溴苯腈甲醚 | 3336-39-8

• 物质功能分类: 分析化学 - 标准品 - 农残、兽药及化肥类
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 溴苯腈甲醚
• 中文别名: 溴苯腈甲基醚；3,5-二溴-4-甲氧基氰苯
• 英文名称: 3,5-dibromo-4-methoxybenzonitrile
• 英文别名: 2,6-Dibromo-4-cyanoanisol；3.5-Dibrom-4-methoxybenzonitril
• CAS: 3336-39-8
• 化学式: C₈H₅Br₂NO
• 分子量: 290.942
• InChiKey: BUGMOVRSBPGSOS-UHFFFAOYSA-N

物化性质

• 熔点：
  115-117°C
• 闪点：
  4 °C
• 保留指数：
  1654.8
• 稳定性/保质期：
  在常温常压下，该物质保持稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn,F,N
• 安全说明：
  S16,S26,S33,S36/37/39,S60,S61
• 危险类别码：
  R36/37/38
• 海关编码：
  2926909090
• WGK Germany：
  3
• 危险品运输编号：
  UN1262 3/PG 2
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P501,P261,P270,P271,P264,P280,P337+P313,P305+P351+P338,P361+P364,P332+P313,P301+P310+P330,P302+P352+P312,P304+P340+P311,P403+P233,P405
• 危险性描述：
  H301+H311+H331,H315,H319

反应信息

• 作为反应物：
  描述：

  溴苯腈甲醚 在 三甲基铝 、 碳酸氢钠 作用下， 以 异丙醇 为溶剂， 反应 40.5h， 生成 2-(3,5-dibromo-4-methoxyphenyl)-3-(4-methylsulfonylphenyl)-5-(trifluoromethyl)-4H-imidazol-5-ol
  参考文献：
  名称：

  1,2-Diarylimidazoles as Potent, Cyclooxygenase-2 Selective, and Orally Active Antiinflammatory Agents

  摘要：

  Series of 1,2-diarylimidazoles has been synthesized and found to contain highly potent and selective inhibitors of the human COX-2 enzyme. The paper describes a short synthesis of the target 1,2-diarylimidazoles starting with aryl nitriles. Different portions of the diarylimidazole (I) were modified to establish SAR. Systematic variations of the substituents in the aryl ring B have yielded very potent (IC50 = 10-100 nm) and selective (1000-12500) inhibitors of the COX-2 enzyme. The study on the influence of substituents in the imidazole ring established that a CF3 group at position 4 gives the optimum oral activity. A number of the diarylimidazoles showed excellent inhibition in the adjuvant induced arthritis model (e.g., ED50 = 0.02 mph for 22 and 34). The diarylimidazoles are also potent inhibitors of carrageenan-induced edema (ED50 = 9-30 mph) sind hyperalgesia (ED50 = 11-40 mpk). Several orally active diarylimidazoles show no GI toxicity in the rat and mouse up to 200 mpk.

  DOI：

  10.1021/jm9700225

文献信息

• Elongation of Phenoxide C–O Bonds Due to Formation of Multifold Hydrogen Bonds: Statistical, Experimental, and Theoretical Studies
  作者：Naoto Hayashi、Kazuhito Sato、Yuka Sato、Masayuki Iwagami、Naoki Nishimura、Junro Yoshino、Hiroyuki Higuchi、Tohru Sato

  DOI：10.1021/jo200852r

  日期：2011.7.15

  Å). Elongated phenoxide C–O bonds associated with the formation of 3-fold hydrogen bonds were also observed in the X-ray structures of proton-transfer complexes (2X–O–)(TEAH+)s derived from 5′-X-substituted 5,5′′-dimethyl-1,1′:3′,1′′-terphenyl-2,2′,2′′-triols (2X–OHs, where X = NO2, CN, COOCH3, Cl, F, H, and CH3) and triethylamine (TEA). By comparing the X-ray structures, C–O bond elongation was found

  使用剑桥结构数据库的统计研究表明，存在多个拉长的酚盐C–O键。它们的特征是与酚盐氧原子形成3倍（或2倍）氢键，它们的平均键长延伸至1.320Å，这与理论上预测的碳氧键长完全不同。 C 6 H 5 O –（1.26Å）。在5'-X-取代的5衍生的质子转移复合物（2X-O -）（TEAH +）的X射线结构中还观察到与3倍氢键形成相关的伸长的酚盐C-O键。，5''-二甲基-1,1'：3'，1''-三联-2,2'，2''-三醇（2X–OHs，其中X = NO 2，CN，COOCH 3，Cl，F，H和CH 3）和三乙胺（TEA）。通过比较X射线结构，发现对位键（X）的吸电子取代基对C-O键的延伸影响很小。这与N–H（··· – O –）和O–H（··· – O –）拉伸振动中强烈的红移有关，表明（2X–O –）（茶+）本质上具有单键字符。在模型配合物上的分子轨道计算进一步证实了这一点，表明带负电荷的
• Kelly, David P.; Bateman, Stuart A.; Hook, Robert J., Australian Journal of Chemistry, 1994, vol. 47, # 9, p. 1751 - 1770
  作者：Kelly, David P.、Bateman, Stuart A.、Hook, Robert J.、Martin, Roger F.、Reum, Monica E.、et al.

  DOI：——

  日期：——
• COMPOSITIONS AND METHODS FOR TARGETED ENZYMATIC RELEASE OF CELL REGULATORY COMPOUNDS
  申请人：Marker Gene Technologies, Inc.

  公开号：EP1200131A2

  公开（公告）日：2002-05-02
• [EN] COMPOSITIONS AND METHODS FOR TARGETED ENZYMATIC RELEASE OF CELL REGULATORY COMPOUNDS<br/>[FR] COMPOSITIONS ET PROCEDES POUR LA LIBERATION ENZYMATIQUE CIBLEE DE COMPOSES REGULATEURS DE CELLULES
  申请人：MARKER GENE TECHNOLOGIES INC

  公开号：WO2001002020A2

  公开（公告）日：2001-01-11

  Novel pro-drugs and methods for their use to alter the growth and biological characteristics of living cells, tissues, or whole organisms are described. The methods allow for selective activation of the pro-drugs at or near transformant host cells expressing a gene for an enzyme that activates the pro-drugs. Pro-drugs according to a preferred embodiment of the invention are conjugates of a bioactive compound and a chemical group that is capable of being cleaved from the bioactive compound by action of an enzyme. Methods according to this invention include: (a) introducing into targeted cells a gene encoding an enzyme and (b) administering a pro-drug, wherein the enzyme releases the pro-drug from conjugation. In a preferred embodiment of the invention, the gene encoding the enzyme is a marker gene.
• 1,2-Diarylimidazoles as Potent, Cyclooxygenase-2 Selective, and Orally Active Antiinflammatory Agents
  作者：Ish K. Khanna、Richard M. Weier、Yi Yu、Xiang D. Xu、Francis J. Koszyk、Paul W. Collins、Carol M. Koboldt、Amy W. Veenhuizen、William E. Perkins、Jacquelen J. Casler、Jaime L. Masferrer、Yan Y. Zhang、Susan A. Gregory、Karen Seibert、Peter C. Isakson

  DOI：10.1021/jm9700225

  日期：1997.5.1

  Series of 1,2-diarylimidazoles has been synthesized and found to contain highly potent and selective inhibitors of the human COX-2 enzyme. The paper describes a short synthesis of the target 1,2-diarylimidazoles starting with aryl nitriles. Different portions of the diarylimidazole (I) were modified to establish SAR. Systematic variations of the substituents in the aryl ring B have yielded very potent (IC50 = 10-100 nm) and selective (1000-12500) inhibitors of the COX-2 enzyme. The study on the influence of substituents in the imidazole ring established that a CF3 group at position 4 gives the optimum oral activity. A number of the diarylimidazoles showed excellent inhibition in the adjuvant induced arthritis model (e.g., ED50 = 0.02 mph for 22 and 34). The diarylimidazoles are also potent inhibitors of carrageenan-induced edema (ED50 = 9-30 mph) sind hyperalgesia (ED50 = 11-40 mpk). Several orally active diarylimidazoles show no GI toxicity in the rat and mouse up to 200 mpk.

表征谱图