苯基-(10-苯基蒽-9-基)甲酮 | 24451-63-6

• 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
• 中文名称: 苯基-(10-苯基蒽-9-基)甲酮
• 英文名称: (phenyl)(9-phenylanthracen-10-yl)methanone
• 英文别名: Phenyl(10-phenylanthracen-9-yl)methanone；phenyl-(10-phenylanthracen-9-yl)methanone
• CAS: 24451-63-6
• 化学式: C₂₇H₁₈O
• 分子量: 358.439
• InChiKey: BTLWICYKBSLCSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  苯基-(10-苯基蒽-9-基)甲酮 在 lithium aluminium tetrahydride 、 乙醚 、 硫酸 作用下， 生成 methyl-[phenyl-(10-phenyl-[9]anthryl)-methyl]-ether
  参考文献：
  名称：

  Conjugated Systems. VI. 1,5-Anionotropic Shifts in the Anthracene Series

  摘要：

  DOI：

  10.1021/ja01174a047
• 作为产物：
  描述：

  蒽酮 在 二硫化碳 、 三氯化铝 、 乙醚 作用下， 生成 苯基-(10-苯基蒽-9-基)甲酮
  参考文献：
  名称：

  Cook, Journal of the Chemical Society, 1926, p. 2171

  摘要：

  DOI：

文献信息

• Substituent Effects on Regioselectivity in the Photorearrangement of a Few Naphthobarrelenes 1
  作者：Meledathu C Sajimon、Danaboyina Ramaiah、S Ajaya Kumar、Nigam P Rath、Manapurathu V George

  DOI：10.1016/s0040-4020(00)00450-6

  日期：2000.7

  The photorearrangement of a few 9,10-disubstituted-naphthobarrelenes to the corresponding naphthosemibullvalenes has been examined. It was observed that the regioselectivity in these photoisomerizations depends on the relative stabilities of the diradical intermediates. AM1 semi-empirical calculations are in support of this view. Thermal transformation of the naphthosemibullvalenes gave the corresponding

  已经研究了一些9,10-二取代的萘桶型烯与相应的萘半球形半价戊烯的光重排。观察到在这些光异构化中的区域选择性取决于双自由基中间体的相对稳定性。AM1半经验计算支持该观点。萘半牛戊烯的热转化以几乎定量的产率得到了相应的加水的萘并萘并呋喃。
• Reactions of cupric halides with organic compounds—V
  作者：S. Gibson、A.D. Mosnaim、D.C. Nonhebel、J.A. Russell

  DOI：10.1016/s0040-4020(01)83252-x

  日期：1969.1

  9-Aryl-10-methylanthracenes undergo reaction with cupric halides to give the corresponding 9-aryl-10-halogenomethylanthracenes. 9-Ethyl- and 9-benzyl-10-methylanthracenes similarly undergo reaction at the Me group rather than at the Et or Bz groups to form the halogenomethyl compound. These results indicate that the 9-alkyl-10-anthrylmethyl radical is more stable than the radicals which would be formed

  9-芳基-10-甲基蒽与卤化铜反应，得到相应的9-芳基-10-卤代甲基蒽。9-乙基和9-苄基-10-甲基蒽同样在Me基上而不是在Et或Bz基上反应形成卤代甲基化合物。这些结果表明9-烷基-10-蒽甲基比通过从Et或Bz基团夺氢形成的自由基更稳定。这些反应还得到其中烷基被卤素取代的产物。这些结果的机械解释是先进的。还检查了9-烷基（或芳基）10-甲基蒽与N-溴琥珀酰亚胺的反应。
• 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。
• Nojima,M. et al., Journal of the Chemical Society. Perkin transactions I, 1978, p. 488 - 495
  作者：Nojima,M. et al.

  DOI：——

  日期：——
• 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.