(E)-2-Ethyl-1-iodo-1-(trimethylsilyl)-1-hexene | 88315-75-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-Ethyl-1-iodo-1-(trimethylsilyl)-1-hexene
• 英文别名: [(E)-2-ethyl-1-iodohex-1-enyl]-trimethylsilane
• CAS: 88315-75-7
• 化学式: C₁₁H₂₃ISi
• 分子量: 310.294
• InChiKey: FYJZXPMRNMLVBI-KHPPLWFESA-N

物化性质

• 沸点：
  269.8±23.0 °C(Predicted)
• 密度：
  1.203±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.15
• 重原子数：
  13.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  (E)-2-Ethyl-1-iodo-1-(trimethylsilyl)-1-hexene 、 异氰酸苯酯 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到(Z)-3-Ethyl-2-trimethylsilanyl-hept-2-enoic acid phenylamide
  参考文献：
  名称：

  Charge-directed conjugate addition reactions of silylated .alpha.,.beta.-unsaturated amidate anions

  摘要：

  A variety of N-substituted alpha-silylated-alpha,beta-unsaturated amidate anions (2) have been found to be excellent Michael acceptors in charge-directed conjugate addition reactions with Grignard and organolithium reagents. The effects of olefin substitution, Si-substitution, N-substitution, and amidate counterion have been studied. Anionic acceptors may be prepared in situ by the addition of silylated vinyllithium reagents to isocyanates and then allowed to undergo conjugate addition reactions with subsequently added nucleophiles, but it was found to be more efficient to isolate neutral acceptors and regenerate the acceptor anion through the use of excess nucleophile. Beta-Substituted acceptors were found to react only with reactive organolithium reagents while a beta,beta-disubstituted acceptor failed to undergo conjugate addition reactions. A primary amide acceptor (14d) also undergoes addition reactions with larger quantitites of nucleophiles suggesting that dianionic amidate acceptors (31) are involved. Diene acceptor 24 was found to undergo a 1,6-addition reaction with n-BuLi. Sodium and potassium amidate salts were found to be inferior to lithium and magnesium salts in addition reactions in keeping with the expectation that an increase in carbonyl-group charge burden retards conjugate reactions. Triphenylsilyl-containing acceptor 16 was found to be more reactive in reactions with n-BuMgCl but less reactive with bulkier tert-BuMgCl. Adduct dianions can be monoalkylated with alkyl iodides and used in Peterson olefination reactions.

  DOI：

  10.1021/jo00078a028
• 作为产物：
  描述：

  1-三甲基硅烷-1-己炔 在 N-碘代丁二酰亚胺 、 titanocene dichloride 、 氯化二乙基铝 作用下， 生成 (E)-2-Ethyl-1-iodo-1-(trimethylsilyl)-1-hexene
  参考文献：
  名称：

  A highly stereoselective synthesis of 1-halo-1-(trimethylsilyl)-2,2-dialkyl olefins

  摘要：

  DOI：

  10.1021/jo00178a037

文献信息

• MILLER, R. B.;AL-HASSAN, MOHAMMED, I., J. ORG. CHEM., 1984, 49, N 4, 725-726
  作者：MILLER, R. B.、AL-HASSAN, MOHAMMED, I.

  DOI：——

  日期：——