methyl 1-oxo-2,3-diphenyl-1H-indene-5-carboxylate | 1380243-12-8

• 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: methyl 1-oxo-2,3-diphenyl-1H-indene-5-carboxylate
• CAS: 1380243-12-8
• 化学式: C₂₃H₁₆O₃
• 分子量: 340.378
• InChiKey: TUVNADDRWAEMNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  对苯二甲酸单甲酯 在 4-二甲氨基吡啶 、 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 copper diacetate 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 萘烷 为溶剂， 反应 36.0h， 生成 methyl 1-oxo-2,3-diphenyl-1H-indene-5-carboxylate
  参考文献：
  名称：

  Benzimides的铑/铜催化环与内部炔烃：合成茚通过连续的C语言？H和C ？N解理

  摘要：

  加倍：铑（III）/铜（II）系统共催化苯并酰亚胺与内部炔烃的环化反应，以合成茚满（参见方案； Cp * = C 5 Me 5）。该反应涉及到过渡金属-碳键向酰亚胺部分的不常见亲核加成。该新颖的反应提供了从容易获得的苯甲酰亚胺和内部炔烃合成茚满的简便途径。

  DOI：

  10.1002/anie.201200271

文献信息

• Access to Indenones by Rhodium(III)-Catalyzed C–H Annulation of Arylnitrones with Internal Alkynes
  作者：Zisong Qi、Mei Wang、Xingwei Li

  DOI：10.1021/ol4025309

  日期：2013.11

  Under redox-neutral conditions, rhodium(III)-catalyzed C–H annulation of N-tert-butyl-α-arylnitrones with internal alkynes has been realized for the synthesis of indenones under mild conditions. This reaction proceeded in moderate to high yields and with good functional group tolerance.

  下的氧化还原中性条件下，铑（III）催化的C-H环ñ -叔丁基α-arylnitrones与内部炔烃已经实现为茚酮类的温和的条件下合成。该反应以中等至高产率进行并且具有良好的官能团耐受性。
• Synthesis of Indenones through Rhodium(III)-catalyzed [3+2] Annulation Utilizing a Recyclable Carbazolyl Leaving Group
  作者：Shiho Ochiai、Asumi Sakai、Yoshinosuke Usuki、Bubwoong Kang、Tetsuro Shinada、Tetsuya Satoh

  DOI：10.1246/cl.200884

  日期：2021.4.5

  9-benzoylcarbazoles with internal alkynes proceeds efficiently through ortho C–H and C–N bond cleavages. This reaction provides direct access to variously substituted indanone derivatives. The carbazolyl leaving group can be readily recovered and reused for preparing the starting materials. Keywords: annulation; rhodium catalyst; C–H bond cleavage

  铑（III）催化的9-苯甲酰基咔唑与内部炔烃的环状偶联通过邻位C–H和C–N键断裂而有效进行。该反应提供了直接获得各种取代的茚满酮衍生物的途径。咔唑基离去基团可以容易地回收并再用于制备起始原料。关键字：环空；铑催化剂 C–H键裂解
• Green Light Triggered Radical Annulation for the Synthesis of Indenone by Metal‐Free Photocatalysis
  作者：Xing He、Jia‐Qi Ji、Meng‐Yan Zhao、Chun‐Hua Ma、Dan‐Dan Zhang、Gui‐Qing Xu、Qing‐Jie Ding、Zhen‐Wei Cui、Yu‐Qin Jiang

  DOI：10.1002/ejoc.202400579

  日期：——

  An efficient photocatalysis has been developed for the synthesis of indanone using low-energy green light as input energy. This methodology provides a greener avenue to construct indanone through a metal-free photocatalytic radical annulation reaction between α-keto acid and internal alkyne.

  已经开发出一种使用低能绿光作为输入能量合成茚满酮的高效光催化方法。该方法为通过α-酮酸和内炔之间的无金属光催化自由基环化反应构建茚满酮提供了一种更绿色的途径。
• Rhodium-Catalyzed Direct Annulation of Aldehydes with Alkynes Leading to Indenones: Proceeding through <i>in Situ</i> Directing Group Formation and Removal
  作者：Shuyou Chen、Jintao Yu、Yan Jiang、Fan Chen、Jiang Cheng

  DOI：10.1021/ol4021145

  日期：2013.9.20

  The Rh-catalyzed direct annulation of an aldehyde with an alkyne leading to indenone was achieved. The in situ temporal installation of acetylhydrazine enables the annulation of the ortho arene C-H bond with alkynes to form ketone hydrazone. Subsequently, the in situ directing group removal takes place since ketone hydrazone is more susceptible toward hydrolysis than aldehyde hydrazone. Notably, this procedure tolerates a series of functional groups, such as methoxyl, acetylamino, fluoro, trifluoromethyl, methoxycarbonyl, chloro, and bromo groups.