(Z)-7-(tetrahydropyranyloxy)-3-<(trimethylsilyl)methyl>-2-methyl-3-hepten-2-ol | 97592-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (Z)-7-(tetrahydropyranyloxy)-3-<(trimethylsilyl)methyl>-2-methyl-3-hepten-2-ol
• 英文别名: (Z)-7-(tetrahydropyranyloxy)-3-[(trimethylsilyl)methyl]-2-methyl-3-hepten-2-ol；(Z)-2-methyl-7-(oxan-2-yloxy)-3-(trimethylsilylmethyl)hept-3-en-2-ol
• CAS: 97592-14-8
• 化学式: C₁₇H₃₄O₃Si
• 分子量: 314.541
• InChiKey: SXDIKIDZCDBHTL-XNTDXEJSSA-N

物化性质

• 沸点：
  403.3±45.0 °C(predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  21.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-四氢吡喃基氧基-丁烷-1-醇 在 三乙烯二胺 、 N-氯代丁二酰亚胺 、 copper(l) iodide 、 二甲基硫 、 三氯硅烷 、 sodium acetate 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 191.5h， 生成 (Z)-7-(tetrahydropyranyloxy)-3-<(trimethylsilyl)methyl>-2-methyl-3-hepten-2-ol
  参考文献：
  名称：

  DABCO-catalyzed coupling of aldehydes with activated double bonds. 4. Stereoselective synthesis of trisubstituted olefins and terpenoid building blocks via 2-(hydroxyalkyl)-2-propenoic esters

  摘要：

  DOI：

  10.1021/jo00220a034

文献信息

• Radical Cyclization of Bromomethyldimethylsilyl Propargyl Ethers; a General Method for the Stereoselective Synthesis of Variously Substituted Trimethylenemethane (TMM) Precursors
  作者：Stéphane Bogen、Michel Journet、Max Malacria

  DOI：10.1080/00397919408011720

  日期：1994.5

  Abstract The radical cyclization of bromomethyldimethylsilyl propargyl ethers allows the regio- and stereoselective preparation of variously substituted 2-trimethylsilylmethyl-2-propen-1-ol derivatives in good yields. After acetylation of the alcohol function, these compounds are useful precursors of trimethylene-methane (TMM) in [3+2] cycloaddition reactions using the Trost methodology.

  摘要 溴甲基二甲基甲硅烷基炔丙基醚的自由基环化允许以良好的产率区域和立体选择性地制备各种取代的 2-三甲基甲硅烷基甲基-2-丙烯-1-醇衍生物。在醇官能团乙酰化后，这些化合物在使用 Trost 方法的 [3+2] 环加成反应中是三亚甲基甲烷 (TMM) 的有用前体。
• Radical cyclization of (bromomethyl)dimethylsilyl propargyl ethers. Regio-, chemo- and stereoselectivity.
  作者：Michel Journet、Max Malacria

  DOI：10.1021/jo00037a026

  日期：1992.5

  Radical cyclization of (bromomethyl)dimethylsilyl propargyl ether derivatives 1 is a powerful reaction with a high degree of regio-, chemo-, and stereoselectivity. Trisubstituted olefins 3, cyclopentene derivatives 5, and diquinane system 7j are obtained in good yields by a judicious choice of unsaturated substituents. Triquinane frameworks could be obtained stereoselectively from a suitable acyclic substrate of type 1 in a one-pot reaction. First attempts have not yet allowed us to aim at this goal due to interesting (1,5) hydrogen transfers. Moreover, we have intercepted, for the first time, the alpha-cyclopropyl radical which is involved in the Stork-Beckwith mechanism of the 5-versus 6-membered ring formation in the vinyl radical cyclization.
• Bogen Stephane, Journet Michel, Malacria Max, Synth. Commun., 24 (1994) N 9, S 1215-1221
  作者：Bogen Stephane, Journet Michel, Malacria Max

  DOI：——

  日期：——
• HOFFMANN, H. M. R.;RABE, J., J. ORG. CHEM., 1985, 50, N 20, 3849-3859
  作者：HOFFMANN, H. M. R.、RABE, J.

  DOI：——

  日期：——