(2S,3S)-3-Vinyl-butane-1,2,4-triol | 276879-09-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3S)-3-Vinyl-butane-1,2,4-triol
• 英文别名: (2S,3S)-3-ethenylbutane-1,2,4-triol
• CAS: 276879-09-5
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: BZEBVQHOMVJJTK-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-Vinyl-butane-1,2,4-triol 在 4-甲基苯磺酸吡啶 咪唑 、 原乙酸三甲酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-dimethyl-silanyloxymethyl)-hex-5-enenitrile
  参考文献：
  名称：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2-cyclohexenone as a useful chiral building block for preparation of substituted cyclohexane rings: synthesis and its highly stereoselective reaction with RCu(CN)Li

  摘要：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2cyclohexenone (2) has been synthesized in 25% overall yield starting from easily available 1,4-bis(benzyloxy)-2,3-epoxy butane (3). The enone 2 reacts with excellent stereoselectivity with RCu(CN)Li thus working as an efficient chiral building block for preparation of substituted cyclohexane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00239-2
• 作为产物：
  描述：

  (2S,3S)-1-Benzyloxy-3-benzyloxymethyl-pent-4-en-2-ol 在 氨 、 lithium 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到(2S,3S)-3-Vinyl-butane-1,2,4-triol
  参考文献：
  名称：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2-cyclohexenone as a useful chiral building block for preparation of substituted cyclohexane rings: synthesis and its highly stereoselective reaction with RCu(CN)Li

  摘要：

  Optically active trans-4-(tert-butyldimethylsiloxymethyl)-5-(tert-butyldimethylsiloxy)-2cyclohexenone (2) has been synthesized in 25% overall yield starting from easily available 1,4-bis(benzyloxy)-2,3-epoxy butane (3). The enone 2 reacts with excellent stereoselectivity with RCu(CN)Li thus working as an efficient chiral building block for preparation of substituted cyclohexane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00239-2