1-(4-methylphenyl)-3-pentanone | 100765-46-6

• 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: 1-(4-methylphenyl)-3-pentanone
• 英文别名: 1-(p-Methylphenyl)pentan-3-one；1-(p-tolyl)-3-pentanone；1-(p-tolyl)pentan-3-one；1-p-tolylpentan-3-one；1-(4-Methylphenyl)pentan-3-one
• CAS: 100765-46-6
• 化学式: C₁₂H₁₆O
• 分子量: 176.258
• InChiKey: KJHTXBFFCBBQCO-UHFFFAOYSA-N

物化性质

• 沸点：
  263.3±9.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-[(Z)-3-ethoxypent-2-enyl]-4-methylbenzene 在 盐酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 10.0h， 生成 1-(4-methylphenyl)-3-pentanone
  参考文献：
  名称：

  Novel Routes to Enol Ethers, Unsymmetrical Ketones, .alpha.-Bromoalkyl Ketones, 1,4-Diketones, 2-Ethoxy-2-cyclopentenones, and .alpha.-Keto Enamines

  摘要：

  Highly regioselective S(N)2' reactions of adducts 6 (readily prepared by reactions of halides with the allyl anion 12 of 11) with Grignard reagents gave enol ethers 13, which were converted (in one-pot reactions from 11) into ketones 14 and alpha-bromoalkyl ketones 15 in good yields. The monoprotected 1,4-diketone derivative 16 (prepared by Michael addition of the allyl anion 12 with methyl vinyl ketone) was converted both into 1,4-diketones 18 and into protected gamma-hydroxyalkyl ketone 20 by selective Grignard reactions, which could be directed either to the carbonyl, or the protected propenoyl, or to both functionalities. The allyl anion 12 with alpha-substituted acetic esters gave alpha-acylated adducts 24, which underwent in situ unfavored endo-trig cyclization upon treatment with NaH and secondary amines, to give 2-ethoxy-2-cyclopentenones 27 and 28 and alpha-keto enamines 25 in good yield. The mechanism for the cyclization is discussed.

  DOI：

  10.1021/jo00128a037

文献信息

• Arylation of Allylic Alcohols in Ionic Liquids Catalysed by a Pd-Benzothiazole Carbene Complex
  作者：Vincenzo Caló、Angelo Nacci、Antonio Monopoli、Michele Spinelli

  DOI：10.1002/ejoc.200390194

  日期：2003.4

  The reaction of aryl bromides with allylic alcohols catalysed by a Pd-benzothiazole carbene complex, in tetrabutylammonium bromide as solvent, leads principally to β-arylated carbonyl compounds. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  芳基溴化物与烯丙醇的反应由 Pd-苯并噻唑卡宾配合物催化，在四丁基溴化铵作为溶剂中，主要产生 β-芳基化羰基化合物。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• 5-Phenyl-Pentanoic Acid Derivatives as Matrix Metalloproteinase Inhibitors for the Treatment of Asthma and Other Diseases
  申请人：Palle Venkata P.

  公开号：US20080194565A1

  公开（公告）日：2008-08-14

  The present invention relates to C ompounds having the structure of Formula I: wherein n is an integer from 1 to 5; R 1 is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, aralkyl, alkoxy, aryloxy, alkenyloxy or alkynyloxy; R 2 is alkenyl, allcynyl, aryl, heterocyclyl, heteroaryl, cycloalkyl, NR 4 R 5 , —NHC(═Y)R 4 , —NHC(═Y)NR 5 R x , —NHC(═O)OR 4 , —NHSO 2 R 4 , C(═Y)NR 4 R 5 , C(═O)OR 6 [wherein Y is oxygen or sulphur], OR 5 , —O(C═O)NR 4 R 5 , O-acyl, S(O) m R 4 , —SO 2 N(R 4 ) 2 , cyano, amidino or guanidino [wherein R 4 is alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heterocyclyl, heteroaryl, aralkyl, heteroarylalkyl, heterocyclylalkyl or cycloalkylalkyl and m is an integer 0-2; R 5 is hydrogen or R 4 ; R x is R 4 or —SO 2 N(R 4 ) 2 and R 6 is hydrogen, alkyl, cycloalkyl, aralkyl, heteroarylalkyl, heterocyclylalkyl or cycloalkylalkyl]; R 3 is hydrogen, fluorine, alkyl, cycloalkylalkyl or aralkyl; A is OH, OR 4 , —OC(═O)NR 4 R 5 , O-acyl, NH 2 , NR 4 R 5 , —NHC(═Y)R 4 , —NHC(═Y)NR 5 R x , —NHC(═O)OR 4 , —NHSO 2 R 4 , and to processes for the synthesis of the same. This invention also relates to pharmacological compositions containing the compounds of the present invention, and methods of treating asthma, rheumatoid arthritis, COPD, rhinitis, osteoarthritis, psoriatic arthritis, psoriasis, pulmonary fibrosis pulmonary inflammation, acute respiratory distress syndrome, perodontitis, multiple sclerosis, gingivitis, atherosclerosis, neointimal proliferation, which leads to restenosis and ischemic heart failure, stroke, renal diseases, tumor metastasis, and other inflammatory disorders characterized by over-expression and over-activation of an matrix metalloproteinase, using the compounds.

  本发明涉及具有以下结构的化合物：其中n是1到5之间的整数；R1是可选择地取代的烷基、烯基、炔基、环烷基、芳基、杂环烷基、杂芳基、芳基烷基、烷氧基、芳氧基、烯基氧基或炔基氧基；R2是烯基、炔基、芳基、杂环烷基、杂芳基、环烷基、NR4R5、—NHC(═Y)R4、—NHC(═Y)NR5Rx、—NHC(═O)OR4、—NHSO2R4、C(═Y)NR4R5、C(═O)OR6[其中Y是氧或硫]、OR5、—O(C═O)NR4R5、O-酰基、S(O)mR4、—SO2N(R4)2、氰基、胺基亚胺基或胍基[其中R4是烷基、烯基、炔基、环烷基、芳基、杂环烷基、杂芳基、芳基烷基、杂芳基烷基、杂环烷基烷基或环烷基烷基，m是0-2的整数；R5是氢或R4；Rx是R4或—SO2N(R4)2，R6是氢、烷基、环烷基、芳基烷基、杂芳基烷基、杂环烷基烷基或环烷基烷基]；R3是氢、氟、烷基、环烷基烷基或芳基烷基；A是OH、OR4、—OC(═O)NR4R5、O-酰基、NH2、NR4R5、—NHC(═Y)R4、—NHC(═Y)NR5Rx、—NHC(═O)OR4、—NHSO2R4等，以及其合成方法。本发明还涉及含有本发明化合物的药理学组合物，以及治疗哮喘、类风湿关节炎、慢性阻塞性肺病、鼻炎、骨关节炎、银屑病性关节炎、牛皮癣、肺纤维化、肺部炎症、急性呼吸窘迫综合征、牙周炎、多发性硬化症、牙龈炎、动脉粥样硬化、新生内膜增生导致再狭窄和缺血性心力衰竭、中风、肾脏疾病、肿瘤转移和其他炎症性疾病的方法，这些疾病特征是矩阵金属蛋白酶的过度表达和过度激活，使用这些化合物。
• Two efficient pathways for the synthesis of aryl ketones catalyzed by phosphorus-free palladium catalysts
  作者：A. Wirwis、J. Feder-Kubis、A.M. Trzeciak

  DOI：10.1016/j.mcat.2017.10.021

  日期：2018.2

  Allylic alcohols, 1-buten-3-ol, 1-penten-3-ol and 1-octen-3-ol, reacted with aryl iodides (iodotoluene, 4-iodotoluene, 4-iodophenol and 4-iodanisole) under Heck reaction conditions to form corresponding saturated aryl ketones in one step. The same products were obtained in a two-step tandem reaction consisted of the Heck coupling of allylic alcohols with aryl iodides, followed by hydrogenation. Reactions

  在Heck反应条件下，烯丙醇1-丁烯-3-醇，1-戊烯-3-醇和1-辛烯-3-醇与芳基碘化物（碘代甲苯，4-碘代甲苯，4-碘苯酚和4-碘苯甲醚）反应一步形成相应的饱和芳基酮 在两步串联反应中获得了相同的产物，该反应由烯丙基醇与芳基碘化物的Heck偶联组成，然后进行氢化。通过用薄荷醇取代的咪唑鎓氯化物改性的无磷钯前体催化反应。通过TEM证实在反应混合物中形成直径高达65nm的结晶钯纳米颗粒。
• [RuCl₂(<i>p-</i>cymene)]₂-Catalyzed Conjugate Addition of Arylboronic Acids to α,β-Unsaturated Ketones under Ligand-Free and Neutral Conditions
  作者：Lei Zhang、Xiaomin Xie、Lei Fu、Zhaoguo Zhang

  DOI：10.1021/jo4001367

  日期：2013.4.5

  A simple and efficient Ru-catalyzed conjugate addition reaction of arylboronic acids to α,β-unsaturated ketones under neutral conditions without any additional ligands has been developed. This Ru(II)-catalytic system both fulfilled the inhibition of the β-hydride elimination in the catalytic cycle and minimized the protonolysis of arylboronic acids.

  已开发出在中性条件下无需任何其他配体的简单有效的Ru催化的芳基硼酸与α，β-不饱和酮的Ru催化的共轭加成反应。该Ru（II）催化体系既实现了催化循环中对β-氢化物消除的抑制，又使芳基硼酸的质子分解最小化。
• Polymer-Supported Transition Metal Catalyst Complexes and Methods of Use
  申请人：Tunge Jon

  公开号：US20110230620A1

  公开（公告）日：2011-09-22

  A catalyst composition comprising a polymer functionalized with a ligand for binding a transition metal containing compound to form a transition metal complex, wherein said functionalized polymer has a number average molecular weight of about 5,000 to 30,000 g/mol and a polydispersity index of about 1.0 to 2.0. The catalyst is used in a hydroformylation reaction, preferably one in which the liquid phase has been volumetrically expanded with a compressed gas, is readily recyclable using nanofiltration.

  催化剂组成包括聚合物，其功能化以与过渡金属含配合物结合形成过渡金属配合物的配体。所述功能化聚合物的数量平均分子量约为5,000至30,000克/摩尔，聚分散指数约为1.0至2.0。该催化剂用于羰基化反应，最好是液相已经通过压缩气体体积膨胀，可以通过纳滤技术方便地回收利用。