2-phenoxy-1-(piperidin-1-yl)ethanone | 36405-75-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-phenoxy-1-(piperidin-1-yl)ethanone
• 英文别名: 1-(Phenoxyacetyl)piperidine；2-phenoxy-1-piperidin-1-ylethanone
• CAS: 36405-75-1
• 化学式: C₁₃H₁₇NO₂
• mdl: MFCD00977650
• 分子量: 219.283
• InChiKey: IUPQNTVJUFOXAX-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±25.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-phenoxy-1-(piperidin-1-yl)ethanone 在 tetraphosphorus decasulfide 作用下， 以85.9%的产率得到phenoxythioacetopiperidide
  参考文献：
  名称：

  Kuliev, A. V.; Abdullaeva, M. I.; Akhadov, N. O., Journal of applied chemistry of the USSR, 1989, vol. 62, p. 1783 - 1786

  摘要：

  DOI：
• 作为产物：
  描述：

  苯氧乙酸 在 morpholinomethyl polystyrene HL 、 PS-Ph₃P resin 、 三氯乙腈 作用下， 以 二氯甲烷 为溶剂， 生成 2-phenoxy-1-(piperidin-1-yl)ethanone
  参考文献：
  名称：

  EFFICIENT PROCEDURE FOR THE PREPARATION OF AMIDES USING POLYMER-BOUND REAGENTS

  摘要：

  An effective method for the conversion of acids into amides is presented. The two-step procedure includes the preparation of acid chloride intermediates using Pol-Ph3P and subsequent treatment of these intermediates with amines and polymer-bound base. The amides were accessible in high yields and purities without further purification.

  DOI：

  10.1081/scc-100103528

文献信息

• Highly Enantioselective Hydrogenation of Amides via Dynamic Kinetic Resolution Under Low Pressure and Room Temperature
  作者：Loorthuraja Rasu、Jeremy M. John、Elanna Stephenson、Riley Endean、Suneth Kalapugama、Roxanne Clément、Steven H. Bergens

  DOI：10.1021/jacs.6b12254

  日期：2017.3.1

  High-throughput screening and lab-scale optimization were combined to develop the catalytic system trans-RuCl2((S,S)-skewphos)((R,R)-dpen), 2-PrONa, and 2-PrOH. This system hydrogenates functionalized α-phenoxy and related amides at room temperature under 4 atm H2 pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.

  高通量筛选和实验室规模优化相结合，开发了催化系统 trans-RuCl2((S,S)-skewphos)((R,R)-dpen)、2-PrONa 和 2-PrOH。该系统在室温和 4 个大气压的 H2 压力下氢化功能化的 α-苯氧基和相关酰胺，通过动态动力学拆分以高达 99% 的产率和大于 99% 的对映体过量得到手性醇。
• Solvent-Free Iron(III) Chloride-Catalyzed Direct Amidation of Esters
  作者：Blessing D. Mkhonazi、Malibongwe Shandu、Ronewa Tshinavhe、Sandile B. Simelane、Paseka T. Moshapo

  DOI：10.3390/molecules25051040

  日期：——

  work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%.

  酰胺官能团在具有多种有益应用的广泛有机化合物中很突出。在这项工作中，我们报告了通过氯化铁 (iii) 催化的酯直接酰胺化合成这些官能团。该反应在无溶剂条件下进行，发现与一系列胺和酯底物相容，可在较短的反应时间内生成所需的酰胺，并且在 15 mol% 的催化剂负载量下产率良好至极好。
• Synthesis and vasodilatory activity of some amide derivatives of 6-(4-carboxymethyloxyphenyl)-4,5-dihydro-3(2H)-pyridazinone
  作者：Ranju Bansal、Dinesh Kumar、Rosalia Carron、Carmen de la Calle

  DOI：10.1016/j.ejmech.2009.06.006

  日期：2009.11

  vasodilatory activity of some amide derivatives of 6-(4-carboxymethyloxyphenyl)-4,5-dihydro-3(2H)-pyridazinone are reported. An effect of substitution at 2-position of pyridazinone ring on vasodilatory potential has also been explored. The most active compound 6-[4-(2-oxo-2-pyrrolidin-1-yl-ethoxy)phenyl]-2-(4-fluorophenyl)-4,5-dihydropyridazin-3(2H)-one (11) exhibited vasodilating activity in nanomolar

  报道了6-（4-羧甲基氧苯基）-4，5-二氢-3（2H）-哒嗪酮的一些酰胺衍生物的合成和血管舒张活性。还研究了哒嗪酮环的2-位取代对血管舒张电位的影响。活性最高的化合物6- [4-（2-氧代-2-吡咯烷-1-基-乙氧基）苯基] -2-（4-氟苯基）-4,5-二氢哒嗪-3（2 H）-一（11）在纳摩尔范围内（IC 50  = 0.051μM ）表现出血管舒张活性。
• THERAPEUTIC COMPOSITIONS AND RELATED METHODS OF USE
  申请人：Salituro Francesco G.

  公开号：US20120165324A1

  公开（公告）日：2012-06-28

  Compositions comprising compounds that modulate pyruvate kinase M2 (PKM2) are described herein. Also described herein are methods of using the compounds that modulate PKM2 in the treatment of cancer.

  本文介绍了包含调节丙酮酸激酶M2（PKM2）的化合物的组合物。本文还介绍了使用调节PKM2的化合物治疗癌症的方法。
• Catalytic Reductive Dehydration of Tertiary Amides to Enamines under Hydrosilylation Conditions
  作者：Alexey Volkov、Fredrik Tinnis、Hans Adolfsson

  DOI：10.1021/ol403302g

  日期：2014.2.7

  Tertiary amides are efficiently reduced to their corresponding enamines under hydrosilylation conditions, using a transition-metal-free catalytic protocol based on t-BuOK (5 mol %) and (MeO)(3)SiH or (EtO)(3)SiH as the reducing agent. The enamines were formed with high selectivity in good-to-excellent yields.