1-methyl-4-phenylnaphthalene | 13280-69-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-methyl-4-phenylnaphthalene
• 英文别名: 1-Methyl-4-phenyl-naphthalin；4-Methyl-1-phenyl-naphthalin；4-Phenyl-1-methyl-naphthalin
• CAS: 13280-69-8
• 化学式: C₁₇H₁₄
• 分子量: 218.298
• InChiKey: LDSUZJOZRKYGNI-UHFFFAOYSA-N

物化性质

• 沸点：
  349.2±17.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-methyl-4-phenylnaphthalene 、 N-溴代丁二酰亚胺(NBS) 生成 1-bromomethyl-4-phenylnaphthalene
  参考文献：
  名称：

  KALTENBRONN J. S., J. MED. CHEM., 1977, 20, NO 4, 596-598

  摘要：

  DOI：
• 作为产物：
  描述：

  5,5-二苯基-2-戊酮 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 1-methyl-4-phenylnaphthalene
  参考文献：
  名称：

  Quillet,J.-P.; Dreux,J., Bulletin de la Societe Chimique de France, 1966, p. 645 - 652

  摘要：

  DOI：

文献信息

• NHC-Nickel Catalyzed C–N Bond Cleavage of Mono-protected Anilines for C–C Cross-Coupling
  作者：Zheng-Bing Zhang、Ji-Bao Xia

  DOI：10.1021/acs.orglett.0c03660

  日期：2020.12.18

  A Ni-catalyzed aryl C–N bond cleavage of mono-protected anilines, N-arylsulfonamides, has been developed. A new N-heterocyclic carbene derived from benzoimidazole shows high reactivity for the C–N cleavage/C–C cross-coupling reaction. The ortho-directing group is not required to break the C–N bond of sulfonyl-protected anilines, which are not limited to π-extended anilines. The mechanistic studies

  已经开发了单保护的苯胺（N-芳基磺酰胺）的Ni催化的芳基C–N键裂解。一种新的衍生自苯并咪唑的N杂环卡宾对C–N裂解/ CC交叉偶联反应具有高反应活性。的邻位不要求导向基团打破磺酰基-保护的苯胺，这不限于π扩展苯胺的C-N键。机理研究表明，磺酰胺基镁盐是关键的偶联中间体。
• Ruthenium‐Catalyzed Cycloisomerization of 2‐Alkynylstyrenes via 1,2‐Carbon Migration That Leads to Substituted Naphthalenes
  作者：Takuma Watanabe、Haruka Abe、Yuichiro Mutoh、Shinichi Saito

  DOI：10.1002/chem.201802413

  日期：2018.8.9

  ruthenium‐catalyzed carbocyclization of 2‐alkynylstyrenes that involves a very rare 1,2‐carbon migration of internal alkynes is reported. Various 1,2‐di ‐and 1,4,7‐trisubstituted naphthalenes are synthesized. Mechanistic studies revealed that this reaction proceeds via a disubstituted vinylidene complex as the key intermediate by 1,2‐carbon migration of the 2‐alkynylstyrenes.

  据报道，钌催化的2-炔基苯乙烯的碳环化涉及极少的内部炔烃的1,2-碳迁移。合成了各种1,2-二和1,4,7-三取代的萘。机理研究表明，该反应通过二取代的亚乙烯基配合物进行，该配合物是2-炔基苯乙烯的1,2-碳迁移的关键中间体。
• Ring-Opening/Expansion Rearrangement of Cycloprop[2,3]inden-1-ols Catalyzed by<i>p-</i>Toluenesulfonic Acid
  作者：Pei-Fang Li、Cheng-Bo Yi、Shu-Jian Ren、Jin Qu

  DOI：10.1002/adsc.201600246

  日期：2016.6.30

  1‐hydroxymethylindenes (which could then be converted to benzofulvenes through a dehydration reaction) or naphthalenes by the rearrangement of cycloprop[2,3]inden‐1‐ols is reported. The effect of the cyclopropyl ring substitution pattern on ring‐opening/expansion rearrangements of the substrates was systemically studied.

  据报道，通过环丙[2,3]茚满-1-醇的重排，可以生成1-羟基甲基茚（然后可通过脱水反应转化为苯并富烯）或萘的不同方法。系统研究了环丙基环取代模式对底物的开环/扩展重排的影响。
• 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。