(E,2R)-3-methyl-4-trimethylsilylbut-3-en-2-ol | 147058-74-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,2R)-3-methyl-4-trimethylsilylbut-3-en-2-ol
• CAS: 147058-74-0
• 化学式: C₈H₁₈OSi
• 分子量: 158.316
• InChiKey: ICPDNULBVMXMNQ-HYDMIIDASA-N

物化性质

• 沸点：
  179.5±15.0 °C(predicted)
• 密度：
  0.843±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E,2R)-3-methyl-4-trimethylsilylbut-3-en-2-ol 在 丙酸 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (E,3R)-4-methyl-3-trimethylsilylhex-4-en-1-ol
  参考文献：
  名称：

  Acyclic diastereoselectivity in the Lewis acid promoted additions of chiral, .beta.-methyl-substituted (E)-crotylsilanes with achiral aldehydes

  摘要：

  The diastereoselection in the Lewis acid promoted addition of chiral, beta-methyl-substituted (E)-crotylsilanes (S)-1a and (R)-1b with alpha-(benzyloxy)acetaldehyde (2) is reversed from syn to anti by changing the Lewis acid from BF3.OEt2 (non-chelation-controlled conditions) to MgBr2.OEt2, a Lewis acid that is capable of forming a strong chelate with the alpha-(benzyloxy) group of the aldehyde. The reactions result in the formation of the syn homoallylic alcohols 3 or the complementary anti products 4.

  DOI：

  10.1021/jo00057a007
• 作为产物：
  描述：

  (E)-2-methyl-2-buten-1-ol 在 4-二甲氨基吡啶 lithium aluminium tetrahydride 、 正丁基锂 、 三氟化硼乙醚 、 叔丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 19.0h， 生成 (E,2R)-3-methyl-4-trimethylsilylbut-3-en-2-ol
  参考文献：
  名称：

  Acyclic diastereoselectivity in the Lewis acid promoted additions of chiral, .beta.-methyl-substituted (E)-crotylsilanes with achiral aldehydes

  摘要：

  The diastereoselection in the Lewis acid promoted addition of chiral, beta-methyl-substituted (E)-crotylsilanes (S)-1a and (R)-1b with alpha-(benzyloxy)acetaldehyde (2) is reversed from syn to anti by changing the Lewis acid from BF3.OEt2 (non-chelation-controlled conditions) to MgBr2.OEt2, a Lewis acid that is capable of forming a strong chelate with the alpha-(benzyloxy) group of the aldehyde. The reactions result in the formation of the syn homoallylic alcohols 3 or the complementary anti products 4.

  DOI：

  10.1021/jo00057a007

文献信息

• Acyclic diastereoselectivity in the Lewis acid promoted additions of chiral, .beta.-methyl-substituted (E)-crotylsilanes with achiral aldehydes
  作者：James S. Panek、Pier F. Cirillo

  DOI：10.1021/jo00057a007

  日期：1993.2

  The diastereoselection in the Lewis acid promoted addition of chiral, beta-methyl-substituted (E)-crotylsilanes (S)-1a and (R)-1b with alpha-(benzyloxy)acetaldehyde (2) is reversed from syn to anti by changing the Lewis acid from BF3.OEt2 (non-chelation-controlled conditions) to MgBr2.OEt2, a Lewis acid that is capable of forming a strong chelate with the alpha-(benzyloxy) group of the aldehyde. The reactions result in the formation of the syn homoallylic alcohols 3 or the complementary anti products 4.