3-<(Methoxymethoxy)methyl>-4-penten-3-ol | 170450-93-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-<(Methoxymethoxy)methyl>-4-penten-3-ol
• 英文别名: 3-(Methoxymethoxymethyl)pent-1-en-3-ol
• CAS: 170450-93-8
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: VBCBIJLILNEMCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-<(Methoxymethoxy)methyl>-4-penten-3-ol 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-Methyl-5-<(methoxymethoxy)methyl>-4(Z)-heptenoic acid
  参考文献：
  名称：

  A Chelation-Controlled Ester Enolate Claisen Rearrangement

  摘要：

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state. An oxygen-bearing functional group at the tertiary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. alpha,beta-Disubstituted unsaturated carboxylic acids are also formed with high diastereoselectivity.

  DOI：

  10.1021/jo00121a029
• 作为产物：
  描述：

  乙烯基溴化镁 、 1-(Methoxymethoxy)-2-butanone 以 乙醚 为溶剂， 反应 1.0h， 以60%的产率得到3-<(Methoxymethoxy)methyl>-4-penten-3-ol
  参考文献：
  名称：

  A Chelation-Controlled Ester Enolate Claisen Rearrangement

  摘要：

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state. An oxygen-bearing functional group at the tertiary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. alpha,beta-Disubstituted unsaturated carboxylic acids are also formed with high diastereoselectivity.

  DOI：

  10.1021/jo00121a029

文献信息

• A ligand assisted Claisen rearrangement
  作者：Marie E. Krafft、Sandra Jarrett、Olivier A. Dasse

  DOI：10.1016/s0040-4039(00)61392-8

  日期：1993.12

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes via heteroatom mediated substrate pre-organization prior to rearrangement.
• A Chelation-Controlled Ester Enolate Claisen Rearrangement
  作者：Marie E. Krafft、Olivier A. Dasse、Sandra Jarrett、Anne Fievre

  DOI：10.1021/jo00121a029

  日期：1995.8

  The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state. An oxygen-bearing functional group at the tertiary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. alpha,beta-Disubstituted unsaturated carboxylic acids are also formed with high diastereoselectivity.