5-Brom-2-ethyl-1-trimethylsilyloxy-1-penten | 63334-02-1

• 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: 5-Brom-2-ethyl-1-trimethylsilyloxy-1-penten
• 英文别名: [(5-Bromo-2-ethylpent-1-en-1-yl)oxy](trimethyl)silane；(5-bromo-2-ethylpent-1-enoxy)-trimethylsilane
• CAS: 63334-02-1
• 化学式: C₁₀H₂₁BrOSi
• 分子量: 265.266
• InChiKey: HRZLGCLFPANZSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-ethyl-4-pentenal dimethyl acetal 在 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-Brom-2-ethyl-1-trimethylsilyloxy-1-penten
  参考文献：
  名称：

  通过甲硅烷基烯醇醚的分子内曼尼希反应对天然长春胺进行新的对映选择性全合成。

  摘要：

  AbstractNatural Vincamine (1) has been synthesized in an enantioselective manner starting from the ethylpentenal7. In the key step a mixture of the diastereoisomeric racemates,14and15, was directly obtained from the silyl enol ether11and the dihydro‐β‐carboline12by the way of an intramolecularMannichreaction of the intermediate13(Scheme 4). The undesired stereoisomers,14and15b, were recycled to15ausing the related reversibleMannichreaction18 ⇄ 14 + 15, followed by crystallization of the salt from15aand (+)malic acid.15awas converted to natural vincamine (1) in several steps including the known transformation20→1.

  DOI：

  10.1002/hlca.19770600533

文献信息

• A New Enantioselective Total Synthesis of Natural Vincamine<i>via</i>an Intramolecular<i>Mannich</i>Reaction of an Silyl Enol Ether
  作者：Wolfgang Oppolzer、Hartmut Hauth、Paul Pfäffli、Roland Wenger

  DOI：10.1002/hlca.19770600533

  日期：1977.7.13

  AbstractNatural Vincamine (1) has been synthesized in an enantioselective manner starting from the ethylpentenal7. In the key step a mixture of the diastereoisomeric racemates,14and15, was directly obtained from the silyl enol ether11and the dihydro‐β‐carboline12by the way of an intramolecularMannichreaction of the intermediate13(Scheme 4). The undesired stereoisomers,14and15b, were recycled to15ausing the related reversibleMannichreaction18 ⇄ 14 + 15, followed by crystallization of the salt from15aand (+)malic acid.15awas converted to natural vincamine (1) in several steps including the known transformation20→1.