1-[(3-甲基苯基)甲基]萘 | 184587-47-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-[(3-甲基苯基)甲基]萘
• 英文名称: 1-(3-Methyl-benzyl)-naphthalene
• 英文别名: Naphthalene, 1-[(3-methylphenyl)methyl]-；1-[(3-methylphenyl)methyl]naphthalene
• CAS: 184587-47-1
• 化学式: C₁₈H₁₆
• 分子量: 232.325
• InChiKey: DGGYVOUQJHUEIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  萘 、 3-甲基苄基氯 在 三氯化铝 作用下， 以 硝基甲烷 为溶剂， 反应 0.03h， 以62%的产率得到1-[(3-甲基苯基)甲基]萘
  参考文献：
  名称：

  使用微波的 FRIEDEL-CRAFTS 萘反应的硝基甲烷引发剂

  摘要：

  使用卤素衍生物对萘进行烷基化可以在非常简单的条件下通过 Friedel-Crafts 反应实现。通过对含有反应混合物和少量硝基甲烷的糊剂进行辐照以引发反应来获得产物。

  DOI：

  10.1081/scc-100106041

文献信息

• Efficient N-heterocyclic carbene nickel pincer complexes catalyzed cross coupling of benzylic ammonium salts with boronic acids
  作者：Xi-Yu Liu、Hai-Bo Zhu、Ya-Jing Shen、Jian Jiang、Tao Tu

  DOI：10.1016/j.cclet.2016.09.006

  日期：2017.2

  Abstract Pyridine-bridged bis-benzimidazolylidene nickel complexes exhibited very high catalytic activity toward cross coupling of inactive (hetero)aryl benzylic ammonium salts with (hetero)aryl and alkenyl boronic acids under mild reaction conditions. Even at 2 mol% catalyst loading, a wide range of substrates for both coupling partners with different steric and electronic properties were well tolerated

  摘要吡啶桥联的双苯并咪唑基亚乙基镍络合物在温和的反应条件下，对非活性（杂）芳基苄基铵盐与（杂）芳基和烯基硼酸的交叉偶联反应具有很高的催化活性。即使在催化剂负载量为2 mol％的情况下，两种具有不同空间和电子特性的偶合配偶体都可以很好地耐受各种底物。
• Scandium(<scp>III</scp>) trifluoromethanesulfonate-catalysed reductive Friedel–Crafts benzylation of aromatic compounds using arenecarbaldehydes and propane-1,3-diol
  作者：Teruhisa Tsuchimoto、Tamejiro Hiyama、Shin-ichi Fukuzawa

  DOI：10.1039/cc9960002345

  日期：——

  Scandium(III) trifluoromethanesulfonate catalyses the Friedel-Crafts benzylation of aromatic compounds with arenecarbaldehydes and propane-1,3-diol to produce, through a clean redox process, diarylmethanes in high to excellent yields.
• Superacid-Catalyzed Reductive Friedel−Crafts Reaction of Arenes Using Arenecarbaldehyde Acetals
  作者：Shin-ichi Fukuzawa、Teruhisa Tsuchimoto、Tamejiro Hiyama

  DOI：10.1021/jo961897e

  日期：1997.1.1

  Reaction of 2-aryl-1,3-dioxane with arenes in the presence of a catalytic amount of trifluoromethanesulfonic acid gave the corresponding diarylmethanes in good to excellent yields. The acid-catalyzed Friedel-Crafts benzylation of arenes could altenatively be carried out using arenecarbaldehyde and 1,3-propanediol. The reaction was assumed to proceed through a redox process involving hydride shift from the cyclic acetal moiety to the benzylic carbon. The hydride shift was confirmed by the reaction with 5-ethyl-2-phenyl-4,4,6,6-tetradeuterio-1,3-dioxane, wherein more than 90% deuterium was incorporated into the benzylic carbon of the diphenylmethane. Diphenylmethyl ether Ph(2)CHOCH(2)CH(2)CH(2)OH also reacted with benzene to afford diphenylmethane under the same reaction conditions, suggesting that the ether should be the plausible intermediate that underwent the hydride shift.
• Scandium(III) Triflate-Catalyzed Friedel−Crafts Alkylation Reactions
  作者：Teruhisa Tsuchimoto、Kazuo Tobita、Tamejiro Hiyama、Shin-ichi Fukuzawa

  DOI：10.1021/jo970599u

  日期：1997.10.1

  The Sc(OTf)(3)-catalyzed Friedel-Crafts alkylation reaction with an alcohol, an arenecarbaldehyde or an arenecarbaldehyde acetal as the alkylating agent affords a diarylmethane or an allylbenzene derivative highly selectively. The salient feature of this reaction is that only a catalytic amount of Sc(OTf)(3) can effect the reaction. Furthermore, Sc(OTf)(3) is recoverable and reusable after the synthetic reaction. The Sc(OTf)(3)-catalyzed benzylation using an arenecarbaldehyde and 1,3-propanediol or their acetal affords diarylmethane as a sole product in excellent yields in sharp contrast to the original Friedel-Crafts reaction. Since no reaction occurs in the absence of 1,3-propanediol, the reaction is considered to proceed through a redox process including a hydride shift. The hydride shift mechanism is strongly supported by the experimental evidence. The reaction of benzaldehyde with benzene in the presence of 1,3-propanediol-1,1,3,3,-d(4) gives rise to the deuterium incorporation into the benzylic carbon of diphenylmethane. Worthy of note is that 1,3-propanediol acts as the hydride source. Herein, diphenylmethyl 3-hydroxypropyl ether is assumed to be the most likely intermediate. In this reaction, Sc(OTf)(3) catalyst effectively promotes initial acetal formation, electrophilic aromatic substitution, and successive intramolecular hydride transfer.