(3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhex-5-en-1-ol | 1196532-16-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhex-5-en-1-ol
• 英文别名: (3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-methylhex-5-enoic acid
• CAS: 1196532-16-7
• 化学式: C₁₃H₂₆O₃Si
• 分子量: 258.433
• InChiKey: BOGPZYMHTVAROG-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhex-5-en-1-ol 、 (S)-3-(tert-butyldimethylsilyloxy)-1-cyclohexylpropan-1-ol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以62%的产率得到[(1S)-3-[tert-butyl(dimethyl)silyl]oxy-1-cyclohexylpropyl] (3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-methylhex-5-enoate
  参考文献：
  名称：

  Symmetric Macrocycles by a Prins Dimerization and Macrocyclization Strategy

  摘要：

  A tandem dimerization/macrocyclization reaction utilizing the Prins cyclization has been developed. This reaction develops molecular complexity through the formation of highly substituted dimeric tetrahydropyran macrocycles. Mild conditions utilizing rhenium(VII) catalysts were explored for aromatic substrates, while harsher Lewis acidic conditions were used for aliphatic substrates. Both aldehydes and acetals are shown to be viable substrates for this reaction.

  DOI：

  10.1021/ol9022062
• 作为产物：
  描述：

  (3S)-3-[(tert-butyldimethylsilyl)oxy]-4-methyl-5-hexen-1-ol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 以66%的产率得到(3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhex-5-en-1-ol
  参考文献：
  名称：

  Symmetric Macrocycles by a Prins Dimerization and Macrocyclization Strategy

  摘要：

  A tandem dimerization/macrocyclization reaction utilizing the Prins cyclization has been developed. This reaction develops molecular complexity through the formation of highly substituted dimeric tetrahydropyran macrocycles. Mild conditions utilizing rhenium(VII) catalysts were explored for aromatic substrates, while harsher Lewis acidic conditions were used for aliphatic substrates. Both aldehydes and acetals are shown to be viable substrates for this reaction.

  DOI：

  10.1021/ol9022062

文献信息

• Symmetric Macrocycles by a Prins Dimerization and Macrocyclization Strategy
  作者：Michael R. Gesinski、Kwanruthai Tadpetch、Scott D. Rychnovsky

  DOI：10.1021/ol9022062

  日期：2009.11.19

  A tandem dimerization/macrocyclization reaction utilizing the Prins cyclization has been developed. This reaction develops molecular complexity through the formation of highly substituted dimeric tetrahydropyran macrocycles. Mild conditions utilizing rhenium(VII) catalysts were explored for aromatic substrates, while harsher Lewis acidic conditions were used for aliphatic substrates. Both aldehydes and acetals are shown to be viable substrates for this reaction.