(E)-1-(trimethylsiloxy)-1-decene | 51425-57-1

• 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: (E)-1-(trimethylsiloxy)-1-decene
• 英文别名: Decanal-enol-trimethylsilylether；[(E)-dec-1-enoxy]-trimethylsilane
• CAS: 51425-57-1
• 化学式: C₁₃H₂₈OSi
• 分子量: 228.45
• InChiKey: NKUUPHUFQNDOAW-OUKQBFOZSA-N

物化性质

• 沸点：
  246.4±8.0 °C(Predicted)
• 密度：
  0.819±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-(trimethylsiloxy)-1-decene 在 tris(cetylpyridinium) 12-tungstophosphate 、 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以63%的产率得到壬醛
  参考文献：
  名称：

  Dehomologation of Aldehydes via Oxidative Cleavage of Silyl Enol Ethers with Aqueous Hydrogen Peroxide Catalyzed by Cetylpyridinium Peroxotungstophosphate under Two-Phase Conditions

  摘要：

  Dehomologation of aldehydes has been first successfully achieved via oxidative cleavage of silyl enol ethers, derived from aldehydes and trimethylchlorosilane, using aqueous hydrogen peroxide in the presence of a catalytic amount of peroxotungstophophate (PCWP) under phase-transfer conditions. For instance, the oxidation of 1-[(trimethylsilyl)oxy]-1-octene resulting from octanal and Me3SiCl with 35% H2O2 catalyzed by PCWP in dichloromethane at room temperature afforded the one-carbon shorter aldehyde, heptanal, in 79% yield. A variety of silyl enol ethers were also converted into one-carbon shorter aldehydes in good yields. The oxidation under homogeneous conditions using tert-butyl alcohol gave hydrolysis products such as 2-oxooctanol and octanal. It is of interest that [1-(trimethylsilyl)oxy]-1,10-undecadiene involving an enol moiety and a terminal double bond afforded exclusively 9-decenal, in which the enol moiety was selectively oxidized. A plausible reaction path for the oxidative cleavage of silyl enol ethers by the present system has been suggested from the oxidation results of alpha-[(trimethylsilyl)oxy]styrene.

  DOI：

  10.1021/jo990477x
• 作为产物：
  描述：

  环癸酮 、 lithium 以80%的产率得到
  参考文献：
  名称：

  PI, RAFAEL;FRIEDL, THOMAS;RAGUE, SCHLEYER PAUL VON;KLUSENER, PETER;BRANDS+, J. ORG. CHEM., 52,(1987) N 19, 4299-4303

  摘要：

  DOI：

文献信息

• “<i>Syn-Effect</i>” in the Conversion of (<i>E</i>)-α,β-Unsaturated Esters into the Corresponding β,γ-Unsaturated Esters and Aldehydes into Silyl Enol Ethers
  作者：Samar Kumar Guha、Atsushi Shibayama、Daisuke Abe、Maki Sakaguchi、Yutaka Ukaji、Katsuhiko Inomata

  DOI：10.1246/bcsj.77.2147

  日期：2004.12

  The stereochemistry in the conversion of (E)-α,β-unsaturated esters into the corresponding β,γ-unsaturated esters, and that in the conversion of aldehydes into the silyl enol ethers, were investigated. The Z/E ratios of the resulting β,γ-unsaturated esters and the silyl enol ethers varied according to the γ-substituents of the (E)-α,β-unsaturated esters and the α-substituents of the aldehydes, respectively

  研究了(E)-α,β-不饱和酯转化为相应的β,γ-不饱和酯以及醛转化为甲硅烷基烯醇醚的立体化学。所得β,γ-不饱和酯和甲硅烷基烯醇醚的Z/E比率分别根据(E)-α,β-不饱和酯的γ-取代基和醛的α-取代基而变化。这种现象被“syn-effect”合理化，这可能主要归因于 σ → π* 相互作用和/或 6π-电子同芳香性。
• Reaction of Titanate-Type Aldehyde Enolate with Ketones To Provide 3-Hydroxyaldehydes
  作者：Kentaro Yachi、Hiroshi Shinokubo、Koichiro Oshima

  DOI：10.1021/ja9921975

  日期：1999.10.1
• Comasseto, Joao V.; Silveira, Claudio C., Synthetic Communications, 1986, vol. 16, # 10, p. 1167 - 1172
  作者：Comasseto, Joao V.、Silveira, Claudio C.

  DOI：——

  日期：——
• SAIGO, KAZUHIKO;OKAGAWA, SHUJI;NOHIRA, HIROYUKI, BULL. CHEM. SOC. JAP., 1981, 54, N 11, 3603-3604
  作者：SAIGO, KAZUHIKO、OKAGAWA, SHUJI、NOHIRA, HIROYUKI

  DOI：——

  日期：——
• COMASSETO J. V.; SILVEIRA C. C., SYNTH. COMMUN., 16,(1986) N 10, 1167-1171
  作者：COMASSETO J. V.、 SILVEIRA C. C.

  DOI：——

  日期：——