(3-bromo-4-methoxyphenyl)-phenylmethanone | 116413-49-1

• 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: (3-bromo-4-methoxyphenyl)-phenylmethanone
• 英文别名: 3-bromo-4-methoxybenzophenone
• CAS: 116413-49-1
• 化学式: C₁₄H₁₁BrO₂
• mdl: MFCD02253215
• 分子量: 291.144
• InChiKey: SGPFOQDTPIYOFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-bromo-4-methoxyphenyl)-phenylmethanone 在 aluminum (III) chloride 作用下， 生成 4-羟基-二苯甲酮
  参考文献：
  名称：

  Synthesis and biological evaluation of negative allosteric modulators of the Kv11.1(hERG) channel

  摘要：

  We synthesized and evaluated a series of compounds for their allosteric modulation at the K(v)11.1 (hERG) channel. Most compounds were negative allosteric modulators of [H-3]dofetilide binding to the channel, in particular 7f, 7h-j and 7p. Compounds 7f and 7p were the most potent negative allosteric modulators amongst all ligands, significantly increasing the dissociation rate of dofetilide in the radioligand kinetic binding assay, while remarkably reducing the affinities of dofetilide and astemizole in a competitive displacement assay. Additionally, both 7f and 7p displayed peculiar displacement characteristics with Hill coefficients significantly distinct from unity as shown by e.g., dofetilide, further indicative of their allosteric effects on dofetilide binding. Our findings in this investigation yielded several promising negative allosteric modulators for future functional and clinical research with respect to their antiarrhythmic propensities, either alone or in combination with known K(v)11.1 blockers. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.10.032
• 作为产物：
  描述：

  4-甲氧基二苯甲酮 在 溴 、 sodium acetate 、 溶剂黄146 作用下， 生成 (3-bromo-4-methoxyphenyl)-phenylmethanone
  参考文献：
  名称：

  Blakey; Jones; Scarborough, Journal of the Chemical Society, 1927, p. 2869

  摘要：

  DOI：

文献信息

• Iodine-catalyzed disproportionation of aryl-substituted ethers under solvent-free reaction conditions
  作者：Marjan Jereb、Dejan Vražič

  DOI：10.1039/c3ob27267b

  日期：——

  iodine produced triphenylmethane and the corresponding aldehydes and ketones. The electron-donating substituents facilitated the reaction, while the electron-withdrawing groups retarded it; the difference in reactivity is not very high. Such an observation may be in favour of hydride transfer, predominantly from the less electron rich side of the ether with more stable carbocation formation. With the isotopic

  碘被证明是在无溶剂反应条件下芳基取代的醚歧化的有效催化剂。将各种取代的1,1,1'，1'-四芳基二甲基醚转化为相应的二芳基酮和二芳基甲烷衍生物。由I 2催化的4-甲氧基苯基取代的醚的转化也产生了单烷基化和二烷基化的Friedel-Crafts产品。用催化量的碘处理三苯甲基烷基和三苯甲基苄基醚三苯甲烷以及相应的醛和酮。供电子的取代基促进了反应，而吸电子基团阻止了该反应。反应性差异不是很大。这种观察可能有利于氢化物转移，主要是从醚的电子富集较少的一侧开始，具有更稳定的碳正离子形成。通过同位素研究，可以确定，大部分的C–H键断裂在速率确定步骤中发生，而羰基氧原子则起源于起始醚，而不是空气。转化是在空气和氩气下进行的，HI不是起作用的催化剂。
• Esters as Acylating Reagent in a Friedel−Crafts Reaction: Indium Tribromide Catalyzed Acylation of Arenes Using Dimethylchlorosilane
  作者：Yoshihiro Nishimoto、Srinivasarao Arulananda Babu、Makoto Yasuda、Akio Baba

  DOI：10.1021/jo801914x

  日期：2008.12.5

  The Friedel-Crafts acylation of arenes with esters by dimethylchlorosilane and 10 mol % of indium tribromide has been achieved. The key intermediate RCOOSi(Cl)Me(2) is generated from alkoxy esters with the evolution of the corresponding alkanes. The scope of the alkoxy ester moiety was wide: tert-butyl, benzyl, allyl, and isopropyl esters were successful. In addition, we demonstrated the direct synthesis

  已经通过二甲基氯硅烷和10mol％的三溴化铟实现了芳烃与酯的弗瑞德-克来福特酰化。关键中间体RCOOSi（Cl）Me（2）由烷氧基酯生成，并伴随有相应的烷烃生成。烷氧基酯部分的范围很广：叔丁基酯，苄基酯，烯丙基酯和异丙酯是成功的。此外，我们证明了由酯10直接合成丹参戊醇的茚满酮中间体11。
• Synthesis and catalytic reactivity in Friedel–Crafts acylations of monobridged bis(cyclopentadienyl)molybdenum(I) carbonyl complexes
  作者：Xin Long Yan、Ning Zhang、Zhi Qiang Hao、Zhi Hong Ma、Zhan Gang Han、Xue Zhong Zheng、Jin Lin

  DOI：10.1016/j.poly.2018.03.021

  日期：2018.6

  analysis. Friedel–Crafts acylation reactions of anisole derivatives with aromatic or aliphatic acyl chlorides catalyzed by complexes 4–6 showed that all of these monobridged bis(cyclopentadienyl)molybdenum carbonyl complexes have catalytic activity.

  摘要当单桥双环戊二烯（C5H5）R（C5H5）[R = C（CH3）2（1），Si（CH3）2（2），C（CH2）5（3）]与Mo（CO）6反应时回流二甲苯，相应的配合物[（η5-C5H4）2R] [Mo（CO）3] 2 [R = C（CH3）2（4），Si（CH3）2（5），C（CH2）5（6 ）]。这些配合物通过色谱分离，并通过元素分析，IR和1H NMR光谱进行表征。通过X射线衍射分析确定4和5的分子结构。配合物4-6催化苯甲醚衍生物与芳族或脂肪族酰氯的Friedel-Crafts酰化反应表明，所有这些单桥双（环戊二烯基）钼羰基配合物均具有催化活性。
• Organic Superbase <i>t</i>-Bu-P4 Catalyzes Amination of Methoxy(hetero)arenes
  作者：Masanori Shigeno、Kazutoshi Hayashi、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1021/acs.orglett.9b01805

  日期：2019.7.19

  methoxy(hetero)arenes with amine nucleophiles such as aniline, indoline, and aminopyridine derivatives. This catalytic reaction is effective for the transformation of electron-deficient methoxyarenes possessing diverse functionalities (carbonyl, cyano, nitro, and halogen) as well as methoxyheteroarenes, including pyrazine, quinoline, isoquinoline, and pyridine derivatives. Intramolecular reactions provide six- and

  我们报告有机超碱t -Bu-P4有效地催化了胺类亲核试剂（如苯胺，二氢吲哚和氨基吡啶衍生物）对甲氧基（杂）芳烃的胺化作用。该催化反应对于转化具有不足功能（羰基，氰基，硝基和卤素）的缺电子的甲氧基芳烃以及包括吡嗪，喹啉，异喹啉和吡啶衍生物的甲氧基杂芳烃是有效的。分子内反应提供六元和七元环胺产物。
• Pharmacokinetics of Gepirone in Subjects with Normal Renal Function and in Patients with Chronic Renal Dysfunction
  作者：Peter Dogterom、Jan A.M. Huisman、Ryszard Gellert、Aalt Verhagen

  DOI：10.2165/00044011-200222080-00003

  日期：——

  Objective: To compare the pharmacokinetic profiles of gepirone and its main metabolites, 1-(2-pyrimidinyl)-piperazine (1-PP) and the 3′-hydroxy derivative (3′-OH-gepirone) after a single oral dose of gepirone extended-release (gepirone-ER) in subjects with normal renal function and in patients with various levels of renal dysfunction. Design: Open-label, parallel-group, single oral dose pharmacokinetic study. Participants: 37 subjects, aged 35 to 65 years with normal renal function (n = 9) or mild (n = 9), moderate (n = 9) or severe (n = 10) renal impairment Methods: All subjects received a single oral dose of gepirone-ER (two 20mg tablets) under fasting conditions. Participants were matched with regard to age and body mass index. Serial blood samples were drawn over 96 hours to measure plasma concentrations of gepirone, 1-PP and 3′-OH-gepirone. Urine was collected to assess the excretion of gepirone and its metabolites. Results: The exposure [area under the plasma concentration-time curve (AUC), maximum plasma concentration (Cmax)] to gepirone, 1-PP and 3′-OH-gepirone increased with decreasing renal function. The AUC of gepirone and its metabolites was greatest in patients with the severest renal dysfunction. No difference was observed in the elimination half-life (t1/2) of gepirone, but the t1/2 of the metabolites was longer in patients with severe dysfunction than in those with normal renal function. Renal clearance of gepirone, 1-PP and 3′-OH-gepirone was higher in those with normal function than in patients with severe dysfunction. Adverse events (18) occurred more frequently only in subjects with severe renal impairment. Conclusions: Gepirone-ER was generally well tolerated among patients with varying degrees of renal impairment. Exposure to gepirone and its metabolites was increased by renal impairment, especially in subjects with severe dysfunction. Therefore, caution should be used when selecting the dose of gepirone in patients with severe renal impairment.

  目标：比较正常肾功能受试者和不同程度肾功能障碍患者服用单剂量吉匹隆缓释剂(gepirone-ER)后,吉匹隆及其主要代谢产物1-(2-嘧啶基)-哌嗪(1-PP)和3'-羟基衍生物(3'-OH-gepirone)的药代动力学特征。 设计：开放标签、平行分组、单剂量药代动力学研究。 参与者：37名35-65岁受试者,包括肾功能正常组(n=9)、轻度(n=9)、中度(n=9)和重度(n=10)肾功能损害组。 方法：所有受试者空腹服用单剂量吉匹隆缓释剂(两片20mg片剂)。根据年龄和体重指数进行分组匹配。96小时内连续采集血样测定吉匹隆、1-PP和3'-OH-gepirone的血浆浓度。收集尿液评估吉匹隆及其代谢产物的排泄。 结果：随着肾功能下降,吉匹隆、1-PP和3'-OH-gepirone的暴露量(血浆浓度-时间曲线下面积AUC、最大血浆浓度Cmax)增加。重度肾功能障碍患者的AUC最大。吉匹隆的消除半衰期(t1/2)无差异,但重度肾功能障碍患者代谢产物的t1/2长于正常肾功能者。正常肾功能者的吉匹隆、1-PP和3'-OH-gepirone肾清除率高于重度肾功能障碍患者。不良事件(18例)仅在重度肾功能障碍受试者中更为常见。 结论：不同程度肾功能障碍患者对吉匹隆缓释剂的耐受性普遍良好。肾功能损害会增加吉匹隆及其代谢产物的暴露量,尤其是重度肾功能障碍患者。因此,对重度肾功能障碍患者选择吉匹隆剂量时应谨慎。