4-oxo-n-pentano-p-toluidide | 84417-34-5

• 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: 4-oxo-n-pentano-p-toluidide
• 英文别名: N-(p-tolyl)-4-oxopentamide；levulinic acid p-toluidide；Laevulinsaeure-p-toluidid；α-acetonyl-p-acetotoluidide；N-(4-methylphenyl)-4-oxopentanamide
• CAS: 84417-34-5
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: FPYXCYVYXOPHOO-UHFFFAOYSA-N

物化性质

• 熔点：
  103-104 °C
• 沸点：
  400.1±28.0 °C(Predicted)
• 密度：
  1.106±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-oxo-n-pentano-p-toluidide 在 ketoreductase P₁-A₀₄ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 异丙醇 为溶剂， 以99%的产率得到
  参考文献：
  名称：

  在水介质中金属催化的环化和生物催化的组合：手性醇，内酯和γ-羟基-羰基化合物的不对称结构

  摘要：

  在水性介质中金属链催化的含链状亲核试剂作为取代基的炔烃的环异构化（随后是瞬时形成的五元杂环的自发水解，加氢烷氧基化或氨解）与随后的对映选择性酮生物还原（由KRED介导）已经实现。正式涉及三步一锅反应的整个转化过程提供了各种对映纯有价值的分子（例如1,4-二醇，内酯和γ-羟基羰基化合物（羧酸，酯和酰胺） ）具有较高的转化率和对映选择性，并且在温和的反应条件下，公开了炔烃在水中金属催化的环异构化和酶催化的集成化概念。

  DOI：

  10.1021/acscatal.7b02183
• 作为产物：
  描述：

  当归内酯 、 乙烷,三氯氟- 生成 4-oxo-n-pentano-p-toluidide
  参考文献：
  名称：

  Security rethink

  摘要：

  Michael Chua 表示，如果我们有机会重新考虑我们的信息安全策略，我们就不太可能继续采用当前的做法，他认为全面的方法会带来意想不到的副作用

  DOI：

  10.1093/combul/44.5.22

文献信息

• Conjugates of catecholamines. 1. N-Alkyl-functionalized carboxylic acid congeners and amides related to isoproterenol
  作者：Kenneth A. Jacobson、Debra Marr-Leisy、Roberto P. Rosenkranz、Michael S. Verlander、Kenneth L. Melmon、Murray Goodman

  DOI：10.1021/jm00358a007

  日期：1983.4

  substituted amide. The compounds were prepared generally via the reductive amination of norepinephrine with a keto acid or a preformed keto amide. An alternate synthesis of the model amide derivatives, involving activation of the carboxylic acid congeners and coupling with amines, was complicated in the case of short-chain derivatives by facile cyclization to lactams. In vitro evaluation of these compounds

  合成了一系列官能化的儿茶酚胺（同类物），其中形式上，异丙肾上腺素的N-异丙基已被长度可变的直链烷基链延长，并被羧基或取代的酰胺封端。通常通过将去甲肾上腺素与酮酸或预先形成的酮酰胺还原胺化来制备化合物。在短链衍生物的情况下，通过酰胺环容易地环合成内酰胺，模型酰胺衍生物的替代合成涉及羧酸同系物的活化和与胺的偶合。这些化合物作为潜在的β-肾上腺素能激动剂的体外评估表明，尽管羧酸同类物的功效相对较低，模型酰胺衍生物的效力高度依赖于烷基链的长度以及酰胺上取代基的性质。通常，芳族酰胺是最有效的，尽管芳族基团上取代基的性质和位置会极大地影响其效力。讨论了这些研究的意义，包括一般的β-肾上腺素药物设计以及羧酸同类物与载体的连接。
• Pharmacologically active compounds
  申请人：Allen & Hanburys Limited

  公开号：US04000193A1

  公开（公告）日：1976-12-28

  Compounds of the formula: ##STR1## in which: R.sub.4 and R.sub.5 independently represent hydrogen or lowr alkyl; R.sub.6 represents a straight or branched alkyl or alkenyl group containing from 4 to 6 carbon atoms, inclusive, or R.sub.6 represents a straight or branched alkyl group containing from 2 to 6 carbon atoms, inclusive, which alkyl group is substituted by one or more hydroxy, alkoxy or acyloxy groups; or by an aryl group which may be substituted by one or more hydroxy, alkoxy or acyloxy groups as before; and R.sub.7 represents a straight or branched alkyl group containing from 3 to 6 carbon atoms, inclusive, optionally substituted by an alkoxy group or by an aryl or aryloxy group which, alkoxy, aryl or aryloxy group may, in turn be substituted by hydroxy, alkoxy, acetamido or methanesulphonamido groups, And pharmaceutically acceptable salts thereof. These compounds have utility in the treatment of cardiovascular diseases.

  该公式化合物的化合物：##STR1##其中：R.sub.4和R.sub.5分别代表氢或低碳烷基；R.sub.6代表含有4到6个碳原子的直链或支链烷基或烯基基团，或者R.sub.6代表含有2到6个碳原子的直链或支链烷基基团，该烷基基团被一个或多个羟基、烷氧基或酰氧基取代；或者由一个芳基代表，该芳基可以被一个或多个羟基、烷氧基或酰氧基取代，R.sub.7代表含有3到6个碳原子的直链或支链烷基基团，可选择地被烷氧基取代或由芳基或芳基氧基基团取代，该烷氧基、芳基或芳基氧基基团，依次可以被羟基、烷氧基、乙酰胺基或甲磺酰胺基基团取代。及其药学上可接受的盐。这些化合物在心血管疾病的治疗中具有用途。
• Highly Efficient and Versatile Synthesis of Lactams and <i>N</i>-Heterocycles via Al(OTf)₃-Catalyzed Cascade Cyclization and Ionic Hydrogenation Reactions
  作者：Jianguo Qi、Chenbin Sun、Yulin Tian、Xiaojian Wang、Gang Li、Qiong Xiao、Dali Yin

  DOI：10.1021/ol403173x

  日期：2014.1.3

  The discovery and development of an efficient and versatile method for the synthesis of N-substituted lactams is described. Pyrrolindinones, piperidones, and structurally related heterocycles were formed by Al(OTf)3-catalyzed cascade cyclization and ionic hydrogenation reactions of corresponding nitrogen substituted ketoamides in good yields.

  描述了用于合成N-取代的内酰胺的有效且通用的方法的发现和发展。通过Al（OTf）3催化的级联环化反应和相应的氮取代酮酰胺的离子加氢反应以高收率形成吡咯烷二酮，哌啶酮和与结构相关的杂环。
• Congener derivatives and conjugates of histamine: synthesis and tissue and receptor selectivity of the derivatives
  作者：M. M. Khan、K. L. Melmon、D. Marr-Leisy、M. S. Verlander、M. Egli、S. Lok、M. Goodman

  DOI：10.1021/jm00394a031

  日期：1987.11

  A series of 19 congener derivatives and conjugates of histamine was synthesized and tested to determine whether the ligands would alter the conventional histamine activity in various tissues. The derivatives, which contained either branched or unbranched aliphatic groups, aromatic amide groups, or dipeptides, exhibited affinities for histamine type 1 and/or type 2 receptors that were widely different from the progenitor. The p-trifluoromethyl derivative of histamine with an intermediate chain length of four methylenes (compound 13) was the most potent lymphocytes H2 receptor agonist but was inactive on guinea pig myocardium H2 receptors. The deletion of a single methylene chain (compound 12) from this compound resulted in total loss of its H2 activity on lymphocytes and its H1 activity on aorta. Compound 12 became an exclusive H1 agonist on lymphocytes H1 receptors. The dipeptide conjugate (compound 17) and the aliphatic congener derivative (compound 18), both with four methylenes, retained some of the activity on guinea pig myocardium H2 receptors, but lost their activity on lymphocytes H2 receptors. Therefore, histamine can be modified at sites that are at a distance from the imidazole moiety, resulting in tissue selective histamine receptor agonists.
• Subbaraj, A.; Ramakrishnan, V. T., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, # 6, p. 506 - 513
  作者：Subbaraj, A.、Ramakrishnan, V. T.

  DOI：——

  日期：——