(2-(2-phenylethynyl)phenyl)(p-tolyl)methanone

• 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-(2-phenylethynyl)phenyl)(p-tolyl)methanone
• 英文别名: [2-(2-phenylethynyl)phenyl](p-tolyl)methanone；(4-Methylphenyl)-[2-(2-phenylethynyl)phenyl]methanone
• 化学式: C₂₂H₁₆O
• 分子量: 296.368
• InChiKey: PAZKMQXVVIRBKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  (2-(2-phenylethynyl)phenyl)(p-tolyl)methanone 在 水 、 碘 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以83%的产率得到1-[2-(4-methylbenzoyl)phenyl]-2-phenylethane-1,2-dione
  参考文献：
  名称：

  碘/水介导邻炔基芳酰基化合物的氧化及氧化产物在氮杂环合成中的应用

  摘要：

  报道了一种简单的碘/水介导的邻炔基芳酰基化合物三键氧化以提供三羰基化合物。该反应通过在相邻芳酰基的帮助下形成异色烯醇中间体而进行。产物三羰基化合物是通用的合成前体，在用单胺和二胺、肼和氨基醇处理后，可提供各种杂环支架，如异吲哚啉酮、酞嗪、苯并咪唑异喹啉酮、喹喔啉和苯并咪唑-喹喔啉杂化化合物。讨论了上述杂环形成的机理方面。最后，报告了异吲哚啉酮天然产物马兜铃内酰胺 BII 的短合成路线。

  DOI：

  10.1002/ejoc.201300046
• 作为产物：
  描述：

  2-苯基乙炔基苯甲醛 在 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (2-(2-phenylethynyl)phenyl)(p-tolyl)methanone
  参考文献：
  名称：

  Ni-Catalyzed Intramolecular Cycloaddition of Methylenecyclopropanes to Alkynes

  摘要：

  Ni-catalyzed intramolecular cycloaddition of methylenecyclopropanes (MCPs) to arkylalkynes via proximal bond cleavage is reported. The reaction provides a facile route for the preparation of cyclopenta[a]indene derivatives.

  DOI：

  10.1021/ol1028628

文献信息

• 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。
• 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.
• US7582722B1
  申请人：——

  公开号：US7582722B1

  公开（公告）日：2009-09-01
• Ni-Catalyzed Intramolecular Cycloaddition of Methylenecyclopropanes to Alkynes
  作者：Bangben Yao、Yong Li、Zunjun Liang、Yuhong Zhang

  DOI：10.1021/ol1028628

  日期：2011.2.18

  Ni-catalyzed intramolecular cycloaddition of methylenecyclopropanes (MCPs) to arkylalkynes via proximal bond cleavage is reported. The reaction provides a facile route for the preparation of cyclopenta[a]indene derivatives.
• Iodine/Water-Mediated Oxidation of<i>o</i>-Alkynylaroyl Compounds and Application of the Products of Oxidation in the Synthesis of Nitrogen Heterocycles
  作者：Karuppusamy Sakthivel、Kannupal Srinivasan

  DOI：10.1002/ejoc.201300046

  日期：2013.6

  facile iodine/water-mediated oxidation of the triple bond of o-alkynylaroyl compounds to furnish tricarbonyl compounds is reported. The reaction proceeds through the formation of isochromenol intermediates by the assistance of the neighbouring aroyl group. The product tricarbonyl compounds are versatile synthetic precursors that, upon treatment with mono- and diamines, hydrazines and amino alcohols, afford

  报道了一种简单的碘/水介导的邻炔基芳酰基化合物三键氧化以提供三羰基化合物。该反应通过在相邻芳酰基的帮助下形成异色烯醇中间体而进行。产物三羰基化合物是通用的合成前体，在用单胺和二胺、肼和氨基醇处理后，可提供各种杂环支架，如异吲哚啉酮、酞嗪、苯并咪唑异喹啉酮、喹喔啉和苯并咪唑-喹喔啉杂化化合物。讨论了上述杂环形成的机理方面。最后，报告了异吲哚啉酮天然产物马兜铃内酰胺 BII 的短合成路线。