4-(2-hydroxypropan-2-yl)benzonitrile | 77802-22-3

• 物质功能分类: 有机原料 - 腈类化合物
• 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-(2-hydroxypropan-2-yl)benzonitrile
• 英文别名: 2-(4-cyanophenyl)-2-propanol；4-(1-hydroxy-1-methyl-ethyl)-benzonitrile
• CAS: 77802-22-3
• 化学式: C₁₀H₁₁NO
• 分子量: 161.203
• InChiKey: FJDCEKDPEOIGEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  49-51 °C
• 沸点：
  299.0±23.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(2-hydroxypropan-2-yl)benzonitrile 在 bismuth(lll) trifluoromethanesulfonate 、 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 水 为溶剂， 反应 36.0h， 以85%的产率得到对氰基苯乙酮
  参考文献：
  名称：

  叔芳香醇在水中被氧化成酮

  摘要：

  一种新的基于松香的两亲物能够在温和条件下氧化水中的芳族叔醇。氧化过程是由烷氧基的β断裂介导的。我们的催化剂体系，包括表面活性剂，催化剂和水，可以在同一反应瓶中轻松回收。

  DOI：

  10.1002/adsc.201800612
• 作为产物：
  描述：

  4-异丙基苯甲腈 在 cis-RuCl₂(4,4'-di-tert-butyl-2,2'-bipyridine)2 、 溶剂黄146 、 高碘酸 作用下， 以 水 为溶剂， 反应 4.03h， 以90%的产率得到4-(2-hydroxypropan-2-yl)benzonitrile
  参考文献：
  名称：

  酸中钌催化的 C-H 羟基化使胺衍生物的选择性官能化成为可能

  摘要：

  描述了用于 sp3 CH 羟基化的新催化协议的识别、优化和评估。反应在酸水溶液中使用双（联吡啶）Ru 催化剂进行，以氧化具有碱性胺官​​能团的底物。对于许多胺衍生物，叔和苄基 CH 羟基化比 N-氧化更受青睐。对于萜烯衍生的底物，观察到对叔和苄基 CH 键的反应性的类似趋势。尽管反应介质具有电离强度，但手性三级中心的羟基化是对映特异性的。初步动力学实验显示异构顺式和反式 Ru 催化剂之间的反应性存在显着差异，表明该催化剂在反应条件下构型稳定。

  DOI：

  10.1021/jacs.7b05469

文献信息

• The chemoselective reduction of nitro compounds: scope of the electrochemical method
  作者：JM Chapuzet、R Labrecque、M Lavoie、E Martel、J Lessard

  DOI：10.1051/jcp/1996930601

  日期：——

  The selective electrohydrogenation of nitro aliphatic and nitro aromatic functional groups in molecules containing other groups that are easy to hydrogenate (activated double bond, carbon-iodine bond, nitrile,) has been sucessfully carried out in slightly acidic (pH = 3) or neutral (pH = 5-6) methanol-water solutions at Devarda copper and Raney cobalt electrodes. The electrochemical synthesis of a quinolone 15 and a quinoxaline 18 is also reported. Preliminary results on the preparative electroreduction of 5-nitroindole 21 on Hg in aqueous methanol with HBr as supporting electrolyte are presented and dicussed for the first time.

  在含有其他易氢化基团（活化双键、碳-碘键、氰基）的分子中，对硝基脂肪族和硝基芳香族官能团的选择性电氢化已在微酸性（pH = 3）或中性（pH = 5-6）的甲醇-水溶液中，在德尔瓦铜和拉尼钴电极上成功进行。本文还报道了喹诺酮15和喹喉18的电化学合成。首次介绍了在含氢溴酸的甲醇水溶液中，在汞上进行5-硝基吲哚21的制备电还原的初步结果，并进行了讨论。
• Kinetics and Mechanism of Acid Catalysed Hydration of α-Methylstyrenes
  作者：Oldřich Pytela、Bronislav Trlida

  DOI：10.1135/cccc20071025

  日期：——

  Twelve para-substituted α-methylstyrenes with substituents H, CH₃, CF₃, CH₃O, CH₃S, F, Cl, Br, CH₃CO, CH₃SO₂, CN a NO₂ were synthesised; additionally, the acid catalysed hydration kinetics of these compounds were measured in sulfuric acid in a concentration range c from 0.017 to 9.58 mol l^-1, at 25.0 °C. The observed rate constants obtained were used to construct the kinetic acidity function and calculate the catalytic rate constants. Based on the evaluation of the acidity function kinetic dependence on acid medium concentration, and the substituent effects of acid catalysed hydration of α-methylstyrenes on the catalytic rate constants, the mechanism of acid catalysed hydration was verified. The mechanism involves the addition of a proton to the double bond of α-methylstyrene in the rate-limiting reaction step denoted as A-SE2. No evident difference was found between the effects of the acid medium on the acid catalysed hydration of styrenes and α-methylstyrenes, which indicates very similar activity coefficients of the reactants, and of the transition state of both substrates. The substituent effects evaluation shows that the rate-limiting step of the reaction consists in the addition of a proton to the substrate. The carbocation formation in the transition state of this reaction step proceeds roughly half-way compared with the extent of the carbocation formation by cumyl chloride hydrolysis. The obtained carbocation is in particular stabilised by the substituents with +M effect, while the influence of the substituents with -M and I effects is significantly smaller.

  十二种带有取代基H、CH₃、CF₃、CH₃O、CH₃S、F、Cl、Br、CH₃CO、CH₃SO₂、CN和NO₂的α-甲基苯乙烯被合成；此外，在浓度范围从0.017到9.58摩尔/升的硫酸中，测量了这些化合物的酸催化水合动力学。所得到的观察速率常数被用来构建动力学酸度函数并计算催化速率常数。通过评估酸性函数动力学对酸性介质浓度的依赖性，以及α-甲基苯乙烯的酸催化水合反应的取代基效应对催化速率常数的影响，验证了酸催化水合的机理。该机理涉及在速率限制的反应步骤中向α-甲基苯乙烯的双键加入质子，被标记为A-SE2。在酸性介质对苯乙烯和α-甲基苯乙烯的酸催化水合的影响之间没有明显差异，这表明反应物和两种底物的过渡态的活性系数非常相似。取代基效应评估显示，反应的速率限制步骤在向底物加入质子时发生。与叔丁基氯化物水解形成的碳正离子相比，该反应步骤的过渡态中的碳正离子形成大致进行了一半。所得到的碳正离子特别受到具有+M效应的取代基的稳定作用，而具有-M和I效应的取代基的影响则明显较小。
• Development of a Synthesis of a 2,3-Disubstituted 4,7-Diazaindole Including Large-Scale Application of CH₃Li/TiCl₄-Mediated Methylation of an Enolizable Ketone
  作者：Franz J. Weiberth、Harpal S. Gill、George E. Lee、Duc P. Ngo、Frederick L. Shrimp、Xuemin Chen、Geoffrey D’Netto、Bryan R. Jackson、Ying Jiang、Narendra Kumar、Frederick Roberts、Evgeny Zlotnikov

  DOI：10.1021/op5003769

  日期：2015.7.17

  The chemical development of a 2,3-disubstituted 4,7-diazaindole is described. The requisite tertiary carbinol substrate was prepared employing in situ-generated CH3TiCl3 as a chemoselective and preferred reagent compared to CH3MgX for methyl addition to an enolizable ketone. The 4,7-diazaindole ring system was efficiently assembled via an intramolecular Chichibabin transformation. The optimized processes

  描述了2，3-二取代的4，7-二氮吲哚的化学显影。与将CH 3 MgX用于将甲基加成到可烯醇化的酮中相比，使用原位生成的CH 3 TiCl 3作为化学选择性和优选的试剂制备必需的叔甲醇底物。通过分子内Chichibabin转化有效地组装了4，7-二氮吲哚环系统。优化的过程在中试规模上进行，以提供千克量的目标分子。
• HETEROAROMATIC COMPOUNDS FOR USE AS HIF INHIBITORS
  申请人：Härter Michael

  公开号：US20110301122A1

  公开（公告）日：2011-12-08

  The present application relates to novel substituted aryl compounds, processes for their preparation, their use for treatment and/or prevention of diseases and their use for the preparation of medicaments for treatment and/or prevention of diseases, in particular for treatment and/or prevention of hyperproliferative and angiogenic diseases and those diseases which arise from metabolic adaptation to hypoxic states. Such treatments can be carried out as monotherapy or also in combination with other medicaments or further therapeutic measures.

  本申请涉及新型取代芳基化合物，其制备方法，它们用于治疗和/或预防疾病以及用于制备治疗和/或预防疾病的药物，特别是用于治疗和/或预防过度增殖和血管生成性疾病以及那些由于代谢适应缺氧状态而引起的疾病。这种治疗可以作为单独治疗进行，也可以与其他药物或进一步的治疗措施结合使用。
• Aryl compounds with aminoalkyl substituents and their use
  申请人：Härter Michael

  公开号：US20110312930A1

  公开（公告）日：2011-12-22

  The present application relates to novel aryl compounds with aminoalkyl substituents, to processes for their preparation, to their use for treatment and/or prevention of diseases and to their use for the preparation of medicaments for treatment and/or prevention of diseases, in particular for treatment and/or prevention of hyperproliferative and angiogenic diseases and those diseases which arise from metabolic adaptation to hypoxic states. Such treatments can be carried out as monotherapy or also in combination with other medicaments or further therapeutic measures.

  本申请涉及具有氨基烷基取代基的新型芳基化合物，涉及其制备方法，涉及它们用于治疗和/或预防疾病以及用于制备治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防过度增殖和血管生成性疾病以及那些由于代谢适应低氧状态而引起的疾病。这种治疗可以作为单独治疗进行，也可以与其他药物或进一步的治疗措施结合使用。