2-hydroxy-4-methyl-1,2-diphenyl-pent-4-en-1-one | 53684-09-6

• 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-hydroxy-4-methyl-1,2-diphenyl-pent-4-en-1-one
• 英文别名: 2-Hydroxy-4-methyl-1,2-diphenylpent-4-en-1-one
• CAS: 53684-09-6
• 化学式: C₁₈H₁₈O₂
• 分子量: 266.34
• InChiKey: LDEVDXUKGYHIEH-UHFFFAOYSA-N

物化性质

• 熔点：
  89-92 °C
• 沸点：
  428.1±33.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-hydroxy-4-methyl-1,2-diphenyl-pent-4-en-1-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 4-methyl-1,2-diphenylcyclohex-4-ene-1,2-diol
  参考文献：
  名称：

  闭环复分解方法合成邻三联苯衍生物

  摘要：

  据报道，使用闭环复分解（RCM）作为关键步骤，从苯甲醚合成邻-叔苯基的方法。合成了具有卤素取代基的邻-三联苯，可以通过交叉偶联反应将其进一步官能化。联苯撑的合成证明了该方法的合成效用。

  DOI：

  10.1002/ejoc.201900988
• 作为产物：
  描述：

  2-甲基-2-丙烯基乙酸酯 、 安息香精油 在 bis(η3-allyl-μ-chloropalladium(II)) 、 potassium hydride 、 二氢二苯磷苯基-4-异丙恶唑 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到2-hydroxy-4-methyl-1,2-diphenyl-pent-4-en-1-one
  参考文献：
  名称：

  Palladium-Catalyzed C-Allylation of Benzoins and an NHC-Catalyzed Three Component Coupling Derived Thereof: Compatibility of NHC- and Pd-Catalysts

  摘要：

  A large range of benzoins was successfully applied as C-nucleophiles in the palladium-catalyzed allylic alkylation with several allyl acetates, resulting in functionalized tertiary homoallylic alcohols. A number of unsymmetrical benzoins can be coupled with high levels of regio- and chemoselectivity. Finally, the challenging compatibility of free N-heterocyclic carbenes with a palladium catalyst has been utilized in a number of metal- and organocatalyzed three-component coupling reactions.

  DOI：

  10.1021/ol801644f

文献信息

• Efficient and sustainable one‐pot synthesis of α‐carbonyl homoallylic alcohols from benzaldehyde and allylic alcohols using both NHC and nickel catalysts
  作者：Yasmina Homrani、Bouchaib Mouhsine、Aurélien Béthegnies、Mohamed Amin El Amrani、Abdallah Karim、Isabelle Suisse、Mathieu Sauthier

  DOI：10.1002/cctc.202300038

  日期：——

  Tandem catalysis: α-carbonyl homoallylic alcohols are synthesized thanks to a tandem reaction that combines the benzoin condensation of aldehydes (synthesis of α-hydroxyketones) promoted by 1,3-dimethylimidazolium chloride/DBU system and the nickel-catalyzed allylic alkylation with allylic alcohol.

  串联催化：α-羰基高烯丙醇是通过串联反应合成的，该反应结合了由 1,3-二甲基咪唑氯化物/DBU 系统促进的醛的安息香缩合（α-羟基酮的合成）和镍催化的烯丙基烷基化与烯丙醇.
• Photoinduced Platinum-Catalyzed Reductive Allylation of α-Diketones with Allylic Carbonates
  作者：Junpei Shimosato、Masaya Sawamura、Yusuke Masuda

  DOI：10.1021/acs.orglett.4c00091

  日期：2024.3.15

  A unique process for the photoinduced platinum-catalyzed reductive allylation of α-diketones with allylic carbonates has been developed. This allylation reaction was found to proceed selectively at the more electron-deficient carbonyl group of the diketone to afford an α-keto homoallylic alcohol. Such products could be further derivatized by transformation of the remaining carbonyl group. A mechanistic

  已经开发出一种独特的光诱导铂催化 α-二酮与烯丙碳酸酯还原烯丙基化的方法。发现这种烯丙基化反应选择性地在二酮的缺电子羰基上进行，得到α-酮高烯丙醇。此类产物可以通过剩余羰基的转化进一步衍生。机理研究表明，光照射产生的羰基自由基与（π-烯丙基）铂络合物反应形成 C-C 键。
• Reaction of .pi.-allylnickel bromide complexes with ketones and aldehydes. Synthesis of .alpha.-methylene-.gamma.-butyrolactones
  作者：L. S. Hegedus、S. D. Wagner、E. L. Waterman、K. Siirala-Hansen

  DOI：10.1021/jo00893a012

  日期：1975.3
• First examples of hypervalent enhancement of photoallylation by allylsilicon compounds via photoinduced electron transfer
  作者：Yutaka Nishigaichi、Akira Suzuki、Takahiro Saito、Akio Takuwa

  DOI：10.1016/j.tetlet.2005.05.124

  日期：2005.8

  Hypervalency (pentacoordination) of silicon atom enhanced photoallylation of 1,2-diketones with allylsilicon reagents, while normal tetracoordinated ones could not. This reaction seems to proceed via photoinduced electron transfer from the silicon reagent to the photoexcited ketone judged from its reactivity and selectivity. (c) 2005 Elsevier Ltd. All rights reserved.
• INDIUM-MEDIATED ALLYLATION OF 1,2-DIKETONES
  作者：Suk-Ku Kang、Tae-Gon Baik、Xiang-Hua Jiao

  DOI：10.1081/scc-120001511

  日期：2002.1.1

  Indium-mediated allylation of 1,2-dicarbonyl compounds with indium and allylic bromides was achieved in the presence of nBu(4)NI or NH4Cl as additive to afford mono- and/or diallylated products in good yields.