1-butyl-4-phenylnaphthalene

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-butyl-4-phenylnaphthalene
• 化学式: C₂₀H₂₀
• 分子量: 260.379
• InChiKey: LOXBRDAJUAJVIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1-Butyl-4-phenylnaphthalene-1,4-diol 在 氢碘酸 作用下， 以 四氢呋喃 为溶剂， 生成 1-butyl-4-phenylnaphthalene
  参考文献：
  名称：

  竞争性二烯酮-苯酚类型重排用于2,4-二取代-萘-1-醇的区域选择性制备

  摘要：

  描述了通过二烯酮-苯酚重排的变体的2,4-取代的萘-1-醇的区域选择性制备。

  DOI：

  10.1016/s0040-4039(00)80619-x

文献信息

• Experimental and Computational Studies towards Chemoselective C−F over C−Cl Functionalisation: Reversible Oxidative Addition is the Key
  作者：Emily Jacobs、Sinead T. Keaveney

  DOI：10.1002/cctc.202001462

  日期：2021.1.20

  Catalytic cross‐coupling is a valuable tool for forming new carbon‐carbon and carbon‐heteroatom bonds, allowing access to a variety of structurally diverse compounds. However, for this methodology to reach its full potential, precise control over all competing cross‐coupling sites in poly‐functionalised building blocks is required. Carbon‐fluorine bonds are one of the most stable bonds in organic chemistry

  催化交叉偶联是形成新的碳-碳和碳-杂原子键的宝贵工具，可用于获得各种结构多样的化合物。但是，要使这种方法发挥其全部潜力，就需要对多功能构建块中所有竞争的交叉耦合位点进行精确控制。碳氟键是有机化学中最稳定的键之一，在C-F上的氧化加成比在其他C-卤化物键上的加成困难得多。因此，如果要在氧化加成步骤中诱导选择性，化学选择性官能化C-F在多卤代芳烃中的位置的方法的开发将非常具有挑战性。但是，金属卤化物络合物与母体卤代芳烃的反应性呈现出不同的趋势，与金属氟化物的复合物对金属转移反应非常活跃。在当前的工作中，我们试图利用Ni-Cl和Ni-F中间体的发散反应性来开发化学选择性CF官能化方案，其中选择性由过渡金属化步骤控制。我们的实验研究表明，这种方法是可行的，许多镍催化剂显示出在无碱条件下促进1-氟萘的Hiyama交叉偶联，而没有与1-氯萘的交叉偶联。计算和实验研究表明，可逆的C-Cl氧化加成对于选择
• Triflic acid catalysed regioselective synthesis of substituted naphthalenes by benzannulation of carbonyls with alkynes
  作者：Vanajakshi Gudla、Mokhamatam Sudheer、Chinthu Joginarayana Rao、Paul Douglas Sanasi、Venkateswara Rao Battula

  DOI：10.1016/j.tet.2021.132214

  日期：2021.6

  An interesting and facile triflic acid catalysed annulation of α-aryl carbonyls with arylalkynes is presented for the regioselective synthesis of substituted naphthalenes. The annulation reaction involves a sequence of electrophilic attack of carbonyl on arylalkyne and benzannulation catalysed by triflic acid. The present catalyst effects this transformation at room temperature itself. Intramolecular

  提出了一种有趣且容易的三氟甲磺酸催化的α-芳基羰基与芳基炔的环化反应，用于取代萘的区域选择性合成。环化反应涉及羰基对芳基炔烃的亲电进攻和由三氟甲磺酸催化的苯环化的序列。本发明的催化剂在室温下自身实现这种转变。本布朗斯台德酸催化的分子内形式以优异的产率提供了包含与环系统稠合的1-芳基萘核的化合物。
• 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。
• Gold-Catalyzed Electrophilic Addition to Arylalkynes. A Facile Method for the Regioselective Synthesis of Substituted Naphthalenes
  作者：Rengarajan Balamurugan、Vanajakshi Gudla

  DOI：10.1021/ol900863d

  日期：2009.7.16

  An interesting gold-catalyzed electrophilic addition to arylalkyne to synthesize substituted naphthalenes has been presented. Different metal hexafluoroantimonates have also been found to effect the transformation. Counter anion and oxo- and alkynophilicities of catalytic gold species might play an important role in this annulation reaction.

  已经提出了一种有趣的金催化的亲电加成到芳基炔烃上以合成取代的萘。还发现了不同的六氟锑酸金属实现转化。催化金物种的抗衡阴离子以及氧合和亲核性可能在该环化反应中起重要作用。
• Electrochemically Enabled Carbohydroxylation of Alkenes with H₂O and Organotrifluoroborates
  作者：Peng Xiong、Hao Long、Jinshuai Song、Yaohui Wang、Jian-Feng Li、Hai-Chao Xu

  DOI：10.1021/jacs.8b08592

  日期：2018.12.5

  Unprecedented hydroxy-alkynylation and -alkenylation reactions of arylalkenes have been developed through electrochemically enabled addition of an organotrifluoroborate reagent and H2O across the double bond of the alkene. The use of electrochemistry to promote these oxidative alkene 1,2-difunctionalization reactions not only obviates the need for transition-metal catalysts and oxidizing reagents but also ensures high regio- and chemoselectivity to afford homopropargylic or homoallylic alcohols. The possibility of extending the electro-chemical alkene difunctionalization strategy to other alkene carbo-heterofunctionalization reactions has been demonstrated.