bromomagnesium phenolate | 35770-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bromomagnesium phenolate
• 英文别名: Phenoxymagnesium bromide；Bromomagnesium phenolate；magnesium;bromide;phenoxide
• CAS: 35770-74-2
• 化学式: Br*C₆H₅O*Mg
• 分子量: 197.314
• InChiKey: MDICRVQYTYKOIL-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -2.62
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  bromomagnesium phenolate 在 4-二甲氨基吡啶 、 Jones reagent 、 水 、 potassium carbonate 、 sodium iodide 、 sodium hydroxide 、 N,N'-二异丙基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 74.0h， 生成 7-{4-[4-(7-phenyloxyheptyloxy)]benzoyloxy}benzoyloxynaphthalen-2-yl 4-(4-dodecyloxybenzoyloxy)benzoate
  参考文献：
  名称：

  Bent-core mesogens with an aromatic unit at the terminal position

  摘要：

  具有萘中心单元和分子链末端位置芳香环的弯曲核液晶被合成，旨在增强纳米分离。

  DOI：

  10.1039/c6nj03908a
• 作为产物：
  描述：

  苯酚 在 乙基溴化镁 作用下， 以 四氢呋喃 为溶剂， 生成 bromomagnesium phenolate
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 3-Aryloxindoles:  A New Class of Calcium-Dependent, Large Conductance Potassium (Maxi-K) Channel Openers with Neuroprotective Properties

  摘要：

  A series of 3-aryloxindole derivatives were synthesized and evaluated as activators of the cloned maxi-K channel mSlo expressed in Xenopus laevis oocytes using electrophysiological methods. The most promising maxi-K openers to emerge from this study were (+/-)-3(5-chloro-2-hydroxyphenyl)-1,3-dihydro-3-hydroxy-6-(trifluoromethyl)-2H-indol-2-one ((+/-)-8c) and its 3-deshydroxy analogue (+/-)-11b. The individual enantiomers of (+/-)-8c were synthesized, and the maxi-K channel-opening properties were shown to depend on the absolute configuration of the single stereogenic center with the efficacy of (-)-8c superior to that of both (+)-8c and the racemic mixture when evaluated at a concentration of 20 muM. Racemic 11b exhibited greater efficacy than either the racemic Se or the more active enantiomer in the electrophysiological evaluation. In vitro metabolic stability studies conducted with (+/-)-8c and (+/-)-11b in rat liver S9 microsomal fractions revealed significant oxidative degradation with two hydroxylated metabolites observed by liquid chromatography/mass spectrometry for each compound in addition to the production of Se from 11b. The pharmacokinetic properties of (+/-)-8c and (+/-)11b were determined in rats as a prelude to evaluation in a rat model of stroke that involved permanent occlusion of the middle cerebral artery (MCAO model). In the MCAO model, conducted in the spontaneously hypertensive rat, the more polar 3-hydroxy derivative (+/-)-8c did not demonstrate a significant reduction in cortical infarct volume when administered intravenously at doses ranging from 0.1 to 10 mg/kg as a single bolus 2 h after middle cerebral artery occlusion when compared to vehicle-treated controls. In contrast, intravenous administration of (+/-)-11b at a dose of 0.03 mg/kg was found to reduce the measured cortical infarct volume by approximately 18% when compared to vehicle-treated control animals. Intraperitoneal administration of (+/-)-11b at a dose of 10 mg/kg 2 h following artery occlusion was shown to reduce infarct volume by 26% when compared to vehicle-treated controls. To further probe the effects of compounds (+/-)-8c and (+/-)-11b on neurotransmitter release in vitro, both compounds were examined for their ability to reduce electrically stimulated [H-3]-glutamate release from rat hippocampal slices that had been preloaded with [H-3]-glutamate. Only (+/-) 11b was able to demonstrate a significant inhibition [3H]-glutamate release in this assay at a concentration of 20 muM, providing concordance with the profile of these compounds in the MCAO model. Although (+/-)-11b showed some promise as a potential developmental candidate for the treatment of the sequelae of stroke based on its efficacy in the rat MCAO model, the pharmacokinetic profile of this compound was considered to be less than optimal and was not pursued in favor of derivatives with enhanced metabolic stability.

  DOI：

  10.1021/jm0101850
• 作为试剂：
  描述：

  对甲酚 、 苯乙炔 在 bromomagnesium phenolate 作用下， 以 xylene 为溶剂， 生成 4-甲基-2-(1-苯基乙烯基)苯酚
  参考文献：
  名称：

  Selectiveo-Vinylation of Phenols; Synthesis of 2-(1-Phenylethenyl)-phenols

  摘要：

  DOI：

  10.1055/s-1977-24292

文献信息

• PHOSPHINE COMPOUND, PROCESS FOR PRODUCING THE SAME, AND PEROXIDE SCAVENGER USING THE SAME
  申请人：Shioji Kosei

  公开号：US20110015440A1

  公开（公告）日：2011-01-20

  The invention provides a novel peroxide scavenger comprising a phosphine compound represented by general formula [I]: wherein Z 1 and Z 2 each represents a cyclic group; Ar represents an arylene group; R represents an aliphatic hydrocarbon group; Y represents phosphorus (P), nitrogen (N), or bismuth (Bi); and R 1 , R 2 , and R 3 each represents a cyclic group, particularly a peroxide scavenger that can scavenge peroxides such as reactive oxygen species which are generated in mitochondria upon exposure to oxidative stress and localized in mitochondria. The phosphine compound of the invention is oxidized by the peroxides localized in mitochondria to increase the fluorescence intensity, whereby the peroxides can be scavenged.

  该发明提供了一种新型过氧化物清除剂，包括由通式[I]所表示的膦化合物：其中Z1和Z2分别表示环状基团；Ar表示芳基基团；R表示脂肪烃基团；Y表示磷（P）、氮（N）或铋（Bi）；而R1、R2和R3分别表示环状基团，特别是一种过氧化物清除剂，可以清除在暴露于氧化应激时在线粒体中生成并定位在线粒体中的反应性氧化物种，该发明的膦化合物被定位在线粒体中的过氧化物氧化以增加荧光强度，从而可以清除过氧化物。
• Sulfonyl transfer mechanism in C–S coupling of phenylmagnesium bromide with phenyl arenesulfonates
  作者：Fatma Eroğlu、Didem Kâhya、Ender Erdik

  DOI：10.1016/j.jorganchem.2009.09.044

  日期：2010.1

  The kinetics of C–S coupling of phenylmagnesium bromide with phenyl arenesulfonates has been studied in THF:toluene (7:10) at 90 °C. Kinetic data and Hammett relationship are consistent with an asynchronous SNa mechanism in which rate determining thiophilic attack of carbanion takes place much ahead of phenoxy group departure.

  已经在90°C的THF：甲苯（7:10）中研究了溴化镁与苯基芳烃磺酸盐的C–S偶联动力学。动力学数据和Hammett关系与异步S N相一致，在该机制中，决定碳的硫亲酸攻击的速率远早于苯氧基团离去。
• Ortho-coordinated acylation of phenol systems
  作者：Giovanni Sartori、Giuseppe Casnati、Franca Bigi、Giovanni Predieri

  DOI：10.1021/jo00301a031

  日期：1990.7
• O-Quinonemethide intermediates and their role in coordinated reactions of magnesium phenoxides with .alpha.-branched aliphatic aldehydes
  作者：Giuseppe Casnati、Andrea Pochini、Maria Giuliana Terenghi、Rocco Ungaro

  DOI：10.1021/jo00169a036

  日期：1983.10
• The Reaction of Dialkyl Sulfates with ROMgBr Compounds
  作者：Arthur C. Cope

  DOI：10.1021/ja01321a030

  日期：1934.6