1,5-bis(trimethylsilyl)-3-pentanone | 18053-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-bis(trimethylsilyl)-3-pentanone
• 英文别名: 2,2,8,8-tetramethyl-2,8-disila-nonan-5-one；2,2,8,8-Tetramethyl-2,8-disila-nonan-5-on；1,5-Bis-trimethylsilyl-pentan-3-on；3-Pentanone, 1,5-bis(trimethylsilyl)-；1,5-bis(trimethylsilyl)pentan-3-one
• CAS: 18053-95-7
• 化学式: C₁₁H₂₆OSi₂
• 分子量: 230.498
• InChiKey: OQVPXZQYWKRFHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  103 °C(Press: 7 Torr)
• 密度：
  0.8424 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  4.01
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  1,5-bis(trimethylsilyl)-3-pentanone 在 硫酸 作用下， 生成 2,2,8,8,10,10,16,16-octamethyl-1,9-dioxa-2,8,10,16-tetrasila-cyclohexadecane-5,13-dione
  参考文献：
  名称：

  Aliphatic Organo-functional Siloxanes¹

  摘要：

  DOI：

  10.1021/ja01108a042
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 1,5-bis(trimethylsilyl)-3-pentanone
  参考文献：
  名称：

  Andreew; Kucharskaja, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1958, p. 1397;engl.Ausg.S.1349

  摘要：

  DOI：

文献信息

• Chelation-Assisted C–H and C–C Bond Activation of Allylic Alcohols by a Rh(I) Catalyst under Microwave Irradiation
  作者：Chul-Ho Jun、Chang-Hee Lee

  DOI：10.1055/s-0036-1591697

  日期：2018.4

  Chelation-assisted Rh(I)-catalyzed ketone synthesis from allylic alcohols and alkenes through C–H and C–C bond activations under microwave irradiation was developed. Aldimine is formed via olefin isomerization of allyl alcohol under Rh(I) catalysis and condensation with 2-amino-3-picoline, followed by continuous C–H and C–C bond activations to produce a dialkyl ketone. The addition of piperidine accelerates

  开发了螯合辅助的 Rh(I) 催化的酮，通过微波辐射下的 C-H 和 C-C 键活化，由烯丙醇和烯烃合成。醛亚胺是通过烯丙醇在 Rh(I) 催化下的烯烃异构化和与 2-amino-3-picoline 缩合形成的，然后连续的 C-H 和 C-C 键活化产生二烷基酮。哌啶的加入通过在微波条件下促进醛亚胺的形成来加速反应速率。
• Rhodium(i)-catalyzed one-pot synthesis of dialkyl ketones from methanol and alkenes through directed sp3 C–H bond activation of N-methylamine
  作者：Eun-Ae Jo、Ji-Hyun Lee、Chul-Ho Jun

  DOI：10.1039/b814166e

  日期：——

  The hydroacylation of methanol with alkenes was developed using a catalytic system consisting of Rh(I), 2-amino-4-picoline and benzoic acid; the reaction is speculated to occur by the initial N-methylation of 2-amino-4-picoline with methanol, and the subsequent dehydrogenation of the resulting N-methylamine, followed by double chelation-assisted hydroimination of alkene with the imine to give dialkyl ketones after hydrolysis.

  甲醇与烯类的水合酰化反应是利用由Rh(I)、2-氨基-4-吡啶和苯甲酸组成的催化体系开发的；该反应推测首先通过甲醇对2-氨基-4-吡啶进行N-甲基化，随后对产生的N-甲基胺进行脱氢反应，然后通过双配体辅助的烯类与亚胺的水合亚胺反应，最终在水解后生成二烷基酮。
• Mechanistic and Synthetic Studies of the Addition of Alkyl Aldehydes to Vinylsilanes Catalyzed by Co(I) Complexes
  作者：Christian P. Lenges、Peter S. White、Maurice Brookhart

  DOI：10.1021/ja980610n

  日期：1998.7.1

  The mechanistic details of the cobalt-catalyzed intermolecular hydroacylation reaction have been investigated using kinetic, spectroscopic, and crystallographic methods. The Co(I) bisolefin complex 1, [C5Me5Co(C2H3SiMe3)2], was shown to catalyze the addition of a series of alkyl aldehydes (2a−l) to vinylsilanes to give the corresponding ketones with exclusive anti-Markovnikov selectivity under mild

  已经使用动力学、光谱和晶体学方法研究了钴催化的分子间加氢酰化反应的机理细节。Co(I) 双烯烃配合物 1，[C5Me5Co(C2H3SiMe3)2]，在温和条件下催化一系列烷基醛 (2a-l) 加成到乙烯基硅烷中，得到相应的酮，具有独特的抗马尔可夫尼科夫选择性. 催化循环表现出两种静止状态，复合物 1 和双烷基羰基复合物 [C5Me5Co(CO)(R)(R')], 4a-1 处于平衡状态。动力学研究与低温 NMR 光谱一起建立了催化过程中静止状态之间的敏感平衡，这强烈依赖于底物结构。转换限制步骤被建立为从中间体 4 中还原消除酮。
• Application of Rh(I)-Catalyzed C−H Bond Activation to the Ring Opening of 2-Cycloalkenones in the Presence of Amines
  作者：Chul-Ho Jun、Choong Woon Moon、Sung-Gon Lim、Hyuk Lee

  DOI：10.1021/ol025816e

  日期：2002.5.1

  Herein described is the application of the Rh(1)-catalyzed C-H bond activation to the ring-opening of 2-cycloalkenones in the presence of cyclohexylamine. This reaction includes the C-C double bond cleavage of 2-cycloalkenones through the conjugate addition of cyclohexylamine followed by the retro-Mannich-type fragmentation. The resulting ring-opened intermediates subsequently underwent either chelation-assisted hydroacylation to afford a ring-opened dicarbonyl compound or beta-alkylation via a ring contraction.
• The effect of the trimethylsilylmethyl substituent on ketene cycloadditions
  作者：William T. Brady、Theresa C. Cheng

  DOI：10.1021/jo00424a034

  日期：1977.3