苯基{4-[(三甲基硅烷基)甲基]苯基}甲酮 | 1983-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯基{4-[(三甲基硅烷基)甲基]苯基}甲酮
• 英文名称: phenyl{4-[(trimethylsilyl)methyl]phenyl}methanone
• 英文别名: 4-(trimethylsilylmethyl)benzophenone；p-trimethylsilylmethylbenzophenone；4-(trimethylsilanyl-methyl)-benzophenone；4-(Trimethylsilyl-methyl)-benzophenon；4-Trimethylsilylmethyl-benzophenon；Phenyl-[4-(trimethylsilylmethyl)phenyl]methanone
• CAS: 1983-50-2
• 化学式: C₁₇H₂₀OSi
• 分子量: 268.431
• InChiKey: RGABWMFCXACXQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2931900090

反应信息

• 作为产物：
  描述：

  碘甲基三甲基硅烷 、 4-碘二苯酮 在 1,1,3,3-四甲基脲 、 锌 、 1,1'-双(二苯基膦)二茂铁 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 反应 48.0h， 以95%的产率得到苯基{4-[(三甲基硅烷基)甲基]苯基}甲酮
  参考文献：
  名称：

  Synthesis of Functionalized Benzylsilanes from Arylzinc Compounds and (Iodomethyl)trimethylsilane by Means of a Novel Rh Catalysis

  摘要：

  [GRAPHICS]The catalytic activity of a Rh complex in cross-coupling between ArZnI and TMSCH2I was examined in which the Rh complex, generated in situ from [RhCl(1,5-cyclooctadiene)](2) and 1,1'-bis(diphenylphosphino)ferrocene, exhibited excellent catalytic activity for the production of various functionalized benzylsilanes in good yields. From P-31 NMR studies of various solutions containing several of the reaction components, confirmation of the rapid and quantitative transfer of aryl groups from ArZnI to the Rh complex to form arylrhodium species was ascertained. A catalytic cycle, commencing with the transmetalation, was thus proposed for the reaction.

  DOI：

  10.1021/jo0520994

文献信息

• <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。
• Palladium-catalyzed arylation of polar organometallics mediated by 9-methoxy-9-borabicyclo[3.3.1]nonane: Suzuki reactions of extended scope
  作者：Alois Fürstner、Günter Seidel

  DOI：10.1016/0040-4020(95)00677-z

  日期：1995.10

  organometallic reagent RM, and not as usually from a borane and a base. This approach allows cross couplings of aryl halides with e.g. alkynyl-, methyl-, or TMSCH2-groups, which were beyond the scope of the conventional Suzuki reaction. The method is highly chemoselective and turned out to be compatible with aldehyde-, amide-, ketone-, ester- and cyano functions as well as with basic nitrogen atoms

  提出了进行铃木反应的另一种方法。由9-甲氧基-9-硼双环[3.3.1]壬烷（9-OMe-9-BBN）和极性有机金属试剂RM制备这些钯催化的CC键形成中实际的亲核试剂所必需的硼酸盐，而不是通常从硼烷和碱中提取。该方法允许芳基卤化物与例如炔基，甲基或TMSCH 2-基交叉偶联，这超出了常规的Suzuki反应的范围。该方法具有高度的化学选择性，并且与醛，酰胺，酮，酯和氰基官能团以及底物中的碱性氮原子兼容。它被用于合成炔属天然产物朱尼普尔（9a）和奥替平甲基醚（10）。自从11 B NMR研究表明，9-OMe-9-BBN仅用作传递RM试剂的穿梭物，但在反应过程中保持不变，因此有可能将第一个亚化学计量的Suzuki型反应装置硼。该“催化”方案用于制备化合物8，该化合物因其化学发光特性而非常有价值。
• Friedel–Crafts acetylation and benzoylation of benzylsilanes and xanthenes
  作者：Vasilios Georgakilas、Gerasimos P. Perdikomatis、Anastasios S. Triantafyllou、Michael G. Siskos、Antonios K. Zarkadis

  DOI：10.1016/s0040-4020(02)00114-x

  日期：2002.3

  Ph; Me, H, Me; Me, Me, Me; Ph, H, H; Ph, H, Ph; Ph, H, Me; Ph, Me, Me), xanthenes (3-benzoyl and 3,6-dibenzoyl), and 9-Me3Si-xanthenes (3-benzoyl, 3,6-dibenzoyl, 3-acetyl and 3,6-diacetyl) using Friedel–Crafts reactions and typical Lewis acid catalysts (AlCl3, FeCl3, ZnCl2) is described. Desilylation side reactions caused by AlCl3 become significant in substrates with weak carbon–silicon bonds (e.g.

  各种苄基硅烷（p -R 1 CO–C 6 H 4 –CR 2 R 3 –SiMe 3：R 1，R 2，R 3 = Me，H，H; Me的对乙酰基和对苯甲酰基衍生物的合成，H，Ph; Me，H，Me; Me，Me，Me; Ph，H，H; Ph，H，Ph; Ph，H，Me; Ph，Me，Me），黄嘌呤（3-苯甲酰基和3，使用Friedel-Crafts反应和典型的路易斯酸催化剂（AlCl 3，FeCl 3）形成6-二苯甲酰基）和9-Me 3的硅氧杂蒽（3-苯甲酰基，3,6-二苯甲酰基，3-乙酰基和3,6-二乙酰基），氯化锌2）进行了说明。由AlCl 3引起的脱甲硅烷基化副反应在碳-硅键弱的基材（例如Ph 2 CH-SiMe 3）中变得很明显，在Ph 3 C-SiMe 3的情况下，仅分离出了脱甲硅烷基化产物Ph 3 CH。
• Petrow et al., Doklady Akademii Nauk SSSR, 1955, vol. 100, p. 929,931
  作者：Petrow et al.

  DOI：——

  日期：——
• Synthesis of Functionalized Benzylsilanes from Arylzinc Compounds and (Iodomethyl)trimethylsilane by Means of a Novel Rh Catalysis
  作者：Hideki Takahashi、Kabir M. Hossain、Yasushi Nishihara、Takanori Shibata、Kentaro Takagi

  DOI：10.1021/jo0520994

  日期：2006.1.1

  [GRAPHICS]The catalytic activity of a Rh complex in cross-coupling between ArZnI and TMSCH2I was examined in which the Rh complex, generated in situ from [RhCl(1,5-cyclooctadiene)](2) and 1,1'-bis(diphenylphosphino)ferrocene, exhibited excellent catalytic activity for the production of various functionalized benzylsilanes in good yields. From P-31 NMR studies of various solutions containing several of the reaction components, confirmation of the rapid and quantitative transfer of aryl groups from ArZnI to the Rh complex to form arylrhodium species was ascertained. A catalytic cycle, commencing with the transmetalation, was thus proposed for the reaction.