1-oxa-3-(1-methylethyl)-5-ethoxy-2,2-diphenyl-2-silacyclopentane | 627878-62-0

• 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: 1-oxa-3-(1-methylethyl)-5-ethoxy-2,2-diphenyl-2-silacyclopentane
• 英文别名: 5-Ethoxy-2,2-diphenyl-3-propan-2-yloxasilolane
• CAS: 627878-62-0
• 化学式: C₂₀H₂₆O₂Si
• 分子量: 326.511
• InChiKey: GDNXNXIZKIMPDK-UHFFFAOYSA-N

物化性质

• 沸点：
  373.8±42.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.56
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxa-3-(1-methylethyl)-5-ethoxy-2,2-diphenyl-2-silacyclopentane 在 potassium fluoride 、 三氟化硼乙醚 、 双氧水 、 potassium hydrogencarbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 7-methyl-1-octene-4,6-diol
  参考文献：
  名称：

  Use of an Aminosilyllithium for the Diastereoselective Synthesis of Diphenyl Oxasilacyclopentane Acetals and Polyols

  摘要：

  The conjugate addition reaction of a stable, in situ generated silyllithium gives a beta-hydroxysilyl ester with high diastereoselectivity. Conversion of the beta-hydroxysilyl ester to a beta-fluorosilyl ester affords the precursor to the oxasilacyclopentane acetal in high yields under mild conditions. A hydride reduction and subsequent intramolecular silylation lead to the acetal in excellent yields. Finally, highly selective nucleophilic substitution affords oxasilacyclopentanes, which undergo a mild oxidation to afford 1,3-trans diols with high selectivity.

  DOI：

  10.1021/ol035577a
• 作为产物：
  描述：

  chloro(N,N-diethylamino)diphenylsilane 在 三氟化硼乙醚 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 5.25h， 生成 1-oxa-3-(1-methylethyl)-5-ethoxy-2,2-diphenyl-2-silacyclopentane
  参考文献：
  名称：

  Use of an Aminosilyllithium for the Diastereoselective Synthesis of Diphenyl Oxasilacyclopentane Acetals and Polyols

  摘要：

  The conjugate addition reaction of a stable, in situ generated silyllithium gives a beta-hydroxysilyl ester with high diastereoselectivity. Conversion of the beta-hydroxysilyl ester to a beta-fluorosilyl ester affords the precursor to the oxasilacyclopentane acetal in high yields under mild conditions. A hydride reduction and subsequent intramolecular silylation lead to the acetal in excellent yields. Finally, highly selective nucleophilic substitution affords oxasilacyclopentanes, which undergo a mild oxidation to afford 1,3-trans diols with high selectivity.

  DOI：

  10.1021/ol035577a

文献信息

• Use of an Aminosilyllithium for the Diastereoselective Synthesis of Diphenyl Oxasilacyclopentane Acetals and Polyols
  作者：Jason M. Tenenbaum、K. A. Woerpel

  DOI：10.1021/ol035577a

  日期：2003.11.1

  The conjugate addition reaction of a stable, in situ generated silyllithium gives a beta-hydroxysilyl ester with high diastereoselectivity. Conversion of the beta-hydroxysilyl ester to a beta-fluorosilyl ester affords the precursor to the oxasilacyclopentane acetal in high yields under mild conditions. A hydride reduction and subsequent intramolecular silylation lead to the acetal in excellent yields. Finally, highly selective nucleophilic substitution affords oxasilacyclopentanes, which undergo a mild oxidation to afford 1,3-trans diols with high selectivity.