1,2-bis(1-methoxycarbonyl-2-naphthyl)ethane

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-bis(1-methoxycarbonyl-2-naphthyl)ethane
• 英文别名: 1,2-bis[1-(methoxycarbonyl)naphthalen-2-yl]ethane；methyl 2-[2-(1-methoxycarbonylnaphthalen-2-yl)ethyl]naphthalene-1-carboxylate
• 化学式: C₂₆H₂₂O₄
• 分子量: 398.458
• InChiKey: JEGYXNJBTOELHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基萘 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 溴 、 碘 、 铁粉 、 potassium carbonate 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 四氯化碳 、 正己烷 、 丁酮 、 苯 为溶剂， 反应 5.03h， 生成 3-[(1-(methoxycarbonyl)naphthalen-2-yl)methyl]-2,4,6-trimethylphenol 、 6-{[1-(methoxycarbonyl)naphthalen-2-yl]methyl}-2,4,6-trimethylcyclohexa-2,4-dien-1-one 、 1,2-bis(1-methoxycarbonyl-2-naphthyl)ethane
  参考文献：
  名称：

  Improved efficiency and product selectivity in the photo-Claisen-type rearrangement of an aryl naphthylmethyl ether using a microreactor/flow system

  摘要：

  紫外线（UV）辐射2-[(2,4,6-三甲基苯氧基)甲基]-1-(甲氧基羰基)萘可促进光化学反应，生成来自光-克莱森型邻位重排的环己-2,4-二烯酮产物、来自间位重排的酚衍生物，以及1-甲氧基羰基-2-甲基萘和1,2-双[1-(甲氧基羰基)萘-2-基]乙烷。当该过程在微反应器/流动系统中进行时，其效率显著提高，产物选择性得到改善。微反应器/流动系统对效率和产物选择性的影响归因于更有效的光吸收和次级反应的抑制。

  DOI：

  10.1007/s11164-012-0650-6

文献信息

• A novel photorearrangement of aryl naphthylmethyl ethers. Formation of cyclohexa-2,4-dienone derivatives
  作者：Yasuharu Yoshimi、Akira Sugimoto、Hajime Maeda、Kazuhiko Mizuno

  DOI：10.1016/s0040-4039(98)00877-6

  日期：1998.6

  Irradiation of a benzene solution containing 1-methoxycarbonyl-2-naphthylmethyl 2,6-dimethyl substituted phenyl ethers (1a,b) afforded cyclohexa-2,4-dienone derivatives (2a,b) as initial rearranged products via CO bond cleavage and meta substituted phenols (3a,b) which were formed by subsequent photorearrangement of 2a,b.

  辐照含1-甲氧羰基-2-萘甲基2,6-二甲基取代的苯基醚的苯溶液（1a，b），通过C bondO键断裂，得到环己-2,4-二烯酮衍生物（2a，b），作为初始重排产物以及间位取代的苯酚（3a，b），其通过随后的2a，b的光重排而形成。
• Intramolecular 9-membered hydrogen bonding of 2-arylmethylphenols having carbonyl groups at 2′-position
  作者：Yasuharu Yoshimi、Hajime Maeda、Minoru Hatanaka、Kazuhiko Mizuno

  DOI：10.1016/j.tet.2004.08.007

  日期：2004.10

  Thermodynamic parameters of nine-membered intramolecular hydrogen bonding between carbonyl groups and phenolic hydroxyl groups of 2-arylmethylphenols having methoxycarbonyl, dimethylcarbamoyl, and formyl groups were determined by variable temperature 1H NMR studies and van't Hoff analysis. The enthalpy of the hydrogen bonding was related to the electron-withdrawing ability of the substituents on the

  通过可变温度1 H NMR研究和van't Hoff分析，确定了具有甲氧基羰基，二甲基氨基甲酰基和甲酰基的2-芳基甲基苯酚的羰基和酚羟基之间的九元分子内氢键的热力学参数。氢键的焓与苯酚上的取代基的吸电子能力和羰基的碱性有关。氢键的熵损失取决于酚基团的旋转自由度。
• Direct Observation of 2-(1-Methoxycarbonylnaphthyl)methyl Radical via Photo-Claisen Type Rearrangement
  作者：Yasuharu Yoshimi、Kazuhiko Mizuno、Hajime Maeda、Nobuyuki Ichinose、Tomoko Tanaka、Shun-ichi Kawanishi

  DOI：10.1246/cl.2001.252

  日期：2001.3

  The photo-Claisen type rearrangement of 2-(1-methoxycarbonylnaphthyl)methyl phenyl ether derivatives 1a–f was investigated. The 2-(1-methoxycarbonylnaphthyl)methyl radical and its fluorescence by use of two colored laser flash photolysis (LFP) technique were directly observed as a reactive intermediate. The reactivity of the photorearrangement depended on the p-substituents on the phenoxy group.

  研究了 2-(1-甲氧基羰基萘基)甲基苯基醚衍生物 1a-f 的光克莱森型重排。2-(1-甲氧基羰基萘基)甲基自由基及其荧光通过使用两种彩色激光闪光光解(LFP)技术被直接观察为反应中间体。光重排的反应性取决于苯氧基上的 p 取代基。
• Improved efficiency and product selectivity in the photo-Claisen-type rearrangement of an aryl naphthylmethyl ether using a microreactor/flow system
  作者：Hajime Maeda、Satoshi Nashihara、Hirofumi Mukae、Yasuharu Yoshimi、Kazuhiko Mizuno

  DOI：10.1007/s11164-012-0650-6

  日期：2013.1

  Ultraviolet (UV) irradiation of 2-[(2,4,6-trimethylphenoxy)methyl]-1-(methoxycarbonyl)naphthalene promotes a photochemical reaction that gives a cyclohexa-2,4-dienone product arising from a photo-Claisen-type ortho-rearrangement and a phenol derivative arising from a meta-rearrangement, along with 1-methoxycarbonyl-2-methylnaphthalene and 1,2-bis[1-(methoxycarbonyl)naphthalen-2-yl]ethane. When this process is carried out in a microreactor/flow system, its efficiency is dramatically enhanced and selectivity of products is improved. The effects on efficiency and product selectivity caused by the microreactor/flow system are attributed to more efficient light absorption and the suppression of secondary reactions.

  紫外线（UV）辐射2-[(2,4,6-三甲基苯氧基)甲基]-1-(甲氧基羰基)萘可促进光化学反应，生成来自光-克莱森型邻位重排的环己-2,4-二烯酮产物、来自间位重排的酚衍生物，以及1-甲氧基羰基-2-甲基萘和1,2-双[1-(甲氧基羰基)萘-2-基]乙烷。当该过程在微反应器/流动系统中进行时，其效率显著提高，产物选择性得到改善。微反应器/流动系统对效率和产物选择性的影响归因于更有效的光吸收和次级反应的抑制。