1,6-methano[10]annulene-3,4-dicarboxylic anhydride | 1233975-60-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,6-methano[10]annulene-3,4-dicarboxylic anhydride
• 英文别名: 5-Oxatricyclo[7.4.1.03,7]tetradeca-1(13),2,7,9,11-pentaene-4,6-dione；5-oxatricyclo[7.4.1.03,7]tetradeca-1(13),2,7,9,11-pentaene-4,6-dione
• CAS: 1233975-60-4
• 化学式: C₁₃H₈O₃
• 分子量: 212.205
• InChiKey: WDACAVXAKCRSJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,6-methano[10]annulene-3,4-dicarboxylic anhydride 在 盐酸羟胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 5.0h， 以78%的产率得到N-hydroxy-1,6-methano[10]annulene-3,4-dicarboximide
  参考文献：
  名称：

  N-羟基-1,6-甲基[10]环戊烯-3,4-二二甲酰亚胺/ Co（OAc）2：烷基芳烃好氧氧化的新型催化体系

  摘要：

  烷基苯在温和的条件下，通过使用N-羟基-1,6-甲基[10]环戊烯-3,4-二羧酸二亚胺（2）和乙酸钴（II）的新型催化体系，需氧氧化为它们的氧化产物。已经提出了一种自由基机理来解释这些烃的需氧氧化。该2 /钴（OAC）2催化体系进行了优化，将反应范围进行了探讨。

  DOI：

  10.1002/jhet.3971
• 作为产物：
  描述：

  ethyl 4-bromo-1,6-methano<10>annulene-3-carboxylate 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1,6-methano[10]annulene-3,4-dicarboxylic anhydride
  参考文献：
  名称：

  Synthesis and Emission Properties of 1,6-Methano[10]annulene-3,4-dicarboximides

  摘要：

  A mixture of 1,6-methano[10]annulene-3,4-dicarboximide (le) and 1,6-methano[10]annulene-3,4-dicarboxylic anhydride (3) was obtained through a two-step sequence involving cyanation and subsequent hydrolysis from ethyl 4-bromo-1,6-methano [10]annulene-3-carboxylate (5). Alkylations of le provided If and 1g, and the nucleophilic substitution of p-fluoronitrobenzene with le yielded 1i. Copper-catalyzed arylations of le with arylhalides gave la and 1h. Reactions of 3 with anilines afforded la and 1h. Emission properties of the imides obtained are also reported.

  DOI：

  10.3987/com-11-12135

文献信息

• <scp> <i>N</i> ‐Hydroxy </scp> ‐1,6‐methano[10]annulene‐3,4‐dicarboximide/Co( <scp>OAc</scp> ) ₂ : A novel catalytic system for the aerobic oxidation of alkylarenes
  作者：Shengli Zuo、Jianjun Liu、Ang Zuo

  DOI：10.1002/jhet.3971

  日期：2020.6

  were aerobically oxidized to their oxygenated products via a novel catalytic system using N ‐hydroxy‐1,6‐methano[10]annulene‐3,4‐dicarboximide (2 ) and cobalt(II) acetate under mild conditions. A radical mechanism has been proposed to account for the aerobic oxidation of these hydrocarbons. The 2 /Co(OAc)2 catalytic system was optimized and the reaction scope was explored.

  烷基苯在温和的条件下，通过使用N-羟基-1,6-甲基[10]环戊烯-3,4-二羧酸二亚胺（2）和乙酸钴（II）的新型催化体系，需氧氧化为它们的氧化产物。已经提出了一种自由基机理来解释这些烃的需氧氧化。该2 /钴（OAC）2催化体系进行了优化，将反应范围进行了探讨。
• Synthesis and Emission Properties of 1,6-Methano[10]annulene-3,4-dicarboximides
  作者：Shigeyasu Kuroda、Mitsunori Oda、Naoko Tamura、Ryuta Miyatake、Naoko Matsumoto、Yoshikazu Horino、Daisuke Miyawaki

  DOI：10.3987/com-11-12135

  日期：——

  A mixture of 1,6-methano[10]annulene-3,4-dicarboximide (le) and 1,6-methano[10]annulene-3,4-dicarboxylic anhydride (3) was obtained through a two-step sequence involving cyanation and subsequent hydrolysis from ethyl 4-bromo-1,6-methano [10]annulene-3-carboxylate (5). Alkylations of le provided If and 1g, and the nucleophilic substitution of p-fluoronitrobenzene with le yielded 1i. Copper-catalyzed arylations of le with arylhalides gave la and 1h. Reactions of 3 with anilines afforded la and 1h. Emission properties of the imides obtained are also reported.