3-phenylselenylcyclobutene | 847158-87-6

• 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: 3-phenylselenylcyclobutene
• 英文别名: (2-Cyclobuten-1-ylseleno)-benzene；cyclobut-2-en-1-ylselanylbenzene
• CAS: 847158-87-6
• 化学式: C₁₀H₁₀Se
• 分子量: 209.149
• InChiKey: JJXHKCIOOAOREV-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于二氯甲烷、乙醚、乙酸乙酯

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  3-phenylselenylcyclobutene 在 naphthalen-1-yl-lithium 、 硼酸三甲酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 Cyclobut-2-en-1-ylboronic acid
  参考文献：
  名称：

  Contrasteric Stereochemical Dictation of the Cyclobutene Ring-Opening Reaction by a Vacant Boron p Orbital

  摘要：

  Cyclobutene, having a pinacolatoboryl group at the 3-position, was prepared by the reaction of trimethyl borate with a cyclobutenyl anion, which was generated by reductive lithiation of 3-(phenylselenyl)cyclobutene. Its thermal ring-opening reaction provided (Z)-1-borylbuta-1,3-diene selectively despite the arising steric congestion. The contrasteric behavior was accounted for by assuming an electron-accepting interaction of the vacant boron p orbital with the distorted breaking sigma orbital in the inward transition state.

  DOI：

  10.1021/ja043979n
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以45%的产率得到3-phenylselenylcyclobutene
  参考文献：
  名称：

  Contrasteric Stereochemical Dictation of the Cyclobutene Ring-Opening Reaction by a Vacant Boron p Orbital

  摘要：

  Cyclobutene, having a pinacolatoboryl group at the 3-position, was prepared by the reaction of trimethyl borate with a cyclobutenyl anion, which was generated by reductive lithiation of 3-(phenylselenyl)cyclobutene. Its thermal ring-opening reaction provided (Z)-1-borylbuta-1,3-diene selectively despite the arising steric congestion. The contrasteric behavior was accounted for by assuming an electron-accepting interaction of the vacant boron p orbital with the distorted breaking sigma orbital in the inward transition state.

  DOI：

  10.1021/ja043979n