(3-chloro-4-methoxyphenyl)(phenyl)methanone | 10547-61-2

• 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: (3-chloro-4-methoxyphenyl)(phenyl)methanone
• 英文别名: (3-Chloro-4-methoxyphenyl)-phenylmethanone
• CAS: 10547-61-2
• 化学式: C₁₄H₁₁ClO₂
• mdl: MFCD01464001
• 分子量: 246.693
• InChiKey: IGNLOYXQTDSIAQ-UHFFFAOYSA-N

物化性质

• 熔点：
  99°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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-chloro-4-methoxyphenyl)(phenyl)methanone 在 氢溴酸 、 溶剂黄146 作用下， 生成 (3,5-二氯-4-羟基苯基)苯基-甲酮
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基二苯甲酮 在 氯 、 溶剂黄146 作用下， 生成 (3-chloro-4-methoxyphenyl)(phenyl)methanone
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• 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。
• Catalytic C(sp²)–C(sp³) Bond Formation of Methoxyarenes by the Organic Superbase <i>t</i>-Bu-P4
  作者：Masanori Shigeno、Kazutoshi Hayashi、Kanako Nozawa-Kumada、Yoshinori Kondo

  DOI：10.1021/acs.orglett.0c03507

  日期：2020.11.20

  [cyano, nitro, (non)enolizable ketone, chloride, and amide moieties] are allowed on methoxyarenes. Moreover, an array of alkanenitriles with/without an aryl moiety at the nitrile α-position can be employed. The system also features no requirement of a stoichiometric base, MeOH (not salt waste) formation as a byproduct, and the production of congested quaternary carbon centers.

  有机超碱催化剂t -Bu-P4实现了烷烃前亲核体对甲氧基芳烃的亲核芳族取代。在甲氧基芳烃上可以使用各种官能团[氰基，硝基，（不可）烯化的酮，氯和酰胺部分）。此外，可以使用在腈α-位具有/不具有芳基部分的链烷腈的阵列。该系统还不需要化学计量的碱，不需要的副产物MeOH（无盐废料）形成以及拥挤的季碳中心的生产。
• Lithiation of 2-Aryl-2-(chloroaryl)-1,3-dioxolanes and Its Application in the Synthesis of Newortho-Functionalized Benzophenone Derivatives
  作者：Gyula Lukács、Márta Porcs-Makkay、Gyula Simig

  DOI：10.1002/ejoc.200400335

  日期：2004.10

  2-Aryl-2-(chloroaryl)-1,3-dioxolanes 4 were lithiated ortho to the ketal group of the chloroaryl ring by treatment with butyllithium in THF between −78 and 0 °C. The site selectivity of some of the deprotonation reactions was rationalized by the long-range effect of the 4-chloro substituent. The lithio species thus generated were treated with various electrophiles to give ortho-functionalized benzophenone

  2-芳基-2-(氯芳基)-1,3-二氧戊环 4 通过在-78 和 0 °C 之间的 THF 中用丁基锂处理，在氯芳基环的缩酮基团的邻位锂化。一些去质子化反应的位点选择性通过 4-氯取代基的长程效应合理化。用各种亲电试剂处理由此产生的锂硫物质，得到邻位官能化的二苯甲酮衍生物。在 2-(4-氯苯基)-2-(4-氟苯基)-1,3-二氧戊环 (4s) 的锂化过程中观察到芳环之间的分子内竞争。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• 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。