1-(naphthalen-1-yl)-4-phenylbutan-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(naphthalen-1-yl)-4-phenylbutan-1-one
• 英文别名: 1-Naphthalen-1-yl-4-phenylbutan-1-one
• 化学式: C₂₀H₁₈O
• 分子量: 274.362
• InChiKey: RNTGDGYGWSIDRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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-(naphthalen-1-yl)-4-phenylbutan-1-one 在 氧气 、 copper diacetate 、 palladium diacetate 、 三氟乙酸 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以52%的产率得到(E)-1-(naphthalen-1-yl)-4-phenylbut-2-ene-1,4-dione
  参考文献：
  名称：

  酮的好氧氧化脱氢成1,4-烯酮

  摘要：

  通过钯催化的氧化脱氢，已经开发出一种有效且空前的从饱和酮合成1,4-二烯酮的策略。该协议采用分子氧作为唯一的氧化剂，代表了原子经济和逐步经济的过程。该方法显示出广泛的底物范围，良好的官能团耐受性和完全的E-立体选择性。通过氘标记实验和中间实验研究了反应机理。

  DOI：

  10.1021/acs.orglett.0c04174
• 作为产物：
  描述：

  1-碘萘 、 4-苯基丁腈 在 氯化镍二甲氧基乙烷 、 1,3-双(二苯基膦)丙烷 、 水 、 锌 作用下， 以 乙二醇二甲醚 为溶剂， 反应 36.0h， 以65%的产率得到1-(naphthalen-1-yl)-4-phenylbutan-1-one
  参考文献：
  名称：

  Nickel-Catalyzed Intermolecular Insertion of Aryl Iodides to Nitriles: A Novel Method to Synthesize Arylketones

  摘要：

  A novel procedure for the NiCl2(DME)/dppp/Zn system catalyzed intermolecular insertion of aryl iodides to nitriles was developed, which afforded variously substituted arylketone derivatives in moderate to good yields with tolerance of a wide variety of functional groups.

  DOI：

  10.1021/ol300153f

文献信息

• Intermolecular Addition Reaction to Alkenes of Acylmolybdenum Complexes Generated by Oxidative Addition of Aryl or Alkenyl Halides with Molybdenum(0) Carbonyl Complexes
  作者：Nobuharu Iwasawa、Kenichiro Sangu、Toru Watanabe、Jun Takaya

  DOI：10.1055/s-2007-973858

  日期：2007.4

  Acylmolybdenum species, generated by oxidative addition of aryl or alkenyl halides with molybdenum(0) carbonyl complex followed by carbon monoxide insertion, added to various kinds of alkenes intermolecularly to give simple addition products in good yields without formation of carbonylative Heck-type products.

  酰基钼物种，通过芳基或烯基卤化物与钼 (0) 羰基络合物的氧化加成，然后插入一氧化碳，分子间添加到各种烯烃中，以良好的收率得到简单的加成产物，而不会形成羰基化的 Heck 型产物。
• Palladium-catalyzed Dehydrogenative [3+3] Aromatization of Propyl Ketones and Allyl Carbonates
  作者：Kenta Koike、Satoshi Ueno

  DOI：10.1246/cl.220032

  日期：2022.4.5

  A Pd-catalyzed dehydrogenative [3+3] aromatization of 3-phenylpropyl ketones and allyl carbonates has been developed. The reaction gives various di- or tri-substituted aromatic ketones. The reaction consisting of five steps efficiently proceeded in a one-batch, one-manipulation setup. The postulated active species, η3-allyl palladium complex, works as a catalyst for triple dehydrogenations and mono

  已经开发了 3-苯丙基酮和碳酸烯丙酯的 Pd 催化脱氢 [3+3] 芳构化反应。该反应产生各种二或三取代的芳族酮。由五个步骤组成的反应在一批、一次操作的设置中有效地进行。假定的活性物质η 3 -烯丙基钯络合物可作为三重脱氢和单烯丙基化的催化剂，具有高底物控制。
• Metal‐Organic Framework Supported Copper Photoredox Catalysts for Iminyl Radical‐Mediated Reactions
  作者：Ben Ma、Qi Xia、Deyang Wang、Ji‐Kang Jin、Zekun Li、Qiu‐Jiang Liang、Meng‐Ying Sun、Dongyi Liu、Li‐Juan Liu、Hui‐Xing Shu、Jun Yang、Dan Li、Jian He

  DOI：10.1002/anie.202300233

  日期：——

  A binap-ligated copper dimer has been heterogenized on a pillar-layered MOF surface for the first time using a hydroxamic acid linker. This MOF-supported dimeric copper photocatalyst demonstrates much higher activity and recyclability than its homogeneous counterparts in intra- and intermolecular radical reactions of N-acyloxy imidates and O-acyl oximes.

  binap 连接的铜二聚体首次使用异羟肟酸接头在柱状层状 MOF 表面异质化。这种 MOF 负载的二聚铜光催化剂在N-酰氧基亚胺酸酯和O-酰基肟的分子内和分子间自由基反应中表现出比其均相对应物更高的活性和可回收性。
• Nickel-Catalyzed Intermolecular Insertion of Aryl Iodides to Nitriles: A Novel Method to Synthesize Arylketones
  作者：Jen-Chieh Hsieh、Yen-Chung Chen、An-Yi Cheng、Hsiao-Chun Tseng

  DOI：10.1021/ol300153f

  日期：2012.3.2

  A novel procedure for the NiCl2(DME)/dppp/Zn system catalyzed intermolecular insertion of aryl iodides to nitriles was developed, which afforded variously substituted arylketone derivatives in moderate to good yields with tolerance of a wide variety of functional groups.
• Aerobic Oxidative Dehydrogenation of Ketones to 1,4-Enediones
  作者：Bao-Yin Zhao、Xing-Long Zhang、Rui-Li Guo、Meng-Yue Wang、Ya-Ru Gao、Yong-Qiang Wang

  DOI：10.1021/acs.orglett.0c04174

  日期：2021.2.19

  An efficient and unprecedented strategy for the synthesis of 1,4-enediones from saturated ketones has been developed via palladium-catalyzed oxidative dehydrogenation. The protocol employs molecular oxygen as the sole oxidant and represents an atom- and step-economic process. The approach showed broad substrate scope, good functional group tolerance, and complete E-stereoselectivity. The reaction mechanism

  通过钯催化的氧化脱氢，已经开发出一种有效且空前的从饱和酮合成1,4-二烯酮的策略。该协议采用分子氧作为唯一的氧化剂，代表了原子经济和逐步经济的过程。该方法显示出广泛的底物范围，良好的官能团耐受性和完全的E-立体选择性。通过氘标记实验和中间实验研究了反应机理。