4-cyano-4'-methoxydibenzoylmethane | 934604-52-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-cyano-4'-methoxydibenzoylmethane
• 英文别名: 4-(3-(4-methoxyphenyl)-3-oxopropanoyl)benzonitrile；4-[3-(4-Methoxyphenyl)-3-oxopropanoyl]benzonitrile；4-[3-(4-methoxyphenyl)-3-oxopropanoyl]benzonitrile
• CAS: 934604-52-1
• 化学式: C₁₇H₁₃NO₃
• 分子量: 279.295
• InChiKey: HYYMBEPHYWURKU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-cyano-4'-methoxydibenzoylmethane 在 三氟乙酸 palladium on activated charcoal 、 二苯基二硒醚 、 氢气 、 peroxodisulfate ion 、 肼 作用下， 反应 2.0h， 生成 endo-2,3-diaza-10,10-dimethoxy-1-(4'-cyanophenyl)-4-(4'-methoxyphenyl)tricyclo[5.2.1.5,9]dec-2-ene
  参考文献：
  名称：

  On the Electronic Character of Localized Singlet 2,2-Dimethoxycyclopentane-1,3-diyl Diradicals:  Substituent Effects on the Lifetime

  摘要：

  Photodenitrogenation of the diazenes 4 affords exclusively the housanes 5 through intramolecular cyclization of the spectrally detected and characterized singlet diradicals 3. The lifetime of singlet diradical 3, determined by transient absorption measurements, depends on the Y and Z substituents at the para position of the phenyl ring and has the following order: Y, Z = OMe, OMe > OMe, CN > CN, CN > OMe, H > Cl, Cl approximately CN, H approximately Me, Me > H, H. This unprecedented substituent effect reveals stabilization of the singlet 2,2-dimethoxycyclopentane-1,3-diyl diradicals 3 through radical, zwitterionic, pi-bonding, and hyperconjugative structures.

  DOI：

  10.1021/ja026301l
• 作为产物：
  描述：

  对氰基苯甲酸甲酯 、 对甲氧基苯乙酮 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 4-cyano-4'-methoxydibenzoylmethane
  参考文献：
  名称：

  Electronic effects in the reaction of 1,3-diaryl-1,3-diketones with hydrazinopyridines

  摘要：

  The regioselectivity of the condensation of electronically unsymmetrical 1,3-diaryl- 1,3-diketones with 2-hydrazinopyridine and 2,6-bis-hydrazinopyridine to form N-(2-pyridyl)-3,5-diarylpyrazoles was studied. Significant electronic effects on regioselectivities were observed, and regioselectivities were opposite to those exhibited by perfluoroalkyl/alkyl 1,3-diketones. The electronic effects correlate well to the difference between the Hammett sigma(+) coefficients of the para substituents on the aryl rings. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.104

文献信息

• Iron‐Catalyzed and Air‐Mediated C( <i>sp</i> ³ )−H Phosphorylation of 1,3‐Dicarbonyl Compounds Involving C−C Bond Cleavage
  作者：Yingcong Ou、Yuanting Huang、Yu Liu、Yanping Huo、Yang Gao、Xianwei Li、Qian Chen

  DOI：10.1002/adsc.202001020

  日期：2020.12.22

  A C(sp3)−H phosphorylation has been achieved via the iron‐catalyzed cross‐coupling reactions between 1,3‐dicarbonyl compounds and P(O)−H compounds involving C−C bond cleavages with air as the oxidant. This transformation provides a straightforward way to construct C(sp3)−P bonds, leading to the formation of β‐ketophosphine oxides in up to 93% yield with good functional group tolerance.

  AC（sp 3）-H磷酸化是通过1,3-二羰基化合物与P（O）-H化合物之间的铁催化交叉偶联反应实现的，其中C-C键的裂解以空气为氧化剂。这种转变为构建C（sp 3）-P键提供了一种直接的方法，导致以高达93％的产率形成β-酮膦氧化物，并具有良好的官能团耐受性。
• The perfluoroalkylthiolation/decarbonylation reaction of 1,3-diketones with perfluoroalkanesulfenic acids
  作者：Jia-Hui Li、Min Jiang、Jin-Tao Liu

  DOI：10.1039/d3ob01482g

  日期：——

  The perfluoroalkylthiolation/decarbonylation reactions of 1,3-dicarbonyl compounds with in situ formed perfluoroalkanesulfenic acids were achieved. Using trifluoromethanesulfonic acid as an additive, a series of α-perfluoroalkylthiolated arylethanones were obtained in moderate to good yields. A possible mechanism was proposed based on the reaction results and control experiments.

  实现了1,3-二羰基化合物与原位形成的全氟烷磺酸的全氟烷基硫基化/脱羰反应。使用三氟甲磺酸作为添加剂，以中等至良好的收率获得了一系列α-全氟烷基硫醇化芳基乙酮。根据反应结果和对照实验提出了可能的机理。