4-(4-methylbenzyl)benzonitrile | 71947-05-2

• 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-(4-methylbenzyl)benzonitrile
• 英文别名: 4-[(4-methylphenyl)methyl]benzonitrile
• CAS: 71947-05-2
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: YUKIURCFPBCBJW-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  350.7±21.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  4-(4-methylbenzyl)benzonitrile 在 lithium aluminium tetrahydride 、 N-羟基-7-氮杂苯并三氮唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 4-chloro-3-ethyl-1-methyl-N-(4-(4-methylbenzyl)benzyl)-1H-pyrazole-5-carboxamide
  参考文献：
  名称：

  Structure–Activity Relationship Studies of Tolfenpyrad Reveal Subnanomolar Inhibitors ofHaemonchus contortusDevelopment

  摘要：

  Recently, we have discovered that the registered pesticide, tolfenpyrad, unexpectedly and potently inhibits the development of the L4 larval stage of the parasitic nematode Haemonchus contortus with an IC50 value of 0.03 mu M while displaying good selectivity, with an IC50 of 37.9 mu M for cytotoxicity. As a promising molecular template for medicinal chemistry optimization, we undertook anthelmintic structure-activity relationships for this chemical. Modifications of the left-hand side (LHS), right-hand side (RHS), and middle section of the scaffold were explored to produce a set of 57 analogues. Analogues 25, 29, and 33 were shown to be the most potent compounds of the series, with IC50 values at a subnanomolar level of potency against the chemotherapeutically relevant fourth larval (L4) stage of H. contortus. Selected compounds from the series also showed promising activity against a panel of other different parasitic nematodes, such as hookworms and whipworms.

  DOI：

  10.1021/acs.jmedchem.8b01789
• 作为产物：
  描述：

  对甲苯基氯化镁 在 [Fe(bis(diphenylphosphino)ethane)2(MeCN)2][(BF₄)2] 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 4-(4-methylbenzyl)benzonitrile
  参考文献：
  名称：

  简化铁膦催化剂的交叉偶联反应

  摘要：

  有旧铁吗？以前，基于二膦配体双（二苯基膦基）乙烷的铁催化剂在铁催化的交叉偶联过程中表现不佳。然而，事实证明，这并不是由于与配体有关的固有性能较差，而是由于在形成活性Fe I物种之前或之中需要形成双螯合物。

  DOI：

  10.1002/anie.201207868

文献信息

• A SO2F2 mediated mild, practical, and gram-scale dehydroxylative transforming primary alcohols to quaternary ammonium salts
  作者：Chuang Zhao、Gao-Feng Zha、Wan-Yin Fang、Njud S. Alharbi、Hua-Li Qin

  DOI：10.1016/j.tet.2019.07.007

  日期：2019.8

  A simple, practical and gram-scale process for direct transformation of primary alcohols or silyl ethers to ammonium salts was developed. This method has the feathers of easy work-up (a simple filtration), mild condition, high yield, great practicality and robustness. And the application of the ammonium salts in Suzuki coupling reaction was also accomplished.

  开发了一种简单，实用和克级的方法，用于将伯醇或甲硅烷基醚直接转化为铵盐。该方法具有易于处理（过滤简单），条件温和，收率高，实用性强和耐用性强的特点。并完成了铵盐在铃木偶联反应中的应用。
• Construction of Di(hetero)arylmethanes Through Pd-Catalyzed Direct Dehydroxylative Cross-Coupling of Benzylic Alcohols and Aryl Boronic Acids Mediated by Sulfuryl Fluoride (SO₂ F₂ )
  作者：Chuang Zhao、Gao-Feng Zha、Wan-Yin Fang、K. P. Rakesh、Hua-Li Qin

  DOI：10.1002/ejoc.201801888

  日期：2019.2.28

  A practical Pd‐catalyzed direct dehydroxylative coupling of (hetero)benzylic alcohols with (hetero)arylboronic acids for the constructions of di(hetero)arylmethane derivatives under SO2F2 was described. This new method provided a strategically distinct approach to di(hetero)arylmethane derivatives from readily available and abundant benzylic alcohols under mild condition.

  描述了一种实用的Pd催化的（杂）苄醇与（杂）芳基硼酸的直接脱羟基偶联，用于在SO 2 F 2下构造二（杂）芳基甲烷衍生物。这种新方法在温和的条件下提供了一种战略上独特的方法，用于从易得的和丰富的苄醇中制取二（杂）芳基甲烷衍生物。
• Cucurbit[7]uril promoting PdCl2-catalyzed cross-coupling reaction of benzyl halides and arylboronic acids in aqueous media
  作者：Guangkuan Zhao、Zhen Wang、Ruixin Wang、Jingya Li、Dapeng Zou、Yangjie Wu

  DOI：10.1016/j.tetlet.2014.07.060

  日期：2014.9

  The research provides a novel approach for producing diarylmethane derivatives using CB[7]–NaCl–PdCl2 catalyzed Suzuki cross-coupling reaction of benzyl chloride derivatives and arylboronic acids in ethanol aqueous solution.

  该研究提供了一种新方法，可在乙醇水溶液中使用CB [7] -NaCl-PdCl 2催化苄基氯衍生物与芳基硼酸的Suzuki交叉偶联反应生产二芳基甲烷衍生物。
• Dual copper- and photoredox-catalysed C(sp²)–C(sp³) coupling
  作者：Euan B. McLean、Vincent Gauchot、Sebastian Brunen、David J. Burns、Ai-Lan Lee

  DOI：10.1039/c9cc01718f

  日期：——

  The use of copper catalysis with visible light photoredox catalysis in a cooperative fashion has recently emerged as a versatile means of developing new C–C bond forming reactions. In this work, dual copper and photoredox catalysis is exploited to effect C(sp2)–C(sp3) cross-couplings between aryl boronic acids and benzyl bromides.

  铜催化与可见光光氧化还原催化以合作方式的结合最近已成为开发新型C–C键形成反应的通用手段。在这项工作中，利用铜和光氧化还原双重催化作用来实现芳基硼酸和苄基溴之间的C（sp 2）–C（sp 3）交叉偶联。
• Efficient synthesis of diarylmethane derivatives by PdCl 2 catalyzed cross-coupling reactions of benzyl chlorides with aryl boronic acids in aqueous medium
  作者：Guangkuan Zhao、Kena Zhang、Liang Wang、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1016/j.tetlet.2015.10.053

  日期：2015.12

  The research provides a simple and efficient method for preparing diarylmethane derivatives using the cross-coupling reaction of benzyl chlorides and aryl boronic acids catalyzed by palladium chloride in DMF aqueous solution without additional ligand.

  该研究提供了一种简单而有效的方法，该方法使用氯化钯在DMF水溶液中催化的苄基氯和芳基硼酸的交叉偶联反应制备苄基氯和芳基硼酸，而无需其他配体。