(2-(methoxymethyl)phenyl)(phenyl)methanone | 108683-16-5

• 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: (2-(methoxymethyl)phenyl)(phenyl)methanone
• 英文别名: [2-(Methoxymethyl)phenyl]-phenylmethanone
• CAS: 108683-16-5
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: KMHGTFAMBCKNRW-UHFFFAOYSA-N

物化性质

• 沸点：
  366.0±25.0 °C(Predicted)
• 密度：
  1.094±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-(methoxymethyl)phenyl)(phenyl)methanone 在 吡啶 、 氯化亚砜 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (3aR,4S)-4-Methoxy-9-phenyl-3a,4-dihydro-3H-naphtho[2,3-c]furan-1-one
  参考文献：
  名称：

  A Convenient Method for the Synthesis of9-Aryl-4-methoxynaphtho[2,3-c]furan-1(3H)-ones

  摘要：

  A three-step procedure for the synthesis of the title lignan lactone derivatives is described. The route involves a tandem Michael addition/cyclization reaction between o-aroyl-alpha-methoxybenzyllithiums, which are generated in situ by the treatment of aryl 2-methoxymethylphenyl ketones with lithium diisopropylamide (LDA) in THF at -78 degrees C, and furan-2(5H)-one to give the corresponding 9-aryl-9-hydroxy-4-methoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1 (3H)-ones in moderate to good yields. These products are readily transformed into the title naphthofuranones by dehydration with thionyl. chloride in pyridine, followed by aromatization with palladium on activated carbon.

  DOI：

  10.3987/com-97-7864
• 作为产物：
  描述：

  2-methoxymethyl-α-phenylbenzyl alcohol 在 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以77%的产率得到(2-(methoxymethyl)phenyl)(phenyl)methanone
  参考文献：
  名称：

  A Convenient Method for the Synthesis of9-Aryl-4-methoxynaphtho[2,3-c]furan-1(3H)-ones

  摘要：

  A three-step procedure for the synthesis of the title lignan lactone derivatives is described. The route involves a tandem Michael addition/cyclization reaction between o-aroyl-alpha-methoxybenzyllithiums, which are generated in situ by the treatment of aryl 2-methoxymethylphenyl ketones with lithium diisopropylamide (LDA) in THF at -78 degrees C, and furan-2(5H)-one to give the corresponding 9-aryl-9-hydroxy-4-methoxy-3a,4,9,9a-tetrahydronaphtho[2,3-c]furan-1 (3H)-ones in moderate to good yields. These products are readily transformed into the title naphthofuranones by dehydration with thionyl. chloride in pyridine, followed by aromatization with palladium on activated carbon.

  DOI：

  10.3987/com-97-7864

文献信息

• Construction of Benzocyclobutenes Enabled by Visible‐Light‐Induced Triplet Biradical Atom Transfer of Olefins
  作者：Jiaxin Liu、Tonggang Hao、Ling Qian、Min Shi、Yin Wei

  DOI：10.1002/anie.202204515

  日期：2022.9.5

  Benzocyclobutanol and benzocyclobutylamine derivatives have been obtained by visible-light-induced triplet biradical atom transfer of olefins. The reaction mechanism was investigated by deuterium-labeling and kinetic quenching experiments, as well as DFT calculations.

  苯并环丁醇和苯并环丁胺衍生物是通过可见光诱导的烯烃三重态双自由基原子转移获得的。通过氘标记和动力学猝灭实验以及DFT计算研究了反应机理。
• Direct insertion into the C–C bond of unactivated ketones with NaH-mediated aryne chemistry
  作者：Fan Luo、Chen-Long Li、Peng Ji、Yuxin Zhou、Jingjing Gui、Lingyun Chen、Yuejia Yin、Xinyu Zhang、Yanwei Hu、Xiaobei Chen、Xuejun Liu、Xiaodong Chen、Zhi-Xiang Yu、Wei Wang、Shi-Lei Zhang

  DOI：10.1016/j.chempr.2023.05.032

  日期：2023.9

  Density functional theory (DFT) calculations reveal that the two adjacent iodines in o-diiodoarenes play critical roles in the formation of aryne. The nucleophilic attack of hydride to the electrophilic iodine requires that the adjacent iodine act as a directing group to accelerate this process, whereas mono-substituted iodobenzene lacking the neighboring-group participation makes it difficult. The in-situ-formed

  在这里，我们记录了以“旧”邻二碘芳烃作为芳炔祖体的芳炔化学的重新发明。我们建立了 NaH 介导的活化策略，以受控方式生成高反应性芳炔物种。所得芳炔可以有效地参与与未活化酮的C-C σ键插入反应，这是现有方法难以实现的。密度泛函理论 (DFT) 计算表明o中的两个相邻碘-二碘芳烃在芳炔的形成中起关键作用。氢化物对亲电子碘的亲核攻击需要邻近的碘充当导向基团来加速这一过程，而缺乏邻近基团参与的单取代碘苯则使其变得困难。酮原位形成的烯醇化物被建议采用四聚体聚集体与芳烃反应，这解释了具有大取代基的底物的高区域化学性。
• 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.
• METHOD FOR TACK FREE SURFACE PHOTOCURING OF FREE RADICALLY POLYMERIZABLE RESINS UNDER VISIBLE LIGHT PHOTOEXCITATION
  申请人：BASF SE

  公开号：EP2303932A1

  公开（公告）日：2011-04-06
• US4435496A
  申请人：——

  公开号：US4435496A

  公开（公告）日：1984-03-06