1,1'-(1,4-phenylene)bis(butan-1-one) | 100971-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1'-(1,4-phenylene)bis(butan-1-one)
• 英文别名: 1-Butanone, 1,1'-(1,4-phenylene)bis-；1-(4-butanoylphenyl)butan-1-one
• CAS: 100971-82-2
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: AURSILZBIUDQGF-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C
• 沸点：
  355.4±25.0 °C(Predicted)
• 密度：
  0.998±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1'-(1,4-phenylene)bis(butan-1-one) 在 palladium on activated charcoal 高氯酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 80.0 ℃ 、340.0 kPa 条件下， 反应 6.0h， 以76%的产率得到1,4-二-N-丁基苯
  参考文献：
  名称：

  Issac, Yvette A.; El-Zein, S. M.; Barakat, Y., Revue Roumaine de Chimie, 1995, vol. 40, # 5, p. 463 - 470

  摘要：

  DOI：
• 作为产物：
  描述：

  对苯二甲酸二乙酯 在 thorium dioxide 、 丁酸 作用下， 生成 1,1'-(1,4-phenylene)bis(butan-1-one)
  参考文献：
  名称：

  DE951361

  摘要：

  公开号：

文献信息

• Reshuffling of Functionalities Catalyzed by a Ruthenium Complex in Water
  作者：Chao-Jun Li、Dong Wang、Dong-Li Chen

  DOI：10.1021/ja00156a028

  日期：1995.12

  Repositioning the functionalities of olefinic alcohols is a common process encountered in synthesis. Such transformations often require multistep reactions, or strong acids. We report here that, in the presence of a catalytic amount of RuClsub 2}(PPhsub 3})sub 3}, homoallylic alcohols and allyl alcohols undergo structural reorganization in which both the hydroxyl group and the olefin have been reshuffled

  重新定位烯烃醇的官能团是合成中常见的过程。这种转化通常需要多步反应或强酸。我们在此报告说，在催化量的 RuClsub 2}(PPhsub 3})sub 3} 存在下，高烯丙醇和烯丙醇发生结构重组，其中羟基和烯烃均已重新改组. 这些结果表明高烯丙醇改组的速率决定步骤是初始烯烃迁移。不管确切的机制如何，尽管反应仍然仅限于苄基和肉桂基类型的醇，使用催化量的过渡金属络合物在水和空气环境下选择性地重新排列分子结构，在机械和合成方面开辟了许多新的机会。重组前体也可以通过铟介导的巴比尔反应在水中制备，这一事实进一步增强了其合成的多功能性。11 参考，1 图。
• Barbier-type reactions of nitriles and alkyl iodides mediated by samarium(II) iodide in the presence of catalytic nickel(II) iodide
  作者：Han-Young Kang、Sang-Eun Song

  DOI：10.1016/s0040-4039(99)02194-2

  日期：2000.2

  The samarium(II) iodide-mediated intermolecular Barbier-type reactions of nitriles and alkyl iodides have been investigated. In the presence of a catalytic amount of nickel(II) iodide, the reaction proceeded smoothly to provide the corresponding ketones. Amides also reacted to give ketones under the same Barbier-type conditions.

  碘化sa（II）介导的腈和烷基碘的分子间巴比尔型反应已得到研究。在催化量的碘化镍（II）的存在下，反应平稳进行以提供相应的酮。在相同的巴比尔型条件下，酰胺也反应生成酮。
• Rh‐Catalyzed Coupling of Aldehydes with Allylboronates Enables Facile Access to Ketones
  作者：Kezhuo Zhang、Jiaxin Huang、Wanxiang Zhao

  DOI：10.1002/chem.202103851

  日期：2022.3.10

  A novel strategy for the preparation of ketones from aldehydes and allylic boronic esters is presented. This reaction involves the allylation of aldehydes with allylic boronic esters and the Rh-catalyzed chain-walking of homoallylic alcohols. This approach features mild reaction conditions, broad substrate scope, and excellent functional groups. Mechanistic studies also supported that a tandem allylation

  提出了一种由醛和烯丙基硼酸酯制备酮的新策略。该反应涉及醛与烯丙基硼酸酯的烯丙基化和高烯丙基醇的 Rh 催化链行走。该方法具有反应条件温和、底物范围广、官能团优良等特点。机理研究还支持串联烯丙基化和链式行走过程。
• Nickel-Catalyzed Isomerization of Homoallylic Alcohols
  作者：Dustin D. Youmans、Hai N. Tran、Levi M. Stanley

  DOI：10.1021/acs.orglett.3c01201

  日期：2023.5.19

  Nickel-catalyzed isomerizations of homoallylic alcohols and a bishomoallylic alcohol are presented. These isomerization reactions occur in the presence of a simple nickel catalyst that does not require addition of an exogenous ligand. The corresponding ketone products are generated in ≤98% yield.

  提出了镍催化的均烯丙醇和双烯丙醇异构化。这些异构化反应在不需要添加外源配体的简单镍催化剂存在下发生。相应的酮产物的产率≤98%。
• Ruthenium-catalyzed isomerization of homoallylic alcohols in water
  作者：Dong Wang、Dongli Chen、John X. Haberman、Chao-Jun Li

  DOI：10.1016/s0040-4020(98)00252-x

  日期：1998.5

  Through the catalysts of RuCl2(PPh3)(3), the functional groups of homoallylic alcohols are repositioned to give allylic alcohols with controlled regioselectivity. The reaction proceeds most efficiently in an aqueous media. The selectivity in product formation is affected by the reaction temperature and the amount of the catalyst being used. A higher reaction temperature and the use of a smaller amount of the catalyst are preferable for the formation of allylic alcohols. The reaction process was postulated as a tandem olefin migration-allylic rearrangement. Under the same reaction conditions, the functional groups of allylic alcohols undergo allylic rearrangements. (C) 1998 Elsevier Science Ltd. All rights reserved.