2-(4-chlorophenyl)-3-phenyl-1H-inden-1-one | 3312-36-5

• 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-chlorophenyl)-3-phenyl-1H-inden-1-one
• 英文别名: 2-p-chlorophenyl-3-phenylindenone；2-(4-Chlor-phenyl)-3-phenyl-indon；2-(4-Chlor-phenyl)-3-penyl-indon；2-p-Chlorphenyl-3-phenyl-indenon；2-(4-Chlorophenyl)-3-phenylinden-1-one
• CAS: 3312-36-5
• 化学式: C₂₁H₁₃ClO
• 分子量: 316.787
• InChiKey: FTFNYLRAKCIRHT-UHFFFAOYSA-N

物化性质

• 沸点：
  469.9±45.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• 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：

  2-(4-chlorophenyl)-3-phenyl-1H-inden-1-one 、 甲基碘化镁 生成 2-(4-chlorophenyl)-7-methyl-3-phenyl-1H-indene
  参考文献：
  名称：

  MIURA, MASAHIRO;NOJIMA, MASATOMO;KUSABAYASHI, SHIGEKAZU;MCCULLOUGH, K. J., J. AMER. CHEM. SOC., 1984, 106, N 10, 2932-2936

  摘要：

  DOI：
• 作为产物：
  描述：

  {2-[(4-chlorophenyl)ethynyl]phenyl}(phenyl)methanone 在 水 、 碘 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以70%的产率得到2-(4-chlorophenyl)-3-phenyl-1H-inden-1-one
  参考文献：
  名称：

  碘介导的邻炔基芳基酮环化合成茚酮衍生物

  摘要：

  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。

  DOI：

  10.1002/ejoc.201700968

文献信息

• Synthesis of Indenones Via Palladium-Catalyzed Carbonylation with Mo(CO)₆ as a CO Surrogate
  作者：Dong-Kun Li、Bo Zhang、Qi Ye、Wei Deng、Zheng-Yang Xu

  DOI：10.1021/acs.organomet.1c00693

  日期：2022.2.28

  of safety and operability, Mo(CO)6 was introduced into the reaction as a carbonyl source. Mechanistic investigations suggested that the reaction proceeded through sequential oxidative addition, alkyne insertion, carbonyl insertion, and reductive elimination steps to produce the observed carbonylation indenone products. Moreover, the indenones obtained with Mo(CO)6 as a CO surrogate can be functionalized

  炔烃的过渡金属催化羰基化已成为合成茚酮化合物的强大引擎。在此，我们报道了一种有效的 Pd 催化的邻溴芳基碘化物与炔烃的无配体羰基化反应，以提供茚酮化合物。该协议允许邻溴芳基碘化物和炔烃上的广泛官能团，从而产生羰基化产物。此外，考虑到安全性和可操作性的因素，Mo(CO) 6作为羰基源被引入反应中。机理研究表明，该反应通过顺序氧化加成、炔烃插入、羰基插入和还原消除步骤进行，以产生观察到的羰基化茚酮产物。此外，以Mo(CO) 6作为CO 替代物获得的茚酮可以通过对环境友好的方式被官能化以形成合成有用的衍生物。
• Photoinduced C–C bond cleavage for the synthesis of 2,4-disubstituted-1-naphthols from indenone derivatives and sulfoxonium ylide
  作者：Prapas Khorphueng、Jumreang Tummatorn、Wacharakorn Patumanon、Charnsak Thongsornkleeb、Sukit Chonradeenitchakul、Somsak Ruchirawat

  DOI：10.1039/d2ob00958g

  日期：——

  The synthesis of 2,4-disubstituted-1-naphthols has been developed employing photomediated C–C bond cleavage (UV-LED 390 nm) of cyclopropane fused-indanones generated in situ from the reaction between indenones and trimethylsulfoxonium chloride under basic conditions at room temperature. Seventeen substrates were examined in this study. The results showed that indenone precursors containing aryl substituents

  2,4-二取代-1-萘酚的合成采用光介导的 C-C 键断裂 (UV-LED 390 nm) 由茚酮和三甲基氯化锍在室温下在碱性条件下原位反应生成的环丙烷稠合茚满酮温度。在这项研究中检查了 17 种底物。结果表明，含有芳基取代基的茚酮前体可以顺利提供所需产物，收率高达 81%。
• Cationic and Neutral Pd^II and Pt^II Pincer Complexes of Phosphinamino-Triazolyl-Pyridine [PN(H)N]: Pincer Ligand-Stabilized Palladium Nanoparticles and Their Catalytic Annulation of Internal Alkynes to Indenones
  作者：Sonu Sheokand、Maravanji S. Balakrishna

  DOI：10.1021/acs.inorgchem.3c01273

  日期：2023.8.7

  6-(PPh2)-N(H)(C5H3N)(C2HN3C6H5)}] [1, PN(H)N hereafter], and its palladium and platinum complexes and their catalytic application. The reaction of 1 with [M(COD)Cl2] (M = Pd or Pt) afforded the cationic complex [(MCl)PN(H)N}-κ3-P,N,N]Cl [M = Pd (2) or Pt (3)]. Alternatively, compounds 2 and 3 were also synthesized by treating [2,6-H2N(C5H3N)(C2HN3C6H5)}] (A) with [M(COD)Cl2] (M = Pd or Pt), followed by the addition

  我们描述了基于三唑基-吡啶的氨基膦的合成，N -(二苯基膦基)-6-(1-苯基)-1 H- (1,2,3-三唑-4-基)吡啶-2-胺[2 ,6-(PPh 2 )-N(H)(C 5 H 3 N)(C 2 HN 3 C 6 H 5 )}] [ 1 , PN(H)N 以下] 及其钯和铂络合物和它们的催化应用。1与 [M(COD)Cl 2 ]（M = Pd 或 Pt）反应得到阳离子络合物 [(MCl)PN(H)N}-κ 3 -P,N,N]Cl [M = Pd ( 2 )或Pt( 3 )]。或者，化合物2和3也通过用[M(COD)Cl 2处理[2,6-H 2 N(C 5 H 3 N)(C 2 HN 3 C 6 H 5 )}]( A )来合成]（M = Pd 或 Pt），然后添加化学计量的 PPh 2 Cl 和 Et 3 N。中性脱芳构化络合物 [(MCl)PNN}-κ 3 -P,N,N] [M
• Rhodium-Catalyzed Oxidative Decarboxylation Annulation Reactions of Mandelic Acids and Alkynes: An Efficient Synthetic Method for Indenones
  作者：Xiaobo Yu、Yulian Duan、Weijie Guo、Tao Wang、Qingxiao Xie、Shutao Wu、Chenggong Jiang、Zixiong Fan、Jianhui Wang、Guiyan Liu

  DOI：10.1021/acs.organomet.7b00004

  日期：2017.3.13

  Efficient rhodium-catalyzed oxidative decarboxylation annulation reactions between mandelic acids and alkyne derivatives are described. The desired indenone products were obtained in medium to good yields under the optimized reaction conditions, which were a [RhCp*Cl-2](2) catalyst (10.0 mol %) in combination with a PCy3 ligand (10.0 mol %) and AgSbF6 (10 mol %) and Cu(OAc)(2) (20 mol %) additives. Many functional groups are compatible with the reaction under the optimized reaction conditions. This strategy provides a promising method for the construction of indenones from cheap and commercially available starting materials.
• Palladium-Catalyzed Annulation of Alkynes with <i>Ortho</i>-Halide-Containing Benzyl Alcohols in Aqueous Medium
  作者：Jie Feng、Guoping Lu、Meifang Lv、Chun Cai

  DOI：10.1021/jo501444g

  日期：2014.11.7

  The Pd-catalyzed annulations of ortho-halide-containing benzyl alcohols with alkynes for the synthesis of indenones were achieved in aqueous Triton X-100 micelles with good yields and wide substrate scopes. Moreover, the indenones obtained in this procedure can be further functionalized to form some more synthetic useful derivatives via an environmental-friendly way.