3-(4-methylphenyl)indenone | 22303-76-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 3-(4-methylphenyl)indenone
• 英文别名: 3-(4-Methylphenyl)inden-1-one
• CAS: 22303-76-0
• 化学式: C₁₆H₁₂O
• 分子量: 220.271
• InChiKey: ZVEUODRPSNHMCR-UHFFFAOYSA-N

物化性质

• 熔点：
  54-56 °C(Solv: methanol (67-56-1); dichloromethane (75-09-2))
• 沸点：
  369.5±42.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  3-(4-methylphenyl)indenone 在 氟磺酸 作用下， 生成 [3-(4-methylphenyl)-2H-inden-3-ylium-1-ylidene]oxidanium
  参考文献：
  名称：

  Chemistry of 3-arylindenones: behavior in superacids and photodimerization

  摘要：

  In superacids HSO3F and CF3SO3H, it has been found that 3-arylindenones are very stable and exist as a doubly protonated species. NMR showed protonation both at the oxygen of the carbonyl group and at the C2 carbon of the indenone system. 3-Arylindenones proved however very sensitive to heat and light. Their [2 + 2] photodimerization under daylight has been studied. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.110
• 作为产物：
  描述：

  1-苯基-3-(4-甲基苯基)丙-2-炔-1-酮 在 三氟甲磺酸 、 五氟化锑 作用下， 反应 0.5h， 以75%的产率得到3-(4-methylphenyl)indenone
  参考文献：
  名称：

  Protonation and cyclization of 1,3-diarylpropynones in superacids

  摘要：

  1,3-二芳基丙炔酮 ArC≡CCOAr′ 在酸度范围 H 0 从 -20 到 -14 的超酸中发生质子化，形成稳定的 ArC≡CC(O+H)Ar′ 离子，或在聚炔 C2 原子处质子化，生成反应性 ArC+=CHCOAr′ 物种。讨论了 Ar 和 Ar′ 取代基及反应条件对 ArC+=CHCOAr′ 内分子环化成 3-芳基茚-1-酮的影响。

  DOI：

  10.1007/s11178-005-0097-y

文献信息

• Chemistry of 1,3-diarylpropynones in superacids
  作者：A. V. Vasilyev、S. Walspurger、M. Haouas、J. Sommer、P. Pale、A. P. Rudenko

  DOI：10.1039/b412323a

  日期：——

  In superacids with H0 = −14 to −20, it has been found that 1,3-diarylpropynones ArCCCOAr′ are either protonated on oxygen of carbonyl groups with the formation of stable ions ArCCC(O+H)Ar′ or undergo further transformations when the highly conjugated system is electron-rich enough. In the latter case, 3-arylindenones are produced very rapidly and with high efficiency (up to 95% yield in less than 30 min). The influence of the substituents Ar, Ar′ and of the reaction conditions on the behavior of 1,3-diarylpropynones and on the intramolecular cyclisation have been studied. From the collected data, a mechanism has been proposed involving vinyl cations ArC+=CHCOAr′ and/or dications ArC+=CHC(O+H)Ar′.

  在pH值为−14至−20的超酸中，发现1,3-二芳基丙炔酮ArCCCOAr′可以通过羰基氧的质子化形成稳定的离子ArCCC(O+H)Ar′，或者当高度共轭体系的电子丰富时发生进一步转化。在后者的情况下，3-芳基茚酮非常迅速且高效地生成（在不到30分钟内产率可达95%）。对取代基Ar、Ar′和反应条件对1,3-二芳基丙炔酮行为以及分子内环化的影响进行了研究。根据收集的数据，提出了一种机制，涉及乙烯基阳离子ArC+=CHCOAr′和/或二阳离子ArC+=CHC(O+H)Ar′。
• Ir-catalyzed asymmetric hydrogenation of 3-arylindenones for the synthesis of chiral 3-arylindanones
  作者：Jun Yan、Yu Nie、Feng Gao、Qianjia Yuan、Fang Xie、Wanbin Zhang

  DOI：10.1016/j.tet.2021.132003

  日期：2021.3

  An efficient synthesis of chiral 3-arylindanones via iridium-catalyzed asymmetric hydrogenation of 3-arylindenones has been developed. The reaction showed good compatibility with various functional groups, delivering a variety of 3-arylindanones in excellent yields and with good enantioselectivities. The reaction was also carried out on a gram-scale, delivering the product in quantitative yield. In

  已经开发了通过铱催化的3-炔烃的不对称氢化的有效合成手性3-芳基茚满酮。该反应显示出与各种官能团的良好相容性，以优异的产率和良好的对映选择性提供了各种3-芳基茚满酮。该反应也以克为单位进行，以定量产率递送产物。此外，产品可以轻松衍生化并转化为天然产品和药物制剂。
• Stereoselective Photodimerization of 3-Arylindenones in Solution and in the Solid State
  作者：Naohiro Uemura、Hiroki Ishikawa、Naoki Tamura、Yasushi Yoshida、Takashi Mino、Yoshio Kasashima、Masami Sakamoto

  DOI：10.1021/acs.joc.7b03147

  日期：2018.2.16

  Photodimerization of 3-arylindenones in solution and in the solid state was examined. Irradiation of 3-arylindenones in benzene exclusively gave C2-symmetric anti-HH cyclobutane dimers in good yields. In contrast, photolysis in the solid state afforded syn-HH cyclobutane dimers efficiently, which was considerably influenced by the molecular arrangement in the crystal lattice.

  考察了溶液中和固态的3-炔烃的光二聚化。在苯中辐射3-炔基萘仅以良好的收率得到C 2对称的抗-HH环丁烷二聚体。相反，固态的光解有效地提供了顺式-HH环丁烷二聚体，这在很大程度上受到晶格中分子排列的影响。
• A new, fast and efficient synthesis of 3-aryl indenones: intramolecular cyclization of 1,3-diarylpropynones in superacids
  作者：Aleksander V Vasilyev、Stéphane Walspurger、Patrick Pale、Jean Sommer

  DOI：10.1016/j.tetlet.2004.03.026

  日期：2004.4

  1,3-Diarylpropynones were cleanly converted to the corresponding 3-arylindenones in various superacidic media. This new. simple. one-pot reaction proved to be efficient (yields up to 95%) and very fast (reaction time less than 30 min). (C) 2004 Elsevier Ltd. All rights reserved.
• [2 + 2]-Photodimerization of 3-Arylindenones
  作者：A. V. Vasil’ev、S. Walspurger、P. Pale、J. Sommer

  DOI：10.1007/s11178-005-0214-y

  日期：2005.4