series of propiophenone derivatives (6-23) have been synthesized and evaluated for their in vivo anti-hyperglycemic activities in sucrose loaded model (SLM), sucrose challenged streptozotocin (STZ-S) induced diabetic rat model and C57BL/KsJ db/db diabetic mice model. Compound 15 and 16 were emerged as potent antihyperglycemics and lipid lowering agents. These compounds (15, 16) further validate the potency by reducing body weight and food intake in db/db mice model. Possible mechanism of action for the propiophenone derivatives was established by the evaluation in various in vitro models. Interestingly some of the compounds were efficiently inhibiting PTP-1B. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.027

文献信息

• Synthesis and structures of boron complexes of acyl hydroxy coumarins
  作者：A. V. Manaev、T. A. Chibisova、K. A. Lyssenko、M. Yu. Antipin、V. F. Traven’

  DOI：10.1007/s11172-006-0553-z

  日期：2006.11

  New boron chelates were synthesized by the reactions of 3-acetyl-4-hydroxycoumarin and 8-acyl-7-hydroxy-4-methylcoumarins with boron trifluoride etherate and hydroxybenzodioxaborole. The structure of 3-acetyl-4-difluoroboryloxycoumarin containing an intramolecular C=O...B coordination bond was established by X-ray diffraction.

  通过3-乙酰-4-羟基香豆素和8-酰基-7-羟基-4-甲基香豆素与三氟化硼醚合物和羟基苯并二氧杂环戊烷反应合成了新的硼螯合物。3-乙酰-4-二氟硼酰氧基香豆素的结构包含分子内C=O...B 配位键的X 射线衍射建立。
• One-pot synthesis of angular furocoumarins: A simple protocol involving unprecedented intramolecular aldol condensation
  作者：Lakshmi Narayan Dutta、Banani De、Amarendra Patra

  DOI：10.1002/jhet.5570450306

  日期：2008.5

  Refluxing of hydroxycoumarinyl ketones with methyl γ-bromocrotonate in dry acetone in presence of anhydrous K2CO3 afforded substituted angelicins (angular furanocoumarins) in satisfactory yields through intramolecular Aldol condensation followed by β-elimination.

  在无水K 2 CO 3的存在下，在干燥的丙酮中将γ-溴代巴豆酸甲酯与羟基香豆素基酮回流，通过分子内Aldol缩合，然后进行β消除，以令人满意的产率提供了取代的当归类（角呋喃香豆素）。
• Feasibility of sigmatropic rearrangement on electron-deficient coumarinyl ketones
  作者：Lakshmi Narayan Dutta、Banani De、Godhuli Pal、Amarendra Patra

  DOI：10.1139/v08-037

  日期：2008.5.1

  Different alkyl/aryl 7-hydroxy-8-coumarinyl ketones were converted to 7-O-allyl and 7-O-cyclohexenyl ethers and the study of hitherto unreported sigmatropic rearrangement on 7-O-allyl and 7-O-cyclohex-2'-ene-1'-ylcoumarinyl ketones prepared is accounted herein. The rearrangement yielded alkyl/aryl 6-allyl-7-hydroxy-8-coumarinyl ketones 3 and alkyl/aryl 6-cyclohex-2'-en-1'-yl-7-hydroxy-8-coumarinyl ketones 7 as the major products. Interestingly, unusual selectivity was observed in the case of alkyl 7-O-allylcoumarinyl ketones. Thus alkyl 3-allyl-7-hydroxy-8-coumarinyl ketones 4 and alkyl 8-allyl-7-hydroxy-6-coumarinyl ketones 5 were the outcome from alkyl 7-O-allyl-8-coumarinyl ketones and alkyl 4-methyl-7-O-allyl-8-coumarinyl ketones, respectively, albeit in minor yields.Key words: allyloxycoumarinyl ketones, 7-O-cyclohex-2'-en-1'-ylcoumarinyl ketones, sigmatropic rearrangement, 3-allylcoumarinyl ketones, 8-allylcoumarinyl ketones.

  不同的烷基/芳基 7-羟基-8-香豆素酮被转化为 7-O-烯丙基醚和 7-O-环己烯基醚，本文介绍了对所制备的 7-O-烯丙基和 7-O-环己烯-2'-烯-1'-基香豆素酮进行的迄今未报道的对称重排的研究。重排的主要产物是烷基/芳基 6-烯丙基-7-羟基-8-香豆素酮 3 和烷基/芳基 6-环己-2'-烯-1'-基-7-羟基-8-香豆素酮 7。有趣的是，在烷基 7-O-烯丙基香豆素酮中观察到了不同寻常的选择性。因此，3-烯丙基-7-羟基-8-香豆素酮烷基 4 和 8-烯丙基-7-羟基-6-香豆素酮烷基 5 分别是 7-O-烯丙基-8-香豆素酮烷基和 4-甲基-7-O-烯丙基-8-香豆素酮烷基的产物，尽管产率较低。关键词：烯丙基香豆素酮、7-O-环己-2'-烯-1'-基香豆素酮、对称重排、3-烯丙基香豆素酮、8-烯丙基香豆素酮。
• ——
  作者：A. Yu. Tolmachev、N. Ya. Podkhalyuzina、N. A. Kuznetsova、V. F. Traven'

  DOI：10.1023/a:1012434702051

  日期：——

  A new procedure was developed for the synthesis of 8-alkoxycarbonylangelieins by base-catalyzed cyclization of ortho-acyl(hydroxy)coumarins with haloacetic acid esters. The procedure was successfully applied to prepare a series of new 8-alkoxycarbonyl- and 8-acylangelicins.
• Threshold Dependence of Mortality Effects for Fine and Coarse Particles in Phoenix, Arizona
  作者：Richard L. Smith、Dan Spitzner、Yuntae Kim、Montserrat Fuentes

  DOI：10.1080/10473289.2000.10464172

  日期：2000.8

  Daily data for fine (<2.5 mu m) and coarse (2.5-10 mu m) particles are available for 1995-1997 from the U.S. Environmental Protection Agency (EPA) research monitor in Phoenix, AZ. Mortality effects on the 65 and over population were studied for both the city of Phoenix and for a region of about 50 mi around Phoenix. Coarse particles in Phoenix are believed to be natural in origin and spatially homogeneous, whereas fine particles are primarily vehicular in origin and concentrated in the city itself. For this reason, it is natural to focus on city mortality data when considering fine particles, and on region mortality data when considering coarse particles, and most of the results reported here correspond to those assignments.After allowing for seasonality and long-term trend through a nonlinear (B-spline) trend curve, and also for meteorological effects based on temperature and specific humidity, a regression of mortality was performed on PM using several different measures for PM. Based on a linear PM effect, we found a statistically significant coefficient for coarse particles, but not for fine particles, contrary to what is widely believed about the effects of coarse and fine particles. An analysis of nonlinear pollution-mortality relationships, however, suggests that the true picture is more complicated than that. For coarse particles, the evidence for any nonlinear or threshold-based effect is slight. For fine particles, we found evidence of a threshold, most likely with values in the range of 20-25 mu g/m(3). We also found some evidence of interactions of the PM effects with season and year.The main effect here is an apparent seasonal interaction in the coarse PM effect. An attempt was made to explain this in terms of seasonal variation in the chemical composition of PM, but this led to another counterintuitive result: the PM effect is highest in spring and summer, when the anthropogenic concentration of coarse PM is lowest as determined by a principal components analysis. There was no evidence of confounding between the fine and coarse PM effects. Although these results are based on one city and should be considered tentative until replicated in other studies, they suggest that the prevailing focus on fine rather than coarse particles may be an oversimplification. The study also shows that consideration of nonlinear effects can lead to real changes of interpretation and raises the possibility of seasonal effects associated with the chemical composition of PM.