3-<(Methoxymethoxy)methyl>-cis-4-hexenyl 3-propionate | 170450-86-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-<(Methoxymethoxy)methyl>-cis-4-hexenyl 3-propionate
• 英文别名: [(E)-3-(methoxymethoxymethyl)hex-4-en-3-yl] propanoate
• CAS: 170450-86-9
• 化学式: C₁₂H₂₂O₄
• 分子量: 230.304
• InChiKey: RWVCJQWMEJPBKY-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-<(Methoxymethoxy)methyl>-cis-4-hexenyl 3-propionate 在 bromomagnesium diethylamide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 为溶剂， 生成 anti-2,3-Dimethyl-5-<(methoxymethoxy)methyl>-4(Z)-heptenoic acid 、 anti-2,3-Dimethyl-5-<(methoxymethoxy)methyl>-4(E)-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：

  1-(Methoxymethoxy)-2-butanone 在 lithium aluminium tetrahydride 、 乙基溴化镁 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 9.33h， 生成 3-<(Methoxymethoxy)methyl>-cis-4-hexenyl 3-propionate
  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 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.