1,3,5-trimethyl-2-phenethylbenzene | 143425-74-5

• 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: 1,3,5-trimethyl-2-phenethylbenzene
• 英文别名: 1,3,5-Trimethyl-2-(2-phenylethyl)benzene
• CAS: 143425-74-5
• 化学式: C₁₇H₂₀
• 分子量: 224.346
• InChiKey: MTUCPIFPHNFZEH-UHFFFAOYSA-N

物化性质

• 熔点：
  38-39 °C
• 沸点：
  154-160 °C(Press: 5 Torr)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-phenyl-1-(2,4,6-trimethylphenyl)ethanone 在 甲醇 、 copper oxide-chromium oxide 、 硫酸 、 镍 、 甲基环己烷 作用下， 100.0~150.0 ℃ 、13.73 MPa 条件下， 生成 1,3,5-trimethyl-2-phenethylbenzene
  参考文献：
  名称：

  HIGHLY HINDERED STILBENES

  摘要：

  DOI：

  10.1021/jo01189a011

文献信息

• “Bulky-Yet-Flexible” α-Diimine Palladium-Catalyzed Reductive Heck Cross-Coupling: Highly Anti-Markovnikov-Selective Hydroarylation of Alkene in Air
  作者：Xu-Wen Yang、Dong-Hui Li、A-Xiang Song、Feng-Shou Liu

  DOI：10.1021/acs.joc.0c01509

  日期：2020.9.18

  regioselective and efficient reductive Heck reaction, a series of moisture- and air-stable α-diimine palladium precatalysts were rationally designed, readily synthesized, and fully characterized. The relationship between the structures of the palladium complexes and the catalytic properties was investigated. It was revealed that the“bulky-yet-flexible”palladium complexes allowed highly anti-Markovnikov-selective

  为了进行高度区域选择性和高效的还原性Heck反应，合理设计，易于合成和充分表征了一系列湿气和空气稳定的α-二亚胺钯预催化剂。研究了钯配合物的结构与催化性能之间的关系。揭示了“大而尚柔的”钯配合物在好氧条件下可以使烯烃与（杂）芳基溴化物高度抗马尔科夫尼科夫选择性加氢芳基化。本方案的进一步合成应用可以提供对功能和生物活性分子的快速直接访问。
• Development of the Direct Suzuki–Miyaura Cross-Coupling of Primary <i>B</i>-Alkyl MIDA-boronates and Aryl Bromides
  作者：Jeffrey D. St. Denis、Conor C. G. Scully、C. Frank Lee、Andrei K. Yudin

  DOI：10.1021/ol500057a

  日期：2014.3.7

  The development of a palladium-catalyzed sp3–sp2 Suzuki–Miyaura cross-coupling of B-alkyl-N-methyliminodiacetyl (B-alkyl MIDA) boronates and (hetero)aryl bromides is reported. This transformation is tolerant of a variety of functional groups (F, NO2, CN, Cl, COCH3, and CHO). B-Alkyl MIDA boronates allow an efficient cross-coupling reaction directed toward the synthesis of unsymmetrical methylene diaryls

  发展的钯-催化的SP 3 -sp 2铃木-宫浦交叉偶合B-烷基Ñ -methyliminodiacetyl（乙-烷基MIDA）硼酸酯和（杂）芳基溴化物进行报告。这种转化耐受各种官能团（F，NO 2，CN，Cl，COCH 3和CHO）。B-烷基MIDA硼酸酯可实现高效的交叉偶联反应，以高收率或优异收率合成不对称的亚甲基二芳基以及烷基化的芳烃。
• <i>B</i>-Alkyl Suzuki−Miyaura Cross-Coupling Reactions with Air-Stable Potassium Alkyltrifluoroborates
  作者：Gary A. Molander、Chang-Soo Yun、María Ribagorda、Betina Biolatto

  DOI：10.1021/jo0343331

  日期：2003.7.1

  palladium-catalyzed cross-coupling reaction of substituted potassium alkyltrifluoroborates with aryl halides and aryl triflates proceeds readily with moderate to good yields. The potassium alkyltrifluoroborates 1, 2, and 3a-e were easily synthesized and obtained as air-stable crystalline solids that can be stored for long periods of time. All of the cross-couplings proceed under the same reaction conditions using PdCl(2)(dppf)

  取代的烷基三氟硼酸钾与芳基卤化物和芳基三氟甲磺酸酯的钯催化交叉偶联反应易于进行，产率中等至良好。烷基三氟硼酸钾1、2和3a-e易于合成，并以空气稳定的结晶固体形式获得，可以长期保存。所有交叉偶联均在相同的反应条件下使用PdCl（2）（dppf）.CH（2）Cl（2）作为催化剂在THF-H（2）O中在3当量的Cs（2）存在下进行以CO（3）为基。
• Efficient Synthesis of Sterically Hindered Arenes Bearing Acyclic Secondary Alkyl Groups by Suzuki-Miyaura Cross-Couplings
  作者：Chengxi Li、Tianyu Chen、Bowen Li、Guolan Xiao、Wenjun Tang

  DOI：10.1002/anie.201411518

  日期：2015.3.16

  Bulky P,PO ligands were designed to inhibit isomerization and reduction side reactions during the cross coupling between sterically hindered aryl halides and alkylboronic acids. Suzuki–Miyaura cross‐couplings between di‐ortho‐substituted aryl bromides and acyclic secondary alkylboronic acids have been achieved with high yields. The method has also enabled the preparation of ortho‐alkoxy di‐ortho‐substituted

  庞大的P，P = O配体设计用于在位阻芳基卤化物和烷基硼酸之间的交叉偶联过程中抑制异构化和还原副反应。高产率地实现了二邻位取代的芳基溴化物和无环仲烷基硼酸之间的Suzuki-Miyaura交叉偶联。该方法还能够以优异的收率制备带有异丙基的邻烷氧基双邻取代芳烃。合成方法的实用性已在雌酮的后期修饰中以及在向棉酚的新合成途径中的应用中得到了证明。
• Palladium-catalyzed cross-coupling of alkylindium reagent with diaryliodonium salt
  作者：Wen-Xin Li、Bo-Wen Yang、Jin-He Na、Weidong Rao、Xue-Qiang Chu、Zhi-Liang Shen

  DOI：10.1016/j.tetlet.2022.153729

  日期：2022.4

  alkylindium reagents with diaryliodonium salts proceeded efficiently in the presence of tetrakis(triphenylphosphine)palladium [Pd(PPh3)4], 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos), lithium tert-butoxide, and lithium chloride in DMA/THF (1:1) at 100 °C, leading to the corresponding cross-coupling products in moderate to good yield with broad substrate scope and wide functional group tolerance

  在四(三苯基膦)钯[Pd(PPh 3 ) 4 ]、2-二环己基膦基-2',6'-二甲氧基联苯(SPhos)、叔丁基锂的存在下，钯催化的烷基铟试剂与二芳基碘鎓盐的交叉偶联有效地进行-丁醇和氯化锂在 DMA/THF (1:1) 中在 100 °C 下，导致相应的交叉偶联产物具有中等至良好的产率，具有广泛的底物范围和广泛的官能团耐受性。