1-([1,1'-biphenyl]-4-yl)-3-phenylprop-2-yn-1-one | 500881-71-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1-([1,1'-biphenyl]-4-yl)-3-phenylprop-2-yn-1-one
• 英文别名: 1-(biphenyl-4-yl)-3-phenylprop-2-yn-1-one；2-Propyn-1-one,1'-biphenyl]-4-yl-3-phenyl-；3-phenyl-1-(4-phenylphenyl)prop-2-yn-1-one
• CAS: 500881-71-0
• 化学式: C₂₁H₁₄O
• 分子量: 282.342
• InChiKey: HNLKGLIGUUBOBH-UHFFFAOYSA-N

物化性质

• 沸点：
  461.4±38.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• 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：

  1-([1,1'-biphenyl]-4-yl)-3-phenylprop-2-yn-1-one 在 正丁基锂 作用下， 反应 0.67h， 生成 2-(2,4-dimethoxyphenyl)-3-phenyl-5-(4-biphenyl)furan
  参考文献：
  名称：

  Optical behaviors of conjugated-chain compounds containing benzene and furan units

  摘要：

  Thirteen conjugated-chain compounds which contain benzene and furan units were prepared, their optical behaviors, including UV-vis absorption coefficient (epsilon), absorption wavelengths (lambda(a)) fluorescence emission wavelengths and quantum yields (0) were measured. Meanwhile, their LUMO and HOMO energy were determined by cyclic voltammetry and their second-order polarizations (beta(xxx)) values were determined by solvatochromic method, respectively. The results showed that this kind of compounds possess a shorter lambda(a) (320-365 nm) and performance a higher (P values, especially for 2aa, 2ab, 2ac and 2bb, their Phi values are all more than 90%. These compounds, except 2db, showed a higher beta(xxx) values in DMSO, especially for 2dc (75.77 x 10(-30) m(5) C-1) and 2dd (83.32 x 10(-30) m(5) C-1), than that 10-methyl-acri done (6.578 x 10(-30) m(5) C-1) or 10-benzylacridone (6.845 x 10(-30) m(5) C-1) in DMSO did, and second harmonic generation value of 10-methylacridone and 10-benzylacridone in powder are, respectively, 1.381 and 1.861 times of that value of urea. The beta(xxx) values and Phi values determined for these compounds in this work were lower than these values which were desired in the original work, this phenomena was explained from their molecular structures. This work confirmed that as these compounds performance shorter lambda(a) and higher Phi values, they could be good blue-color optical materials for some fields, such as OLED materials, two-photo absorption materials, fluorescent dyes. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2006.05.035
• 作为产物：
  描述：

  2,2-dibromostyrene 在 ammonium peroxydisulfate 、 正丁基锂 、 silver(I) acetate 作用下， 以 四氢呋喃 、 正己烷 、 水 、 二甲基亚砜 为溶剂， 反应 5.0h， 生成 1-([1,1'-biphenyl]-4-yl)-3-phenylprop-2-yn-1-one
  参考文献：
  名称：

  银催化的双脱羧自由基炔基化/芳基丙酸与α-酮酸的环化：在温和条件下获得壬酮和黄酮的途径

  摘要：

  壬烷由于其多功能性而成为杂环衍生物的各种有机合成中的重要组成部分，而黄酮是具有广泛生物活性的重要一类天然产物。我们描述了芳基丙酸与α-酮酸的催化双脱羧炔基化反应。以Ag（I）/过硫酸盐为催化体系，可以容易地获得带有各种取代基的有价值的炔酮。邻位羟基取代基的引入α-酮酸的位点使该策略进一步适用于通过异环戊烷以类似的银催化体系以中等到良好的收率构建黄酮衍生物。反应在相对温和的反应条件下进行，并能耐受多种官能团。对照实验表明，两个反应均经历自由基过程。

  DOI：

  10.1002/adsc.201701469

文献信息

• Base-mediated benzannulation of α-cyanocrotonates with ynones: facile synthesis of benzonitriles and fluorenes
  作者：Maneesh Kumar Reddy Singam、Attunuri Nagireddy、Sridhar Reddy Maddi

  DOI：10.1039/d0gc00608d

  日期：——

  Benzonitriles and cyanofluorenes have been rapidly obtained via the [3 + 3] benzannulation of readily available alkynones and α-cyanocrotonates using KO^tBu as the only reagent and EtOH (and CO₂) is the only by-product.

  苯腈和氰基芴已通过易得的炔酮和α-氰基巴豆酸酯的[3 + 3]苯环化反应快速获得，其中唯一试剂为KOtBu，唯一副产物为EtOH（和CO2）。
• Flexible Construction of Functionalized‐Pyrroles under Palladium or Copper Catalysis in the Presence of BF ₃  ⋅ Et ₂ O
  作者：Yin Liu、Teng Liu、Biwei Yan、Kun Wei、Wusheng Guo

  DOI：10.1002/adsc.202101292

  日期：2022.3

  friendly operations with the generation of only water as byproduct. The generality of this protocol is demonstrated by the successful preparation of a range of di-, tri-, tetra- and pentasubstituted pyrroles. This methodology is amenable for the synthesis and derivatization of bioactive compounds.

  我们开发了一种灵活的方法，能够在 BF 3  ⋅ Et 2 O 的存在下，在钯或铜催化下获得高度官能化的吡咯。这种催化方法利用市售胺作为反应伙伴，具有广泛的范围、可扩展和友好的操作仅产生水作为副产品。该协议的普遍性通过一系列二、三、四和五取代吡咯的成功制备得到证明。该方法适用于生物活性化合物的合成和衍生化。
• Palladium-catalyzed concerted [4 + 1] cyclization of prop-2-yn-1-ones and isocyanides
  作者：Yingying Shan、Lei Su、Dianpeng Chen、Min Yang、Wenlin Xie、Guanyinsheng Qiu

  DOI：10.1016/j.cclet.2020.04.041

  日期：2021.1

  Abstract A palladium-catalyzed [4 + 1] cycloaddition of prop-2-yn-1-ones with double isocyanides is developed herein. The transformation worked well to produce a series of 2-amino-4-cyanofurans with high efficiency and a broad reaction scope. Based on mechanism studies, it is believed that the palladium-catalyzed [4 + 1] imidoylative cycloaddition of prop-2-yn-1-ones was concerted. Treated with aryl

  摘要本文研究了丙-2-炔-1-酮与双异氰酸酯的钯催化[4 +1]环加成反应。该转化很好地生产了一系列高效且反应范围广的2-氨基-4-氰呋喃。基于机理研究，据信prop-2-yn-1-one的钯催化的[4 +1]酰亚胺化环加成反应是一致的。用芳基胺和H2O处理后，丙-2-炔-1-酮与双异氰酸酯的[4 +1]环加成反应有效地提供了2-氨基-4-酰胺基吡咯。
• Metal-Free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
  作者：Cassandra Taylor、Yuri Bolshan

  DOI：10.1021/ol403370t

  日期：2014.1.17

  A straightforward method for the preparation of ynones from acyl chlorides and potassium alkynyltrifluoroborate salts has been developed. The one-pot reaction proceeds rapidly in the presence of a Lewis acid without exclusion of air and moisture.

  已经开发了一种从酰氯和炔基三氟硼酸钾盐制备炔酮的直接方法。在路易斯酸存在下，一锅法反应迅速进行，并且不排除空气和湿气。
• Recyclable heterogeneous palladium-catalyzed carbonylative Sonogashira coupling under CO gas-free conditions
  作者：Zebiao Zhou、Jianying Li、Zhaotao Xu、Mingzhong Cai

  DOI：10.1080/00397911.2020.1762092

  日期：2020.7.2

  Abstract A convenient, efficient and practical heterogeneous palladium-catalyzed carbonylative Sonogashira coupling of aryl iodides with terminal alkynes under CO gas-free conditions has been developed by using an MCM-41-supported bidentate phosphine palladium acetate complex as catalyst. Here, formic acid was used as the CO source with dicyclohexylcarbodiimide (DCC) as the activator and a wide variety

  摘要 以MCM-41负载的双齿膦乙酸钯配合物为催化剂，开发了一种方便、高效、实用的多相钯催化羰基化Sonogashira偶联芳基碘与末端炔烃在无CO气体条件下的反应。在这里，甲酸用作 CO 源，二环己基碳二亚胺 (DCC) 作为活化剂，并以中等至高产率生成了多种炔基酮。这种多相钯催化剂可以通过简单的过滤过程轻松回收，最多可循环使用 8 次，而不会明显降低活性。图形概要