(S)-2,6-di-iso-propyl-1-trimethylsiloxy-1-cyclohexene

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-2,6-di-iso-propyl-1-trimethylsiloxy-1-cyclohexene
• 英文别名: (S)-2,6-Di-isopropyl-1-trimethylsiloxy-1-cyclohexene；[(6S)-2,6-di(propan-2-yl)cyclohexen-1-yl]oxy-trimethylsilane
• 化学式: C₁₅H₃₀OSi
• 分子量: 254.488
• InChiKey: UMYNKMONXUQRNB-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  丙泊酚 在 镍 六甲基磷酰三胺 、 bis{(R)-N-benzyl-α-methylbenzylamido}magnesium 、 氢气 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， -40.0~104.0 ℃ 、10.94 MPa 条件下， 反应 46.0h， 生成 (S)-2,6-di-iso-propyl-1-trimethylsiloxy-1-cyclohexene
  参考文献：
  名称：

  Magnesium amide base-mediated enantioselective deprotonation processes

  摘要：

  A novel homochiral magnesium bisamide has been readily prepared and, following careful optimisation, this species has been shown to react efficiently with a series of prochiral 4-substituted cyclohexanones in the presence of TMSCl to give the corresponding silyl enol ethers in enantiomeric ratios of up to 95:5. Additionally, the same chiral base system has been shown to be highly effective in the desymmetrisation of cis-2,6-disubstituted cyclohexanones, providing excellent levels of both conversion and enantioselection (up to >99.5:0.5 er). Furthermore, the magnesium bisamide has also been shown to mediate a kinetic resolution process with the corresponding trans-disubstituted substrates, allowing access to enantioenriched enol ethers and ketones. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00364-2

文献信息

• Enantioselective deprotonation reactions using polymer-supported chiral magnesium amide bases
  作者：Kenneth W. Henderson、William J. Kerr、Jennifer H. Moir

  DOI：10.1039/b104417f

  日期：——

  Novel and readily accessible polymer-supported chiral magnesium amide reagents have been prepared and shown to be effective in the asymmetric deprotonation of a series of prochiral cyclohexanones, affording good to excellent levels of both conversion and enantiomeric ratio (up to 93:7); the Merrifield-based chiral amine species has been shown to be readily recyclable.

  已经制备了新型且容易获得的聚合物负载的手性镁酰胺试剂，并显示出其在一系列前手性环己酮的不对称去质子化方面有效，可提供良好的转化率和对映体比率（至93：7）。已证明基于Merrifield的手性胺物种易于回收。
• Enantioselective Deprotonation of 2,6-Disubstituted Cyclohexanones with a Homochiral Magnesium Amide Base and the Observation of a Novel Kinetic Resolution Process
  作者：Kenneth W. Henderson、William J. Kerr、Jennifer H. Moir

  DOI：10.1055/s-2001-16048

  日期：——

  A recently developed homochiral magnesium amide base has been shown to be highly effective in the asymmetric deprotonation of cis-2,6-disubstituted cyclohexanones, affording excellent levels of both conversion and enantioselection (up to > 99.5 : 0.5 e.r.). In addition, a novel kinetic resolution process has been realised with the corresponding trans-disubstituted substrates, allowing access to optically enriched enol ethers and chiral ketones.

  最近开发的同手性镁酰胺基在顺式-2,6-二取代环己酮的不对称去质子化过程中非常有效，提供了极好的转化率和对映体选择性（达到 > 99.5 : 0.5 e.r.）。此外，还利用相应的反式二取代底物实现了一种新的动力学解析过程，从而获得了光学富集的烯醇醚和手性酮。