4-methyl-1,2-diphenylnaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methyl-1,2-diphenylnaphthalene
• 化学式: C₂₃H₁₈
• 分子量: 294.396
• InChiKey: FEZQUOKASQAAJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  2-(苄基)苯甲醛 在 manganese(IV) oxide 、 正丁基锂 、 2-二环己基膦-2′,4′,6′-三异丙基联苯金(I) 双(三氟甲烷磺酰)亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.67h， 生成 4-methyl-1,2-diphenylnaphthalene
  参考文献：
  名称：

  金（I）催化的苄基C（sp 3）H键的功能化。

  摘要：

  AbstractThe selective activation/functionalization of benzhydryl C(sp3)H bonds is documented. The gold complex XPhosAuNTf2 turned out to be an efficient catalyst (5 mol%) to transform readily available propargylic esters into di‐ or trisubstituted naphthalenes in high yield. A 1,5‐hydride shift is postulated as the key step of the cascade reaction sequence.magnified image

  DOI：

  10.1002/adsc.201300525

文献信息

• Synthesis of Substituted Naphthalenes by 1,4-Palladium Migration Involved Annulation with Internal Alkynes
  作者：Dong Wei、Tian-Jiao Hu、Chen-Guo Feng、Guo-Qiang Lin

  DOI：10.1002/cjoc.201800169

  日期：2018.8

  The palladium catalyzed annulation of 1‐bromo‐2‐vinylbenzene derivatives with internal alkynes was realized for the efficient synthesis of substituted naphthalenes. A controllable aryl to vinylic 1,4‐palladium migration process is the key for success.

  为了有效合成取代的萘，实现了钯催化的1-溴-2-乙烯基苯衍生物与内部炔的环化反应。可控的芳基向乙烯基1,4-钯迁移过程是成功的关键。
• MeOTf-catalyzed formal [4 + 2] annulations of styrene oxides with alkynes leading to polysubstituted naphthalenes through sequential electrophilic cyclization/ring expansion
  作者：Song Zou、Zeyu Zhang、Chao Chen、Chanjuan Xi

  DOI：10.1016/j.cclet.2021.12.012

  日期：2022.6

  MeOTf-catalyzed formal [4 + 2] annulation of styrene oxides with alkynes to afford polysubstituted naphthalenes has been realized, which undergoes sequential electrophilic cyclization/ring expansion. A range of substrates were tolerated in the formation of naphthalene derivatives with high regioselectivity in satisfactory yields. The reaction could also be carried out on gram scale.

  已经实现了 MeOTf 催化的氧化苯乙烯与炔烃的形式 [4 + 2] 环化以提供多取代的萘​​，其经历顺序的亲电环化/扩环。一系列底物在萘衍生物的形成过程中具有高区域选择性和令人满意的收率。该反应也可以以克级进行。
• HNTf₂-Catalyzed Regioselective Preparation of Polysubstituted Naphthalene Derivatives Through Alkyne–Aldehyde Coupling
  作者：Sudipta Ponra、Maxime R. Vitale、Véronique Michelet、Virginie Ratovelomanana-Vidal

  DOI：10.1021/acs.joc.5b00353

  日期：2015.3.20

  We report herein the preparation of polysubstituted naphthalene derivatives by the original Brønsted-acid-catalyzed benzannulation reaction of phenylacetaldehydes with alkynes. This reaction, which was usually performed with Lewis acids under thermal activation, is efficiently promoted by 15 mol % of triflimide (HNTf2) at room temperature under metal-free and mild reaction conditions and leads with

  我们在这里报道了通过苯乙醛与炔烃的原始布朗斯台德酸催化苯环化反应制备多取代的萘​​衍生物。通常在无金属和温和的反应条件下，室温下用15摩尔％的三氟甲酰亚胺（HNTf 2）可以有效地促进该反应，该反应通常用路易斯酸在热活化下进行。官能化萘的收率为41–78％。提出了催化循环以及该催化体系在环氧化物和乙缩醛衍生物的相关苯环化转化中的一些进一步应用。
• A New Titanium Tetrachloride Mediated Annulation of α-Aryl-Substituted Carbonyl Compounds with Alkynes:  A Simple and Highly Efficient Method for the Regioselective Synthesis of Polysubstituted Naphthalene Derivatives
  作者：George W. Kabalka、Yuhong Ju、Zhongzhi Wu

  DOI：10.1021/jo034330o

  日期：2003.10.1

  A new straightforward procedure has been developed for the synthesis of polysubstituted naphthalene derivatives. The reaction of alpha-aryl-substituted carbonyl compounds with terminal or internal alkynes in the presence of TiCl4 regioselectively generates substituted naphthalene derivatives in good to excellent yields.

  已经开发了用于合成多取代的萘​​衍生物的新的直接方法。在TiCl4的存在下，α-芳基取代的羰基化合物与末端或内部炔烃的反应可以区域选择性地生成取代的萘衍生物，收率好至极好。
• Copper-catalyzed electrosynthesis of 1-acyl-2,2-diphenylcyclopropanes and their behaviour in acidic medium
  作者：Sylvain Oudeyer、Eric Léonel、Jean Paul Paugam、Jean-Yves Nédélec

  DOI：10.1016/s0040-4020(02)01620-4

  日期：2003.2

  The formation of 1-acyl-2,2-diphenylcyclopropanes is performed under mild electrochemical conditions. These cyclopropane derivatives, through acid-catalyzed ring-opening, lead to γ,γ-diphenyl-β,γ-unsaturated carbonyl compounds which evolve into either substituted naphthalenes, or β-benzhydryl-α,β-cycloalkenones depending on the acyclic or cyclic nature of the intermediate allyl ketone.

  1-酰基-2，2-二苯基环丙烷的形成在温和的电化学条件下进行。这些环丙烷衍生物通过酸催化的开环反应，生成γ，γ-二苯基-β，γ-不饱和羰基化合物，根据无环或环状，这些化合物演变为取代的萘或β-苯甲酰基-α，β-环烯酮。中间烯丙基酮的性质。