[4-(2-溴乙氧基)苯基]-(4-甲氧基苯基)甲酮 | 13278-76-7

• 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: [4-(2-溴乙氧基)苯基]-(4-甲氧基苯基)甲酮
• 英文名称: 4-(2-bromoethoxy)-4'-methoxybenzophenone
• 英文别名: 4-Methoxy-4'-(2-bromoethoxy)benzophenone；4-(2-bromaethoxy)-4'-methoxybenzophenon；[4-(2-Bromoethoxy)phenyl](4-methoxyphenyl)methanone；[4-(2-bromoethoxy)phenyl]-(4-methoxyphenyl)methanone
• CAS: 13278-76-7
• 化学式: C₁₆H₁₅BrO₃
• 分子量: 335.197
• InChiKey: OMSGWUYZQSTNSI-UHFFFAOYSA-N

物化性质

• 沸点：
  459.6±40.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [4-(2-溴乙氧基)苯基]-(4-甲氧基苯基)甲酮 在 氢氧化钾 、 碘 、 四丁基硫酸氢铵 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 12.5h， 生成 2-phenoxy>-N-ethylpyrrolidin-2-one
  参考文献：
  名称：

  Estrogen receptor binding and estrogenic/antiestrogenic effects of two new metabolites of nitromiphene, 2-[p-[2-nitro-1-(4-methoxyphenyl)-2-phenylvinyl]phenoxy]-N-ethylpyrrolidine

  摘要：

  Reduction of the triarylethylene antiestrogen 2-[p-[2-nitro-1-(4-methoxphenyl)-2-phenylvinyl]phenoxy]-N-ethylpyrrolidine (1) with sodium borohydride-stannous chloride afforded 2-(p-methoxyphenyl)-p'-(2-pyrrolidin-1-ylethoxy)deoxybenzoin (2). Incubation of 1 with rat cecal content suspension under aerobic or anaerobic conditions also resulted in the generation of 2. The lactam analogue of 1 (6) was prepared by condensation of 4-(2-bromoethoxy)-4'-methoxybenzophenone (3) with benzylmagnesium chloride, followed by dehydration, amidation with 2-pyrrolidinone, and nitration. A metabolite with chromatographic and spectral properties identical with those of 6 was found in extracts from incubation mixtures of 1 with phenobarbital-induced rat liver 9000g supernatant. Compound 2 did not exhibit appreciable binding to the rat uterine cytosol estrogen receptor at concentrations of up to 1 X 10(-6) M and had no estrogenic or antiestrogenic activity in the 3-day rat uterotropic assay. By contrast, 6 had estrogen receptor affinity somewhat greater than that of 1 and slightly greater estrogenic activity accompanied by reduced antiestrogenic activity in comparison with those of 1.

  DOI：

  10.1021/jm00366a008
• 作为产物：
  描述：

  对甲氧基苯甲酰氯 、 2-苯氧乙基溴 在 aluminum (III) chloride 盐酸 、 水 作用下， 以 硝基苯 为溶剂， 反应 2.08h， 以86%的产率得到[4-(2-溴乙氧基)苯基]-(4-甲氧基苯基)甲酮
  参考文献：
  名称：

  Preparation of prodrugs for selective drug delivery

  摘要：

  合成具有A-B-C化学式的化合物，可用于药物传递等应用，其中A是化学发光基团，B是光致变色基团，C是生物活性基团，其中A-B-C可作为前药。本发明的新型合成方法用于形成前药，包括以下步骤：(1)形成苯酮，(2)形成二芳基乙烯，(3)将邻苯二甲酰亚胺基团连接到乙烯的至少一个芳基上，形成邻苯二甲酰亚胺-乙烯共轭物，(4)缩合两个乙烯-邻苯二甲酰亚胺共轭物，形成邻苯二甲酰亚胺-戊二烯共轭物，(5)通过与肼反应将邻苯二甲酰亚胺转化为邻苯二酰肼，形成本发明的载体化合物，(6)将载体化合物与药物的亲核基团反应，形成相应的前药。另外，可以通过使用卤代二芳基乙烯制备相应的阳离子类似的类似类似染料化合物。然后，通过与亲核试剂反应保护阳离子类似化合物，并通过钯催化的胺化与氨基邻苯二甲酰亚胺偶联，形成保护的邻苯二甲酰亚胺-戊二烯共轭物。后者与肼回流，将其邻苯二甲酰亚胺转化为邻苯二酰肼，并酸化以得到载体。本发明的另一个方面涉及将这些化合物用作抗病毒剂，用于治疗病毒感染，如HIV，以及用作抗癌剂，用于治疗结肠癌、肺癌和乳腺癌等癌症。

  公开号：

  US20050080260A1

文献信息

• Synthesis and Chiral Separation of Some Antitumor Agents
  作者：Satendra Singh、Karen L. Meyer、Robert A. Magarian

  DOI：10.1006/bioo.1996.0009

  日期：1996.3

  Four Z-isomers of 1,1-dichloro-2,2,3-triarylcyclopropane (DTACs), designed as potent antitumor agents, were synthesized from their appropriately substituted ethenes, which were prepared from the Grignard reaction followed by the dehydration of their intermediate carbinols. The stereospecific addition of dichlorocarbene to the ethenes followed by fractional crystallization afforded (Z)-1,1-dichloro-2-(4-benzyloxyphenyl)-2-(4-methoxyphenyl)-3- phenylcyclopropane and (Z)-1,1-dichloro-2,3-diphenyl-2-(4-methoxyphenyl) cyclopropane. Displacement of the bromo group from the ethoxy side chain intermediates with dimethylamine gave the desired basic side chain compounds, (Z)-1,1-dichloro-2,3-diphenyl-2-[4-(2- dimethylaminoethoxy)phenyl] cyclopropane and (Z)-1,1-dichloro-2- [4-(2-dimethylaminoethoxy)phenyl]-2- (4-methoxyphenyl)-3-phenylcyclopropane. While both E- and Z-stereoisomers of the DTACs were isolated using fractional crystallization, only the Z-compounds were resolved on a chiral stationary phase consisting of amylose tris-3,5-dimethylphenyl carbamate coated on silica gel. Complete resolution of the E-compounds was not observed with this system. (C) 1996 Academic Press, Inc.