(Z)-4-(triethylsilyloxy)-1-(trimethylsilyl)non-1-ene | 911286-46-9

• 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: (Z)-4-(triethylsilyloxy)-1-(trimethylsilyl)non-1-ene
• 英文别名: triethyl-[(Z)-1-trimethylsilylnon-1-en-4-yl]oxysilane
• CAS: 911286-46-9
• 化学式: C₁₈H₄₀OSi₂
• 分子量: 328.686
• InChiKey: UURRGZRVIYDYKF-VKAVYKQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.78
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (Z)-4-(triethylsilyloxy)-1-(trimethylsilyl)non-1-ene 、 邻苯二甲醛 在 bismuth(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以98%的产率得到cis-2-(6-pentyl-5,6-dihydro-2H-pyran-2-yl)benzaldehyde
  参考文献：
  名称：

  BiBr₃-Initiated Tandem Addition/Silyl-Prins Reactions to 2,6-Disubstituted Dihydropyrans

  摘要：

  A tandem addition/silyl-Prins reaction efficiently affords cis-2,6-disubstituted dihydropyrans (DHPs) using 5 mol % of BiBr3 in CH2Cl2. The reaction occurs between delta-triethyl-silyloxyvinyltrimethylsilanes and a variety of aldehydes to give good to excellent isolated yields of DHPs. The diastereoselectivities in the crude products are significantly affected by aldehyde substitution with electron-rich aldehydes, providing 2-3: 1 (cis: trans) and neutral (or electron-poor) aldehydes affording dr >= 19: 1 (cis: trans).

  DOI：

  10.1021/jo060738k
• 作为产物：
  描述：

  (Z)-1-(trimethylsilyl)non-1-en-4-ol 、 三乙基硅基三氟甲磺酸酯 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(Z)-4-(triethylsilyloxy)-1-(trimethylsilyl)non-1-ene
  参考文献：
  名称：

  BiBr₃-Initiated Tandem Addition/Silyl-Prins Reactions to 2,6-Disubstituted Dihydropyrans

  摘要：

  A tandem addition/silyl-Prins reaction efficiently affords cis-2,6-disubstituted dihydropyrans (DHPs) using 5 mol % of BiBr3 in CH2Cl2. The reaction occurs between delta-triethyl-silyloxyvinyltrimethylsilanes and a variety of aldehydes to give good to excellent isolated yields of DHPs. The diastereoselectivities in the crude products are significantly affected by aldehyde substitution with electron-rich aldehydes, providing 2-3: 1 (cis: trans) and neutral (or electron-poor) aldehydes affording dr >= 19: 1 (cis: trans).

  DOI：

  10.1021/jo060738k

文献信息

• BiBr₃-Initiated Tandem Addition/Silyl-Prins Reactions to 2,6-Disubstituted Dihydropyrans
  作者：Yajing Lian、Robert J. Hinkle

  DOI：10.1021/jo060738k

  日期：2006.9.1

  A tandem addition/silyl-Prins reaction efficiently affords cis-2,6-disubstituted dihydropyrans (DHPs) using 5 mol % of BiBr3 in CH2Cl2. The reaction occurs between delta-triethyl-silyloxyvinyltrimethylsilanes and a variety of aldehydes to give good to excellent isolated yields of DHPs. The diastereoselectivities in the crude products are significantly affected by aldehyde substitution with electron-rich aldehydes, providing 2-3: 1 (cis: trans) and neutral (or electron-poor) aldehydes affording dr >= 19: 1 (cis: trans).