1-(9-p-tolylanthracen-10-yl)butan-1-one

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 1-(9-p-tolylanthracen-10-yl)butan-1-one
• 英文别名: 1-[10-(4-Methylphenyl)anthracen-9-yl]butan-1-one；1-[10-(4-methylphenyl)anthracen-9-yl]butan-1-one
• 化学式: C₂₅H₂₂O
• 分子量: 338.449
• InChiKey: HNKLYILRMQWMJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (2-(pent-1-ynyl)phenyl)(p-tolyl)methanone 、 邻氨基苯甲酸 在 亚硝酸异戊酯 、 三氯乙酸 、 gold(I) chloride 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以87%的产率得到1-(9-p-tolylanthracen-10-yl)butan-1-one
  参考文献：
  名称：

  AuCl催化邻炔基（氧代）苯与苯炔之间的[4 + 2]苯环化。

  摘要：

  [结构：见正文]在温和的条件下，AuCl催化邻炔基（氧代）苯与2-重氮苯重氮的苯环合反应，可制得各种在9位具有酮基的蒽衍生物。高产。该反应最可能通过苯并与苯并吡啶鎓金酸酯配合物之间的[4 + 2]环加成而进行，这是由金诱导的邻炔基（氧代）苯的亲电环化反应生成的。

  DOI：

  10.1021/ol062268m

文献信息

• AuCl-catalyzed reaction of ortho-alkynyl(oxo)benzene with benzenediazonium 2-carboxylate as a synthetic method towards anthracene, triptycene, and phthalazine derivatives
  作者：Kenichiro Sato、Menggenbateer、Toshihiko Kubota、Naoki Asao

  DOI：10.1016/j.tet.2007.10.083

  日期：2008.1

  The AuCl-catalyzed benzannulation of ortho-alkynylphenyl ketones with benzenediazonium 2-carboxylate proceeded efficiently at 40 degrees C in (CH2Cl)(2) and a variety of anthracene derivatives, having a ketone group at 9-position, were produced in good to high yields. On the other hand, the reaction of ortho-alkynylbenzaldehydes with benzenediazonium 2-carboxylate afforded triptycyl ketones. The reactions most probably proceed through the formation of a zwitterionic intermediate by the gold-induced electrophilic cyclization of ortho-alkynyl(oxo)benzenes, followed by the cycloaddition of benzyne. In contrast, when the above reaction was carried out at rt in 1,4-dioxane, phthalazine derivative was produced without the generation of benzyne. (c) 2007 Elsevier Ltd. All rights reserved.
• AuCl-Catalyzed [4+2] Benzannulation between <i>o</i>-Alkynyl(oxo)benzene and Benzyne
  作者：Naoki Asao、Kenichiro Sato

  DOI：10.1021/ol062268m

  日期：2006.11.9

  AuCl-catalyzed benzannulation of o-alkynyl(oxo)benzenes with benzenediazonium 2-carboxylate proceeds under mild conditions and a variety of anthracene derivatives, having a ketone group at the 9-position, are produced in good to high yields. The reaction proceeds most probably through the [4+2] cycloaddition between benzyne and benzopyrylium auric ate complex, which would be generated by the gold-induced electrophilic

  [结构：见正文]在温和的条件下，AuCl催化邻炔基（氧代）苯与2-重氮苯重氮的苯环合反应，可制得各种在9位具有酮基的蒽衍生物。高产。该反应最可能通过苯并与苯并吡啶鎓金酸酯配合物之间的[4 + 2]环加成而进行，这是由金诱导的邻炔基（氧代）苯的亲电环化反应生成的。