1-phenyl-2-(2',4',6'-trimethylphenyl)propan-1-one | 84839-90-7

• 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: 1-phenyl-2-(2',4',6'-trimethylphenyl)propan-1-one
• 英文别名: 1-phenyl-2-(2,4,6-trimethyl-phenyl)-propan-1-one；1-phenyl-2-(2,4,6-trimethylphenyl)-propan-1-one；1-phenyl-2-(2,4,6-trimethylphenyl)-1-propanone；1-phenyl-2-(2,4,6-trimethylphenyl)propan-1-one；2-(2,4,6-trimethylphenyl)-1-phenylpropan-1-one；2-mesityl-1-phenylpropan-1-one
• CAS: 84839-90-7
• 化学式: C₁₈H₂₀O
• 分子量: 252.356
• InChiKey: KDGOASRSWKHFSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  79.5-80 °C
• 沸点：
  377.7±11.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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-phenyl-2-(2',4',6'-trimethylphenyl)propan-1-one 以100%的产率得到
  参考文献：
  名称：

  WAGNER, PETER J.;ZHOU, BOLI, TETRAHEDRON LETT., 30,(1989) N0, C. 5389-5392

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三甲基氰苄 在 lithium diisopropyl amide 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 1-phenyl-2-(2',4',6'-trimethylphenyl)propan-1-one
  参考文献：
  名称：

  Wagner, Peter J.; Zhou, Boli; Hasegawa, Tadashi, Journal of the American Chemical Society, 1991, vol. 113, # 25, p. 9640 - 9654

  摘要：

  DOI：

文献信息

• Palladium Complexes of 1,3,5,7-Tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane:  Synthesis, Crystal Structure and Use in the Suzuki and Sonogashira Reactions and the α-Arylation of Ketones
  作者：George Adjabeng、Tim Brenstrum、Christopher S. Frampton、Al J. Robertson、John Hillhouse、James McNulty、Alfredo Capretta

  DOI：10.1021/jo049474x

  日期：2004.7.1

  mantane were prepared and characterized with Pd[1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane]2·dba shown to be an effective catalyst for use in the Suzuki and Sonogashira reactions and the α-arylation of ketones. Couplings using this versatile complex proceeded in excellent yields under mild conditions.

  制备了1,3,5,7-四甲基-2,4,8-三氧杂-6-苯基-6-磷金刚烷的钯配合物并用Pd [1,3,5,7-四甲基-2,4,8进行了表征[-trioxa-6-苯基-6-磷酸金刚烷] 2 ·dba被证明是用于Suzuki和Sonogashira反应以及酮的α-芳基化反应的有效催化剂。使用这种多功能复合物的偶联在温和条件下以优异的产率进行。
• Phosphorinanes as Ligands for Palladium-Catalyzed Cross-Coupling Chemistry
  作者：Tim Brenstrum、Julie Clattenburg、James Britten、Serguei Zavorine、Jeff Dyck、Alan J. Robertson、James McNulty、Alfredo Capretta

  DOI：10.1021/ol052579h

  日期：2006.1.1

  organopalladium cross-coupling chemistry. Prepared via a direct double Michael addition of a monoalkyl- or arylphosphine to phorone followed by a Wolf-Kishner reduction, phosphorinanes are relatively inexpensive to manufacture and allow modification of one of the alkyl moieties permitting steric and electronic fine-tuning of the ligands. Library screening and applications of these ligands in the Suzuki, Sonogashira

  [结构：见正文]磷化氢是一类适用于有机钯交叉偶联化学反应的膦配体。通过将单烷基膦基或芳基膦直接双迈克尔加成到佛酮中，然后进行Wolf-Kishner还原，制备了二膦酸酯，其制造相对便宜，并且允许对烷基部分之一进行修饰，从而可以对配体进行空间和电子微调。介绍了这些配体在Suzuki，Sonogashira，酮芳基化和芳基胺化反应中的文库筛选和应用。
• (IPr)Pd(acac)Cl:  An Easily Synthesized, Efficient, and Versatile Precatalyst for C−N and C−C Bond Formation
  作者：Nicolas Marion、Elise C. Ecarnot、Oscar Navarro、Dino Amoroso、Andrew Bell、Steven P. Nolan

  DOI：10.1021/jo060190h

  日期：2006.5.1

  and IPr·HCl [acac = acetylacetonate; IPr = N,N‘-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, (IPr)Pd(acac)Cl (1), has proven to be a highly active PdII precatalyst in the Buchwald−Hartwig and the α-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.

  从两种市售原料Pd（acac）2和IPr·HCl [acac =乙酰丙酮酸盐；IPr ＝N，已开发出N′-双（2，6-二异丙基苯基）咪唑-2-亚烷基]。所得的络合物（IPr）Pd（acac）Cl（1）已被证明是在Buchwald-Hartwig和α-酮芳基化反应中具有高活性的Pd II预催化剂。已经筛选了多种底物，包括未活化的，位阻的和杂环芳基氯化物。
• Well-Defined, Air-Stable (NHC)Pd(Allyl)Cl (NHC = N-Heterocyclic Carbene) Catalysts for the Arylation of Ketones
  作者：Mihai S. Viciu、Romain F. Germaneau、Steven P. Nolan

  DOI：10.1021/ol026745m

  日期：2002.11.1

  A number of palladium-N-heterocyclic carbene (NHC) complexes were found to be active catalysts for the arylation of ketones. A large number of substrates, both aryl halides and ketones, are compatible with the reaction conditions. The ketone arylation reactions are achieved with low catalyst loading in short reaction times using aryl chlorides and triflates as reactive partners. [reaction: see text]

  发现许多钯-N-杂环卡宾（NHC）配合物是酮芳基化的活性催化剂。大量的底物，芳基卤化物和酮都与反应条件相容。使用芳基氯化物和三氟甲磺酸酯作为反应伙伴，可以在较短的反应时间内以较低的催化剂负载量实现酮芳基化反应。[反应：看文字]
• An efficient and mild protocol for the α-arylation of ketones mediated by an (imidazol-2-ylidene)palladium(acetate) system
  作者：Rohit Singh、Steven P. Nolan

  DOI：10.1016/j.jorganchem.2005.07.083

  日期：2005.12

  complexes has been studied in the α-arylation of ketones. The enolate was generated in situ via use of slight excess of sodium tert-butoxide as base. The results showed a high activity, allowing for the coupling of non-activated chlorides. The use of hindered substrates provided an avenue for convenient synthesis of various ketone derivatives. The first examples of α-arylation of ketones at room temperature

  在酮的α-芳基化中已经研究了定义明确的N-杂环卡宾（NHC）-乙酸钯络合物的活性。烯醇盐是通过使用略微过量的叔丁醇钠作为碱原位生成的。结果显示出高活性，允许偶联未活化的氯化物。受阻底物的使用提供了便利合成各种酮衍生物的途径。还介绍了由NHC连接的催化剂介导的酮在室温下α-芳基化的第一个例子。