(1S,4R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enyl 2,2,2-trimethylacetate | 1061330-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,4R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enyl 2,2,2-trimethylacetate
• 英文别名: (1S,4R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enyl pivalate；[(1S,4R)-4-[(4-methoxyphenyl)methoxy]cyclopent-2-en-1-yl] 2,2-dimethylpropanoate
• CAS: 1061330-03-7
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: AMAPXPUDFUOAEU-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (1S,4R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enyl 2,2,2-trimethylacetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (1S,4R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enol
  参考文献：
  名称：

  Improved Synthesis of the Epoxy Isoprostane Phospholipid PEIPC and its Reactivity with Amines

  摘要：

  An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E-2-sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles.

  DOI：

  10.1021/ol8014804
• 作为产物：
  描述：

  4-甲氧基溴苄 、 (1S,4R)-4-hydroxycyclopent-2-enyl 2,2,2-trimethylacetate 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以61%的产率得到(1S,4R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enyl 2,2,2-trimethylacetate
  参考文献：
  名称：

  Improved Synthesis of the Epoxy Isoprostane Phospholipid PEIPC and its Reactivity with Amines

  摘要：

  An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E-2-sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles.

  DOI：

  10.1021/ol8014804

文献信息

• Improved Synthesis of the Epoxy Isoprostane Phospholipid PEIPC and its Reactivity with Amines
  作者：Michael E. Jung、Judith A. Berliner、Lukasz Koroniak、B. Gabriel Gugiu、Andrew D. Watson

  DOI：10.1021/ol8014804

  日期：2008.10.2

  An improved synthesis of the naturally occurring hydroxy ketone 1-palmitoyl-2-(5,6)-epoxyisoprostane E-2-sn-glycero-3-phosphocholine (PEIPC) 1, a compound that plays a role in endothelial activation in atherosclerosis, has been carried out using a PMB ether as the key protecting group. Opening of an intermediate with pentylamine shows that the allylic epoxide is the position of attack by nucleophiles.