(4-甲氧基-3-甲基苯基)乙酰氯 | 4513-72-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (4-甲氧基-3-甲基苯基)乙酰氯
• 英文名称: 4-methoxy-3-methylphenylacetyl chloride
• 英文别名: (4-methoxy-3-methyl-phenyl)-acetyl chloride；<4-Methoxy-3-methyl-phenyl>-acetylchlorid；2-(4-Methoxy-3-methylphenyl)acetyl chloride
• CAS: 4513-72-8
• 化学式: C₁₀H₁₁ClO₂
• 分子量: 198.649
• InChiKey: LKSNEELUPOSMJO-UHFFFAOYSA-N

物化性质

• 沸点：
  279.9±28.0 °C(Predicted)
• 密度：
  1.161±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  (4-甲氧基-3-甲基苯基)乙酰氯 在 sodium azide 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 生成 (4-Methoxy-3-methyl-phenyl)-acetyl azide
  参考文献：
  名称：

  Orally active .beta.-lactam inhibitors of human leukocyte elastase-1. Activity of 3,3-diethyl-2-azetidinones

  摘要：

  A thorough analysis of the mechanism of inhibition of human leukocyte elastase (HLE) by a monocyclic beta-lactam and the mechanism of beta-lactam hydrolysis led to the preparation of potent and highly stable inhibitors of HLE. This work led to the identification of 4-[(4-carboxyphenyl)-oxy]-3,3-diethyl-1-[[(phenylmethyl)amino]carbonyl]-2-azetidinone (2) as the first orally active inhibitor of human leukocyte elastase (HLE). Analogs of 2 with different substituents on the urea N were synthesized and evaluated for their activity in vitro against HLE as well as in vivo in a hamster lung hemorrhage model. Compounds with a methyl or a methoxy group in the para position of the benzene ring were very potent in both assays. The results are discussed on the basis of the proposed model for the binding of this class of inhibitors to HLE and a possible mechanism of inhibition is presented.

  DOI：

  10.1021/jm00099a003
• 作为产物：
  描述：

  2-甲基苯甲醚 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 苄基三甲基氢氧化铵 作用下， 以 1,4-二氧六环 、 甲醇 、 三氟乙酸 、 苯 为溶剂， 反应 10.5h， 生成 (4-甲氧基-3-甲基苯基)乙酰氯
  参考文献：
  名称：

  Studies on ketene and its derivatives. CIX. Synthesis of naturally occurring anthracene-9,10-diones.

  摘要：

  本文介绍了从 2-苄基-4，6-二羟基苯甲酸乙酯（7a-d）合成天然蒽-9，10-二酮（12a-c）的方法，该方法由二酮烯与 4-芳基-3-氧代丁酸乙酯（6a-d）反应制备。在氢化钠存在下，二酮烯与 6a-d 在四氢呋喃中反应，得到 7a-d。在碳酸钾存在下用碘甲烷处理 7a-d，然后用乙醇氢氧化钠处理，得到 2-苄基-4，6-二甲氧基苯甲酸（9a-d）。9a-d 与三氟乙酸-三氟乙酸酐环化后得到蒽酮衍生物 (10a-d)，无需纯化，用三氧化铬氧化后得到蒽-9，10-二酮 (11a-d)。用三溴化硼对 11a-c 进行选择性去甲基化，得到 12a-c。

  DOI：

  10.1248/cpb.30.2440

文献信息

• Synthesis of substituted spiro[4.5]deca-3,6,9-triene-2,8-diones: an expeditious route to the spiro[4.5]decane terpene skeleton
  作者：Richard A. Haack、Kenneth R. Beck

  DOI：10.1016/s0040-4039(00)99532-7

  日期：1989.1

  Substituted spiro[4.5]decanes are prepared in two steps in fair to moderate yield. A substituted 4-methoxyphenylacetyl chloride, prepared from the corresponding acid, is reacted with a substituted acetylene (or acetylene gas) in the presence of aluminum chloride in methylene chloride at 0°C to produce the corresponding substituted spiro derivative.

  分两步制备取代的螺[4.5]癸烷，以中等至中等的产率制备。由相应的酸制得的取代的4-甲氧基苯基乙酰氯在0℃的二氯甲烷中在氯化铝的存在下与取代的乙炔（或乙炔气）反应生成相应的取代的螺衍生物。
• A new approach to (±)-heritonin. The preparation of β-tetralones from allylsilanes and acid chlorides
  作者：Claudio C. Silveira、Alessandra Machado、Antonio L. Braga、Eder João Lenardão

  DOI：10.1016/j.tetlet.2004.03.154

  日期：2004.5

  A new method for the preparation of 4-alkyl-β-tetralones is described, by reaction of arylacetic acid chlorides with allylsilanes. Employing β-tetralone 5, the synthesis of (±)-heritonine and (±)-epi-heritonine, natural piscicides isolated from Heritiera littoralis, was achieved in four steps and 22% overall yield. The key step of this synthesis involved the selenocarbenium ion-mediated elaboration

  描述了一种通过芳基酰氯与烯丙基硅烷反应制备4-烷基-β-四氢萘酮的新方法。采用β四氢萘酮5，（±）-heritonine和（±）的合成-外延-heritonine，分离自天然杀鱼银叶树，在四个步骤和22％达到总产率。该合成的关键步骤涉及硒代碳鎓离子介导的天然产物丁烯内酯环的修饰。
• ORGANIC COMPOUNDS
  申请人：Nozulak Joachim

  公开号：US20090099243A1

  公开（公告）日：2009-04-16

  The invention relates to compound of the formula (I) in which the substituents are as defined in the specification; in free base form or in acid addition salt form; to its preparation, to its use as medicament and to medicaments comprising it.

  本发明涉及式(I)的化合物，其中取代基如规范中所定义；以自由碱或酸盐形式存在；其制备方法，以及其作为药物的用途和包含它的药物。
• Discovery of a Potent, Selective T-type Calcium Channel Blocker as a Drug Candidate for the Treatment of Generalized Epilepsies
  作者：Olivier Bezençon、Bibia Heidmann、Romain Siegrist、Simon Stamm、Sylvia Richard、Davide Pozzi、Olivier Corminboeuf、Catherine Roch、Melanie Kessler、Eric A. Ertel、Isabelle Reymond、Thomas Pfeifer、Ruben de Kanter、Michael Toeroek-Schafroth、Luca G. Moccia、Jacques Mawet、Richard Moon、Markus Rey、Bruno Capeleto、Elvire Fournier

  DOI：10.1021/acs.jmedchem.7b01236

  日期：2017.12.14

  We report here the discovery and pharmacological characterization of N-(1-benzyl-1H-pyrazol-3-yl)-2-phenylacetamide derivatives as potent, selective, brain-penetrating T-type calcium channel blockers. Optimization focused mainly on solubility, brain penetration, and the search for an aminopyrazole metabolite that would be negative in an Ames test. This resulted in the preparation and complete characterization of compound 66b (ACT-709478), which has been selected as a clinical candidate.
• Novel 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues as cytotoxic agents
  作者：Vedula M. Sharma、K.V. Adi Seshu、C. Vamsee Krishna、P. Prasanna、V. Chandra Sekhar、A. Venkateswarlu、Sriram Rajagopal、R. Ajaykumar、Dhanvanthri S. Deevi、N.V.S. Rao Mamidi、R. Rajagopalan

  DOI：10.1016/s0960-894x(03)00263-4

  日期：2003.5

  A series of 6,7-diphenyl-2,3,8,8a-tetrahydro-1H-indolizin-5-one analogues were synthesized and evaluated for cytotoxic activity against eight human cancer cell lines. Compounds 18, 21, 28, 29, 30 and 31 showed cytotoxic activity with GI(50) values in the range of 2.1-8.1 muM concentration. Among these, compounds 21 and 28 exhibited good pharmacokinetic properties. These compounds were further evaluated for their in vivo efficacy in modified hollow fibre assay (HFA). (C) 2003 Elsevier Science Ltd. All rights reserved.