2-(2-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl)-2-propen-1-OL | 204335-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl)-2-propen-1-OL
• 英文别名: 4-[tert-butyl(dimethyl)silyl]oxy-2-methylidene-3-phenylbutan-1-ol
• CAS: 204335-03-5
• 化学式: C₁₇H₂₈O₂Si
• 分子量: 292.494
• InChiKey: UOCRXWBPJVEYGN-UHFFFAOYSA-N

物化性质

• 沸点：
  358.290±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.956±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.34
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl)-2-propen-1-OL 在 indium 、 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 1.0h， 生成 1-cyclohexyl-3-methylidene-4-phenylpentane-1,5-diol
  参考文献：
  名称：

  Effective 1,4-Asymmetric C−C/C−O Stereoinduction in Indium-Promoted Coupling Reactions of Aldehydes to Protected and Unprotected [1-(Bromomethyl)vinyl] Alkanols. The Status of Intramolecular Chelation within Functionalized Allylindium Reagents

  摘要：

  The stereochemistry of the coupling reactions of oxygen-substituted bromides 8-10 with isobutyraldehyde, benzaldehyde, and cyclohexanecarboxaldehyde in water is described. The examples involving the O-silylated derivatives 8 exhibit moderate anti stereoselectivity. In contrast, rather high (most often in excess of 80:20) syn diastereofacial bias is observed when hydroxy bromides 10 are involved. Consequently, stereocontrolled 1,4-asymmetric induction under aqueous conditions can be realized in either direction on demand. These results are considered to reflect the fact that the siloxy systems enter into C-C bond formation via conventional Felkin-Anh transition state arrangements. The crossover observed for the unprotected analogues is believed to be a consequence of the preferred adoption of chelated transition states, these interactions likely being fundamental to aqueous organometallic chemistry.

  DOI：

  10.1021/jo9715534
• 作为产物：
  描述：

  Methyl 2-(2-{[tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl)acrylate 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以90%的产率得到2-(2-{[Tert-butyl(dimethyl)silyl]oxy}-1-phenylethyl)-2-propen-1-OL
  参考文献：
  名称：

  Effective 1,4-Asymmetric C−C/C−O Stereoinduction in Indium-Promoted Coupling Reactions of Aldehydes to Protected and Unprotected [1-(Bromomethyl)vinyl] Alkanols. The Status of Intramolecular Chelation within Functionalized Allylindium Reagents

  摘要：

  The stereochemistry of the coupling reactions of oxygen-substituted bromides 8-10 with isobutyraldehyde, benzaldehyde, and cyclohexanecarboxaldehyde in water is described. The examples involving the O-silylated derivatives 8 exhibit moderate anti stereoselectivity. In contrast, rather high (most often in excess of 80:20) syn diastereofacial bias is observed when hydroxy bromides 10 are involved. Consequently, stereocontrolled 1,4-asymmetric induction under aqueous conditions can be realized in either direction on demand. These results are considered to reflect the fact that the siloxy systems enter into C-C bond formation via conventional Felkin-Anh transition state arrangements. The crossover observed for the unprotected analogues is believed to be a consequence of the preferred adoption of chelated transition states, these interactions likely being fundamental to aqueous organometallic chemistry.

  DOI：

  10.1021/jo9715534