2-(p-tolyl)propanenitrile | 75920-45-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(p-tolyl)propanenitrile
• 英文别名: 2-(4-methylphenyl)propionitrile；2-(4-methylphenyl)propanenitrile
• CAS: 75920-45-5
• 化学式: C₁₀H₁₁N
• mdl: MFCD11036541
• 分子量: 145.204
• InChiKey: VELPKXLIEFPYNV-UHFFFAOYSA-N

物化性质

• 沸点：
  80-90 °C(Press: 0.2 Torr)
• 密度：
  0.973±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 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：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(p-tolyl)propanenitrile 在 盐酸 、 氢溴酸 、 溴 作用下， 以 乙酸乙酯 为溶剂， 反应 3.0h， 生成 2-(4-溴甲基苯基)丙酸
  参考文献：
  名称：

  Design, synthesis, and evaluation of novel 2-phenylpropionic acid derivatives as dual COX inhibitory-antibacterial agents

  摘要：

  A series of 2-(4-substitutedmethylphenyl) propionic acid derivatives (6a-6m) were synthesized, characterized and evaluated for cyclooxygenase (COX) enzyme inhibitory and antimicrobial activity. Test compounds that exhibited good COX inhibition and antibacterial activity were further screened for their cytotoxicity and genotoxicity. Compounds 6h and 6l showed better COX-1 and COX-2 inhibition when compared to ibuprofen. Inhibition potency of these compounds against COX-2 was very close to that of nimesulide. The compounds 6d, 6h, 6l and 6m displayed promising antibacterial property when compared to chloramphenicol. However, the compound 6l was emerged as the best dual COX inhibitory-antibacterial agent in this study. The ADME prediction of the compounds revealed that they may have a good pharmacokinetic profile. Docking results of the compounds 6h and 6l with COX-1 (PDB ID: 1EQG) also exhibited a strong binding profile.

  DOI：

  10.1080/14756366.2017.1310726
• 作为产物：
  描述：

  1-(4-甲基苯基)-1-乙醇 在 3,6‐di‐tert‐butyl‐9‐mesityl‐10‐phenylacridin‐10‐ium tetrafluoroborate 、 碘 、 三溴化磷 、 magnesium 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 反应 27.0h， 生成 2-(p-tolyl)propanenitrile
  参考文献：
  名称：

  Csp3 处的三重选择性和顺序多样化：扩大烷基甲硼烷反应性以形成 C−C 和 C−杂原子键

  摘要：

  我们报道了携带 Cl、Bpin 和 GeEt 3的单个 C sp 3碳的三重选择性和顺序多样化，用于直接构建富含 sp 3的分子。烷基锗烷官能化的范围也在此得到显着扩展。

  DOI：

  10.1002/anie.202401545

文献信息

• Copper-Catalyzed Cyanation of <i>N</i>-Tosylhydrazones with Thiocyanate Salt as the “CN” Source
  作者：Yubing Huang、Yue Yu、Zhongzhi Zhu、Chuanle Zhu、Jinghe Cen、Xianwei Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1021/acs.joc.7b00836

  日期：2017.7.21

  A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.

  通过使用硫氰酸盐作为氰化物源的N-甲苯磺酰hydr的铜催化氰化反应，已成功实现了合成α-芳基腈的新方法。该方法的特点包括操作方便，易于获得的底物，低毒性的硫氰酸盐和广泛的底物范围。
• Synthesis of α-Aryl Nitriles through Palladium-Catalyzed Decarboxylative Coupling of Cyanoacetate Salts with Aryl Halides and Triflates
  作者：Rui Shang、Dong-Sheng Ji、Ling Chu、Yao Fu、Lei Liu

  DOI：10.1002/anie.201006763

  日期：2011.5.2

  Worth its salt: The palladium‐catalyzed decarboxylative coupling of the cyanoacetate salt as well as its mono‐ and disubstituted derivatives with aryl chlorides, bromides, and triflates is described (see scheme). This reaction is potentially useful for the preparation of a diverse array of α‐aryl nitriles and has good functional group tolerance. S‐Phos=2‐(2,6‐dimethoxybiphenyl)dicyclohexylphosphine)

  值得其盐：描述了氰基乙酸盐及其与芳基氯化物，溴化物和三氟甲磺酸酯的钯催化的脱羧偶联反应（参见方案）。该反应对于制备各种α-芳基腈具有潜在的实用性，并具有良好的官能团耐受性。S-Phos = 2-（（2,6-二甲氧基联苯）二环己基膦），Xant-Phos = 4,5-双（二苯基膦基）-9,9-二甲基x吨。
• Time Programmable Locking/Unlocking of the Calix[4]arene Scaffold by Means of Chemical Fuels
  作者：Daniele Del Giudice、Emanuele Spatola、Roberta Cacciapaglia、Alessandro Casnati、Laura Baldini、Gianfranco Ercolani、Stefano Di Stefano

  DOI：10.1002/chem.202002574

  日期：2020.11.20

  2‐cyano‐2‐phenylpropanoic acid and its p‐Cl, p‐CH3 and p‐OCH3 derivatives can be used as chemical fuels to control the geometry of the calix[4]arene scaffold in its cone conformation. It is shown that, under the action of the fuel, the cone calix[4]arene platform assumes a “locked” shape with two opposite aromatic rings strongly convergent and the other two strongly divergent (“pinched cone” conformation). Only when

  在这项工作中，我们报道了2-氰基-2-苯基丙酸和其p -Cl，p -CH 3和p -OCH 3衍生物可用作化学燃料，以控制其圆锥构象的杯[4]芳烃骨架的几何形状。结果表明，在燃料的作用下，圆锥杯[4]芳烃平台呈“锁定”形状，两个相对的芳环强烈会聚，另外两个强烈发散（“夹锥”构象）。仅当燃料耗尽时，圆锥杯[4]芳烃支架才会恢复其静止的“解锁”形状。值得注意的是，“锁定”状态的持续时间可以通过改变燃料结构或数量随意控制。该过程的动力学研究表明，燃料的消耗是由“解锁的”杯芳烃催化的，该杯芳烃充当其自身生产的自催化剂。提出了一种用于燃料消耗反应的机制。
• Atom-Economical and Tandem Conversion of Nitriles to <i>N</i>-Methylated Amides Using Methanol and Water
  作者：Bhaskar Paul、Milan Maji、Sabuj Kundu

  DOI：10.1021/acscatal.9b03916

  日期：2019.11.1

  A cobalt complex catalyzed tandem conversion of nitrile to N-methylated amide is described using a methanol and water mixture. Using this protocol, several nitriles were directly and efficiently converted to the desired N-methylated amides. Kinetic experiments using H2O18 and CD3OD suggested that water and methanol were the source of the oxygen atom and methyl group, respectively, in the final N-methylated

  描述了使用甲醇和水的混合物的钴络合物催化的腈串联转化为N-甲基化酰胺。使用该方案，将几个腈直接有效地转化为所需的N-甲基化酰胺。使用H 2 O 18和CD 3 OD进行的动力学实验表明，水和甲醇分别是最终N中氧原子和甲基的来源。-甲基化酰胺。重要的是，控制实验实现了活性Co（I）–H物种参与该转化的过程。动力学同位素效应（KIE）研究表明，甲醇C–H键的活化是动力学上重要的一步。哈米特图证实了电子不足的腈的反应更快。此外，计算研究支持了从腈形成N-甲基化酰胺的可能途径。
• Enantioselective hydrolysis of various racemic α-substituted arylacetonitriles using Rhodococcus sp. CGMCC 0497
  作者：Zhong-Liu Wu、Zu-Yi Li

  DOI：10.1016/s0957-4166(02)00017-4

  日期：2001.12

  The enantioselective hydrolysis of 17 racemic α-substituted arylacetonitriles by Rhodococcus sp. CGMCC 0497 is described. The corresponding (R)-amides and (S)-acids were obtained with excellent enantiomeric excess in most cases. The effect of steric and electronic factors on the outcome of the reactions are discussed here. The results prove that nitrile-converting enzymes are efficient tools for the

  Rhodococcus sp。对映体选择性水解17种外消旋的α-取代的芳基乙腈。描述了CGMCC 0497。在大多数情况下，以优异的对映体过量获得相应的（R）-酰胺和（S）-酸。此处讨论了空间和电子因素对反应结果的影响。结果证明腈转化酶是用于合成空间上不受阻碍的手性α-芳基丙酸和酰胺的有效工具。