N-phenethylcyclohexanecarboxamide | 53182-00-6

• 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: N-phenethylcyclohexanecarboxamide
• 英文别名: N-(2-phenylethyl)cyclohexanecarboxamide
• CAS: 53182-00-6
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: GPUHUEHNYUSRPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-phenethylcyclohexanecarboxamide 在 叔丁基过氧化氢 、 碘 作用下， 以 乙腈 为溶剂， 反应 36.0h， 以52%的产率得到2-cyclohexyl-5-phenyloxazole
  参考文献：
  名称：

  Iodine catalysed intramolecular C(sp³)–H functionalization: synthesis of 2,5-disubstituted oxazoles from N-arylethylamides

  摘要：

  碘催化合成2,5-取代噁唑，通过金属无催化条件下的分子内C(sp3)–H官能化，从N-芳基乙酰胺中进行描述。

  DOI：

  10.1039/c5ra13441b
• 作为产物：
  描述：

  环己甲醇 在 2,2,6,6-四甲基哌啶氧化物 、 三氯异氰尿酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 N-phenethylcyclohexanecarboxamide
  参考文献：
  名称：

  TEMPO-Catalyzed Oxidative Amidation of Alcohols via Hexa­fluoroisopropyl Esters

  摘要：

  Stepwise oxidative amidation of alcohols using trichloroisocyanuric acid, a catalytic amount of TEMPO in combination with pyridine and hexafluoroisopropyl (HFIP) alcohol followed by amines is described. This procedure used HFIP esters as activating esters which were found to be very efficient acylating agents for amide bond formation. This process is compatible with a number of functional groups and acid-sensitive protecting groups.

  DOI：

  10.1055/s-0034-1381056

文献信息

• A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines
  作者：Hieu-Trinh Luu、Stefan Wiesler、Georg Frey、Jan Streuff

  DOI：10.1021/acs.orglett.5b00987

  日期：2015.5.15

  presented that gives direct access to 1,1-disubstituted tetrahydroisoquinolines. The reaction is a titanium(III)-catalyzed reductive umpolung process in which nitriles act as effective acylation agents. The method is highly chemo- and regioselective and is demonstrated in 20 examples. It is well-suited for the large-scale synthesis of functionalized tetrahydroisoquinoline products, which is exemplified in

  提出了3，4-二氢异喹啉的催化还原性C 1酰化，其可直接获得1，1-二取代的四氢异喹啉。该反应是钛（III）催化的还原性物质化工艺，其中腈充当有效的酰化剂。该方法具有高度的化学选择性和区域选择性，并在20个实例中得到了证明。它非常适合大规模合成官能化的四氢异喹啉产物，以（±）-3-脱甲氧基赤藓醇二酮的六步合成形式例举。
• Synthesis of Aliphatic Amides through a Photoredox Catalyzed Radical Carbonylation Involving Organosilicates as Alkyl Radical Precursors
  作者：Alex Cartier、Etienne Levernier、Anne‐Lise Dhimane、Takahide Fukuyama、Cyril Ollivier、Ilhyong Ryu、Louis Fensterbank

  DOI：10.1002/adsc.202000314

  日期：2020.5.26

  Alkyl radicals, from primary to tertiary, formed by photocatalyzed oxidation of organosilicates, are involved efficiently in radical carbonylation with carbon monoxide (CO), in the presence of various amines and CCl4, leading to a variety of amides in moderate to good yields.

  在各种胺和CCl 4的存在下，通过有机硅酸盐的光催化氧化形成的伯基到伯基的烷基有效地参与一氧化碳（CO）的自由基羰基化反应，从而以中等至良好的收率生成了各种酰胺。
• Phencyclidine-like effects of tetrahydroisoquinolines and related compounds
  作者：Nancy M. Gray、Brian K. Cheng、Stephen J. Mick、Cecelia M. Lair、Patricia C. Contreras

  DOI：10.1021/jm00126a016

  日期：1989.6

  3-c]pyridines, and related compounds were evaluated for their ability to inhibit binding of [3H]-1-[1-(2-thienyl)piperidine and [3H]-N-allylnormetazocine to phencyclidine (PCP) and sigma receptors, respectively. A representative series of compounds was evaluated in behavioral assays to determine the ability of the compounds to induce PCP-like stereotyped behavior and ataxia. All of the compounds caused stereotyped

  评价了一系列1,2,3,4-四氢异喹啉，四氢噻吩并[2,3-c]吡啶和相关化合物抑制[3H] -1- [1-（2-噻吩基）哌啶结合的能力和[3H] -N-烯丙基谷氨酸对苯环利定（PCP）和sigma受体的影响。在行为测定中评估了一系列代表性化合物，以确定这些化合物诱导PCP样​​定型行为和共济失调的能力。所有这些化合物均引起定型行为和共济失调，表明它们在PCP部位具有激动作用。
• Mild and Low-Pressure<i>fac</i>-Ir(ppy)₃-Mediated Radical Aminocarbonylation of Unactivated Alkyl Iodides through Visible-Light Photoredox Catalysis
  作者：Shiao Y. Chow、Marc Y. Stevens、Linda Åkerbladh、Sara Bergman、Luke R. Odell

  DOI：10.1002/chem.201601694

  日期：2016.6.27

  unactivated alkyl iodides employing a fac‐Ir(ppy)3‐catalyzed radical aminocarbonylation protocol has been developed. Using a two‐chambered system, alkyl iodides, fac‐Ir(ppy)3, amines, reductants, and CO gas (released ex situ from Mo(CO)6), were combined and subjected to an initial radical reductive dehalogenation generating alkyl radicals, and a subsequent aminocarbonylation with amines affording a

  已经开发出一种新颖，温和且简便的方法，可以通过未活化的烷基碘使用fac- Ir（ppy）3催化的自由基氨基羰基化方法制备烷基酰胺。使用两腔系统，将烷基碘，fac- Ir（ppy）3，胺，还原剂和CO气体（从Mo（CO）6异位释放）合并，并进行初始自由基还原性脱卤，生成烷基自由基，然后用胺进行氨基羰基化，以中等到极好的收率提供了广泛的烷基酰胺。
• Direct Amidation of Carboxylic Acids through an Active α-Acyl Enol Ester Intermediate
  作者：Xianjun Xu、Huangdi Feng、Liliang Huang、Xiaohui Liu

  DOI：10.1021/acs.joc.8b00819

  日期：2018.8.3

  The development of a highly efficient and simple protocol for the direct amidation of carboxylic acids is described employing ynoates as novel coupling reagents. The transformation proceeds in good to excellent yields via in situ α-acyl enol ester intermediates formation under mild reaction conditions. This useful method has been demonstrated for a range of substrates to provide a succinct access to

  描述了使用壬酸酯作为新型偶联剂来开发用于羧酸的直接酰胺化的高效且简单的方案。通过在温和的反应条件下原位形成α-酰基烯醇酯中间体，可将转化率以良好至极好的收率进行。已经证明了这种有用的方法可用于多种底物，以提供对结构多样的酰胺的简洁访问，包括格列本脲，替阿必利盐酸盐和那格列奈的关键中间体，并且可以以摩尔规模进行。