trimethylsilyl ether of 4-oxo-1-pentanol | 108439-45-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: trimethylsilyl ether of 4-oxo-1-pentanol
• 英文别名: 5-[(trimethylsilyl)oxy]pentan-2-one；1-trimethylsiloxy-pentane-4-one；5-trimethylsiloxypentan-2-one；5-trimethylsilyloxypentan-2-one
• CAS: 108439-45-8
• 化学式: C₈H₁₈O₂Si
• 分子量: 174.315
• InChiKey: UFAZQBUFURBDQS-UHFFFAOYSA-N

物化性质

• 沸点：
  64-66 °C(Press: 1 Torr)
• 密度：
  0.872±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trimethylsilyl ether of 4-oxo-1-pentanol 在 正丁基锂 、 1,8-双二甲氨基萘 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 15.67h， 生成 7-chloro-6-methoxy-1-((trimethylsilyl)oxy)decan-4-one
  参考文献：
  名称：

  通过银（I）促进的半缩醛烷基化的对映体合成螺缩醛：头孢菌素E和F的全合成

  摘要：

  已经开发了银（I）促进的分子内半缩醛烷基化，其将容易获得的酮-氯二醇转化为含有5,5-，5,6-和5,7-元环系统的官能化的螺缩醛。此过程的效率在真菌代谢产物头孢菌内酯E和F的简明全合成中得到了证明。

  DOI：

  10.1021/ol302694s
• 作为产物：
  描述：

  三甲基氯硅烷 以7%的产率得到
  参考文献：
  名称：

  ODINOKOV, V. N.;IGNATYUK, V. K.;KRIVONOGOV, V. P.;TOLSTIKOV, G. A., ZH. ORGAN. XIMII, 1986, 22, N 5, 948-952

  摘要：

  DOI：

文献信息

• Single-carbon bridges bys cyclopentadienyl compounds and metallocene complexes thereof
  申请人：Repsol Quimica S.A.

  公开号：US06534665B1

  公开（公告）日：2003-03-18

  The present invention relates to metallocenes, wherein the two cyclopentadienyl rings are connected to each other by a single carbon atom characterized by the following general formula III where each A, equal to or different from each other, is selected from the group consisting of: hydrogen, OR3, NRR4, or SR5; and to compounds of formula IV wherein each B, equal to or different from each other, is selected from the group consisting of: OH, NRH or SH, obtained by hydrolizing the corresponding oxygen, nitrogen or sulfur containing groups from compounds of formula III. These compounds are used as active catalyst components in the polymerization of olefins.

  本发明涉及金属烯烃，其中两个环戊二烯基环通过一个碳原子相互连接，其特征在于以下通用公式III： 其中每个A相同或不同，选自包括氢、OR3、NRR4或SR5的组；以及公式IV的化合物： 其中每个B相同或不同，选自包括OH、NRH或SH的组，通过水解相应含氧、氮或硫的化合物III中的基团而获得。这些化合物用作催化聚合烯烃的活性催化剂组分。
• Identification and Quantification of Aerosol Polar Oxygenated Compounds Bearing Carboxylic or Hydroxyl Groups. 1. Method Development
  作者：M. Jaoui、T. E. Kleindienst、M. Lewandowski、E. O. Edney

  DOI：10.1021/ac049919h

  日期：2004.8.1

  In this study, a new analytical technique was developed for the identification and quantification of multifunctional compounds containing simultaneously at least one hydroxyl or one carboxylic group, or both. This technique is based on derivatizing first the carboxylic group(s) of the multifunctional compound using an alcohol (e.g., methanol, 1-butanol) in the presence of a relatively strong Lewis acid (BF3) as a catalyst. This esterification reaction quickly and quantitatively converts carboxylic acids to their ester forms. The second step is based on silylation of the ester compounds using bis(trimethylsilyl) trifluoroacetamide (BSTFA) as the derivatizing agent. For compounds bearing ketone groups in addition to carboxylic and hydroxyl groups, a third step was used based on PFBHA derivatization of the carbonyls. Different parameters including temperature, reaction time, and effect due to artifacts were optimized. A GC/MS in EI and in methane-CI mode was used for the analysis of these compounds. The new approach was tested on a number of multifunctional compounds. The interpretation of their EI (70 eV) and CI mass spectra shows that critical information is gained leading to unambiguous identification of unknown compounds. For example, when derivatized only with BF3−methanol, their mass spectra comprise primary ions at m/z M•+ + 1, M•+ + 29, and M•+ − 31 for compounds bearing only carboxylic groups and M•+ + 1, M•+ + 29, M•+ − 31, and M+. − 17 for those bearing hydroxyl and carboxylic groups. However, when a second derivatization (BSTFA) was used, compounds bearing hydroxyl and carboxylic groups simultaneously show, in addition to the ions observed before, ions at m/z M•+ + 73, M•+ − 15, M•+ − 59, M•+ − 75, M•+ − 89, and 73. To the best of our knowledge, this technique describes systematically for the first time a method for identifying multifunctional oxygenated compounds containing simultaneously one or more hydroxyl and carboxylic acid groups.

  在本研究中，开发了一种新的分析技术，用于鉴定和定量含有至少一个羟基或一个羧基或两者的多官能团化合物。该技术基于首先使用醇（例如甲醇、1-丁醇）在相对较强的路易斯酸（BF3）催化下对多官能团化合物的羧基进行衍生化。这种酯化反应迅速且定量地将羧酸转化为酯形式。第二步是使用双(三甲基硅基)三氟乙酰胺（BSTFA）作为衍生化剂对酯化合物进行硅烷化。对于除羧基和羟基外还含有酮基的化合物，采用了基于PFBHA对羰基进行衍生化的第三步。优化了包括温度、反应时间和因人工产物引起的影响等多个参数。使用电子轰击源（EI）和甲烷化学电离（CI）模式的气相色谱/质谱法（GC/MS）分析了这些化合物。对多种多官能团化合物测试了新方法。对其EI（70 eV）和CI质谱的解释表明，获得了关键信息，从而能够明确鉴定未知化合物。例如，仅通过BF3−甲醇衍生化时，它们的质谱包含仅含有羧基的化合物的离子m/z M•+ + 1、M•+ + 29和M•+ − 31，以及同时含有羟基和羧基的化合物的离子m/z M•+ + 1、M•+ + 29、M•+ − 31和M•+ − 17。然而，当使用第二步衍生化（BSTFA）时，同时含有羟基和羧基的化合物除了之前观察到的离子外，还显示出m/z M•+ + 73、M•+ − 15、M•+ − 59、M•+ − 75、M•+ − 89和73的离子。据我们所知，这项技术首次系统地描述了一种鉴定同时含有一个或多个羟基和羧酸基团的多官能团含氧化合物的方法。
• Total Synthesis and Configurational Assignment of Ascospiroketal A
  作者：Stanley Chang、Soo Hur、Robert Britton

  DOI：10.1002/chem.201502754

  日期：2015.11.9

  The total synthesis of the marine fungus‐derived natural product ascospiroketal is described. This concise synthesis relies on a unique AgI‐promoted tandem cascade cyclization that provides direct access to the correctly configured tricyclic core of the natural product from a linear precursor. The synthesis of candidate stereostructures of ascospiroketal A allowed for the confident assignment of both

  描述了海洋真菌衍生的天然产物ascospiroketal的全合成。这种简洁的合成方法依赖于独特的Ag I促进的串联级联环化反应，该反应可从线性前体直接进入天然产物的正确配置的三环核。拟螺旋体A候选立体结构的合成使该异常occeptide的相对和绝对立体化学都得到了可靠的分配。
• Odinokov, V. N.; Ignatyuk, V. K.; Krivonogov, V. P., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 5, p. 848 - 851
  作者：Odinokov, V. N.、Ignatyuk, V. K.、Krivonogov, V. P.、Tolstikov, G. A.

  DOI：——

  日期：——
• Enantioselective Synthesis of Spiroacetals via Silver(I)-Promoted Alkylation of Hemiacetals: Total Synthesis of Cephalosporolides E and F
  作者：Stanley Chang、Robert Britton

  DOI：10.1021/ol302694s

  日期：2012.12.7

  A silver(I)-promoted intramolecular hemiacetal alkylation has been developed that converts readily available keto-chlorodiols into functionalized spiroacetals containing 5,5-, 5,6-, and 5,7-membered ring systems. The efficiency of this process is demonstrated in a concise total synthesis of the fungal metabolites cephalosporolides E and F.

  已经开发了银（I）促进的分子内半缩醛烷基化，其将容易获得的酮-氯二醇转化为含有5,5-，5,6-和5,7-元环系统的官能化的螺缩醛。此过程的效率在真菌代谢产物头孢菌内酯E和F的简明全合成中得到了证明。