(Z)-4-(2-bromo-1-ethoxyethoxy)-2-buten-1-ol

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-4-(2-bromo-1-ethoxyethoxy)-2-buten-1-ol
• 英文别名: (Z)-4-(2-bromo-1-ethoxyethoxy)but-2-en-1-ol
• 化学式: C₈H₁₅BrO₃
• 分子量: 239.109
• InChiKey: OARVDLKWQXLVMV-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12
• 可旋转键数：
  7
• 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：

  (Z)-4-(2-bromo-1-ethoxyethoxy)-2-buten-1-ol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 2-((3S,5R)-5-Ethoxy-tetrahydro-furan-3-yl)-ethanol 、 2-((3R,5R)-5-Ethoxy-tetrahydro-furan-3-yl)-ethanol
  参考文献：
  名称：

  Formation of Some Oxygen-Containing Heterocycles by Radical Cyclization:  The Stereochemical Influence of Anomeric Effects

  摘要：

  The influence of the anomeric effect on radical cyclization has been examined by determining the stereochemical outcome of the ring closure of 10 suitably substituted radicals. The stereochemistry of the products formed from the acyclic precursors 4a-f indicates that for suitably constituted radicals anomeric interactions stabilize pseudoaxially substituted transition structures 14 thus affording products with stereochemistry the reverse of that normally observed.

  DOI：

  10.1021/jo980359u
• 作为产物：
  描述：

  顺式-1,2-二羟甲基乙烯 、 乙烯基乙醚 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以69%的产率得到(Z)-4-(2-bromo-1-ethoxyethoxy)-2-buten-1-ol
  参考文献：
  名称：

  Formation of Some Oxygen-Containing Heterocycles by Radical Cyclization:  The Stereochemical Influence of Anomeric Effects

  摘要：

  The influence of the anomeric effect on radical cyclization has been examined by determining the stereochemical outcome of the ring closure of 10 suitably substituted radicals. The stereochemistry of the products formed from the acyclic precursors 4a-f indicates that for suitably constituted radicals anomeric interactions stabilize pseudoaxially substituted transition structures 14 thus affording products with stereochemistry the reverse of that normally observed.

  DOI：

  10.1021/jo980359u

文献信息

• Formation of Some Oxygen-Containing Heterocycles by Radical Cyclization:  The Stereochemical Influence of Anomeric Effects
  作者：Athelstan L. J. Beckwith、Dennis M. Page

  DOI：10.1021/jo980359u

  日期：1998.7.1

  The influence of the anomeric effect on radical cyclization has been examined by determining the stereochemical outcome of the ring closure of 10 suitably substituted radicals. The stereochemistry of the products formed from the acyclic precursors 4a-f indicates that for suitably constituted radicals anomeric interactions stabilize pseudoaxially substituted transition structures 14 thus affording products with stereochemistry the reverse of that normally observed.