2-(4-methoxyphenyl)-3-phenyl-1H-inden-1-one | 3312-38-7

• 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: 2-(4-methoxyphenyl)-3-phenyl-1H-inden-1-one
• 英文别名: 2-(p-methoxyphenyl)-3-phenyl-1-indenone；2-(4-methoxyphenyl)-3-phenylinden-1-one
• CAS: 3312-38-7
• 化学式: C₂₂H₁₆O₂
• 分子量: 312.368
• InChiKey: PXHJOMLFEJBYPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-3-phenyl-1H-inden-1-one 在 盐酸 、 mercury dichloride 、 锌 作用下， 生成 2-(4-methoxyphenyl)-3-phenyl-1H-indene
  参考文献：
  名称：

  Sigmatropic rearrangements of 1,1-diarylindenes. Migratory aptitudes of aryl migration in the ground and electronically excited states

  摘要：

  DOI：

  10.1021/jo00318a018
• 作为产物：
  描述：

  2-碘苄醇 在 palladium diacetate 四丁基氯化铵 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 2-(4-methoxyphenyl)-3-phenyl-1H-inden-1-one
  参考文献：
  名称：

  Synthesis of indenones via palladium-catalyzed annulation of internal alkynes

  摘要：

  A number of 2,3-disubstituted 1-indenones have been prepared in fair to good yields by treating o-iodo- or o-bromobenzaldehyde with various internal alkynes in the presence of a palladium catalyst. Synthetically, the methodology provides an especially convenient route to stable hindered indenones containing aryl, silyl, and tert-alkyl groups. The reaction is believed to proceed through a palladium-(IV) intermediate, and the regiochemistry of the reaction is controlled sterically.

  DOI：

  10.1021/jo00069a017

文献信息

• Synthesis of 2,3-disubstituted indenones by cobalt-catalyzed [3+2] annulation of o-methoxycarbonylphenylboronic acid with alkynes
  作者：Mitsuhiro Ueda、Tamami Ueno、Yuki Suyama、Ilhyong Ryu

  DOI：10.1039/c6cc08032d

  日期：——

  Treatment of alkynes with o-methoxycarbonylphenylboronic acid in the presence of a cobalt catalyst resulted in the corresponding 2,3-disubstituted indenones.

  将炔烃与在钴催化剂存在下的o-甲氧羰基苯硼酸反应，得到相应的2,3-二取代的茚酮。
• An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water
  作者：Karu Ramesh、Gedu Satyanarayana

  DOI：10.1002/ejoc.201800591

  日期：2018.8.15

  A one‐pot synthesis of indenones, was presented. The reaction involved palladium catalyzed annulation of ortho‐halobenzaldehydes with internal alkynes. Notably, this process was successful in water as the sole green solvent. Significantly, unlike earlier reports, this protocol showed excellent regioselectivity with unsymmetrical alkylarylacetylenes. Further, the strategy was extended to a one‐pot synthesis

  介绍了茚酮的一锅法合成。该反应涉及钯催化的邻卤苯甲醛与内部炔烃的环化。值得注意的是，这个过程在水作为唯一的绿色溶剂中是成功的。值得注意的是，与之前的报道不同，该方案对不对称的烷基芳基乙炔表现出出色的区域选择性。此外，该策略扩展到新木脂素的一锅合成。
• Cobalt-catalyzed arylation of aldimines via directed C–H bond functionalization: addition of 2-arylpyridines and self-coupling of aromatic aldimines
  作者：Ke Gao、Naohiko Yoshikai

  DOI：10.1039/c2cc31114c

  日期：——

  A cobalt–N-heterocyclic carbene catalyst, in combination with an appropriate Grignard reagent, promotes a chelation-assisted aromatic C–H functionalization reaction via addition to an aromatic aldimine.

  一种钴-N-杂环卡宾催化剂与适当的格里尼亚试剂结合，促进通过添加到芳香醛亚胺的螯合辅助芳香C-H功能化反应。
• Gold-Catalyzed Ammonium Acetate Assisted Cascade Cyclization of 2-Alkynylarylketones
  作者：Maciej E. Domaradzki、Yuhua Long、Zhigang She、Xiaochen Liu、Gan Zhang、Yu Chen

  DOI：10.1021/acs.joc.5b01939

  日期：2015.11.20

  An ammonium acetate assisted gold-catalyzed cascade cyclization reaction of 2-alkynylarylketones is described. Under the reported conditions, a gold-catalyzed intramolecular cyclization of 2-alkynylarylketones takes place through two competing reaction mechanisms—a 5-exo-dig or a 6-endo-dig cyclization—leading to two regioisomeric intermediates: isobenzofuranium or isobenzopyrylium. In the presence

  描述了乙酸铵辅助的金催化的2-炔基芳基酮的级联环化反应。在报道的条件下，金的2-炔基芳基酮的分子内环化反应通过两种竞争的反应机理（5- exo - dig或6 - endo - dig环化）发生，从而产生两种区域异构中间体：异苯并fur或异苯并benzo。在乙酸铵存在下，两种中间体化合物分别进一步重排成2，3-二取代的茚满和1，3-二取代的异喹啉。虽然这两种反应途径经由环化，重排级联进行，金介导的5-外型-挖 该方法是特别值得注意的，因为它提供了2-炔​​基芳基酮的新颖环化方案。
• Iodine-Mediated Cyclization of <i>ortho</i> -Alkynylaryl Ketones for the Synthesis of Indenone Derivatives
  作者：Pennapa Chuangsoongnern、Chareef Surinrach、Jumreang Tummatorn、Charnsak Thongsornkleeb、Somsak Ruchirawat

  DOI：10.1002/ejoc.201700968

  日期：2017.9.15

  A new approach for the synthesis of indenone derivatives using I2-promoted cyclization of ortho-alkynylarylketones has been developed. This method provides a metal-free and convenient route for regioselective synthesis of indenones employing ortho-alkynylarylketones with predefined substituents to obtain indenone products in moderate to good yields.

  已经开发了一种使用邻炔基芳基酮的 I2 促进环化合成茚酮衍生物的新方法。该方法为区域选择性合成茚酮提供了一种无金属且方便的途径，使用具有预定取代基的邻炔基芳基酮以中等至良好的产率获得茚酮产物。