1-[2-(萘-2-基)苯基]乙酮 | 1183936-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-[2-(萘-2-基)苯基]乙酮
• 英文名称: 1-[2-(naphthalen-2-yl)phenyl]ethanone
• 英文别名: 1-(2-Naphthalen-2-ylphenyl)ethanone
• CAS: 1183936-56-2
• 化学式: C₁₈H₁₄O
• 分子量: 246.309
• InChiKey: SMJREIXGXBULGV-UHFFFAOYSA-N

物化性质

• 沸点：
  418.5±24.0 °C(Predicted)
• 密度：
  1.117±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-[2-(萘-2-基)苯基]乙酮 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 C₁₈H₁₅NO
  参考文献：
  名称：

  酰基肟的可见光促进亚甲基基自由基形成：吡啶，喹啉和菲啶的统一方法

  摘要：

  已经建立了涉及可见光诱导的亚胺基自由基形成的统一策略，用于从酰基肟中构建吡啶，喹啉和菲啶。用FAC - [的Ir（ppy）3 ]作为催化剂photoredox，酰基肟通过1e中转化-还原成亚氨基自由基中间体，然后行分子内均裂芳族取代（HAS），得到含有N-芳烃其中。这些反应在室温下以宽范围的底物以高收率进行。这种可见光诱导的亚胺基自由基形成策略已成功地应用于五步精简合成苯并[ c ]菲啶生物碱。

  DOI：

  10.1002/anie.201411342
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 生成 1-[2-(萘-2-基)苯基]乙酮
  参考文献：
  名称：

  钌（0）选择性碳氮裂解催化苯胺与有机硼烷的交叉偶联

  摘要：

  中性碳-氮键的选择性活化具有非常重要的合成重要性，因为胺是有机和生物活性分子中最普遍的基序之一。在本文中，我们报告了Ru（0）催化通过Ru 3（CO）12的组合实现的通用苯胺衍生物中性C（芳基）–N键的中性C（芳基）–N键的选择性裂解和亚胺辅助剂。这些温和条件为原位水解提供了一条通往高价值联芳酮和联芳醛的直接途径。广泛的有机硼烷和苯胺可以与高的C–N裂解选择性结合在一起。最关键的是，在通常具有动力学上更有利的C（芳基）-H键存在的情况下，该反应可实现精妙的C（芳基）-N键活化选择性。该方法通过利用Ru（0）催化剂体系的正交性质和苯胺的无痕亲核性质，为官能化三联苯的构建提供了策略。

  DOI：

  10.1021/acscatal.9b02440

文献信息

• <i>N</i>-Bromosuccinimide-Induced C–H Bond Functionalization: An Intramolecular Cycloaromatization of Electron Withdrawing Group Substituted 1-Biphenyl-2-ylethanone for the Synthesis of 10-Phenanthrenol
  作者：Ya-Ting Jiang、Zhen-Zhen Yu、Ya-Kai Zhang、Bin Wang

  DOI：10.1021/acs.orglett.8b01160

  日期：2018.7.6

  intramolecular cycloaromatization for the synthesis of 10-phenanthrenols from electron-withdrawing group substituted 1-biphenyl-2-ylethanones is described. The in situ generated bromide was designed to act as an initiator for the radical C–H bond activation. An oxidative cross-dehydrogenative coupling reaction of a highly active C–H bond with an inert C–H bond readily occurs under mild conditions without

  描述了NBS诱导的分子内环芳环化，该环化是从吸电子基团取代的1-联苯-2-丙酮酮合成10-菲咯啉。原位生成的溴化物被设计成可作为自由基C–H键活化的引发剂。高活性CH键与惰性CH键的氧化交叉脱氢偶联反应在温和条件下很容易发生，不需要过渡金属或强氧化剂。
• Selective Monoarylation of Aromatic Ketones via C–H Bond Cleavage by Trialkylphosphine Ruthenium Catalysts
  作者：Issei Suzuki、Hikaru Kondo、Takuya Kochi、Fumitoshi Kakiuchi

  DOI：10.1021/acs.joc.9b01756

  日期：2019.10.18

  RuHCl(CO)(PiPr3)2, CsF, and a styrene derivative was found to be applicable to selective monoarylation of aromatic ketones via ortho C-H bond cleavage. The reaction of 2'-methoxyacetophenone with arylboronates gave C-H arylation products without cleaving the ortho C-O bond. Acetophenone was also converted to monoarylation products with high selectivity. Cyclohexanone was found to be an effective solvent

  发现由RuHCl（CO）（PiPr3）2，CsF和苯乙烯衍生物组成的催化剂体系可用于通过邻位CH键裂解选择性芳族酮单芳基化。2'-甲氧基苯乙酮与芳基硼酸酯的反应得到CH芳基化产物，而没有裂解邻位CO键。苯乙酮也以高选择性转化为单芳基化产物。发现使用催化剂体系，环己酮是CH芳基化的有效溶剂。
• Formation of a carbonyl group ortho to a biaryl structure or a 6H-dibenzopyran by a palladium/norbornene-catalyzed ordered reaction sequence
  作者：Nicola Della Ca'、Marco Fontana、Di Xu、Mirko Cremaschi、Riccardo Lucentini、Zhi-Ming Zhou、Marta Catellani、Elena Motti

  DOI：10.1016/j.tet.2015.05.110

  日期：2015.9

  Developments are reported in the catalytic synthesis of biaryls containing an ortho-carbaldehyde or 6H-dibenzopyrans in the presence of palladium/norbornene as catalyst. The reaction of o-substituted aryl iodides and o-bromobenzyl alcohols proceeds by unsymmetrical aryl-aryl coupling to form a seven-membered oxapalladacycle intermediate, which may undergo an intramolecular redox process to form carbonyl groups or a C-O coupling to six-membered cyclic ethers. The predominant formation of di-benzopyrans as well as of biaryl structures containing the oxidized CHO group in one ring and the reduced CH2OH in the other is described along with some mechanistic insights. (C) 2015 Elsevier Ltd. All rights reserved.
• Cobalt-Catalyzed <i>Ortho</i>-Arylation of Aromatic Imines with Aryl Chlorides
  作者：Ke Gao、Pin-Sheng Lee、Chong Long、Naohiko Yoshikai

  DOI：10.1021/ol301934y

  日期：2012.8.17

  An ortho-arylation reaction of aromatic imines with aryl chlorides has been achieved using a cobalt N-heterocyclic carbene catalyst in combination with a neopentyl Grignard reagent. The reaction takes place at room temperature to afford biaryl products in moderate to good yields.
• A Sequential Pd/Norbornene-Catalyzed Process Generates <i>o-</i>Biaryl Carbaldehydes or Ketones via a Redox Reaction or 6<i>H</i>-Dibenzopyrans by C–O Ring Closure
  作者：Elena Motti、Nicola Della Ca’、Di Xu、Anna Piersimoni、Elena Bedogni、Zhi-Ming Zhou、Marta Catellani

  DOI：10.1021/ol302889t

  日期：2012.11.16

  o-Biaryl carbaldeydes and ketones are obtained through the one-pot reaction of o-aryl iodides with o-bromobenzyl alcohols under the catalytic action of Pd and norbornene, in the presence of a base. The same reaction can also give dibenzopyrans by Pd and norbornene catalysis with a different termination, leading to C-O ring closure. In both cases the process first leads to a five-membered palladacycle, which controls C-C coupling, then to a seven-membered oxapalladacycle, which gives aldehydes and ketones or dibenzopyrans.