1-(5-(hydroxy-d)cyclopent-1-en-1-yl)octan-1-one | 1361293-36-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(5-(hydroxy-d)cyclopent-1-en-1-yl)octan-1-one
• CAS: 1361293-36-8
• 化学式: C₁₃H₂₂O₂
• 分子量: 211.309
• InChiKey: KYKOJVCZRIBQKA-RWFJLFJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  15.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-heptyl-3,4-dioxabicyclo[3.3.0]oct-1(8)-ene-2-d 在 氧气 作用下， 以 乙腈 为溶剂， 反应 2.5h， 以5.2%的产率得到1-(5-(hydroxy-d)cyclopent-1-en-1-yl)octan-1-one
  参考文献：
  名称：

  Unveiling the Role of Molecule-Assisted Homolysis: A Mechanistic Probe into the Chemistry of a Bicyclic Peroxide

  摘要：

  Unlike the reaction of aryl-substituted diazenes, pyrolysis of alkyl-substituted diazenes in the presence of molecular oxygen generates an unexpectedly complex product mixture. Using deuterium labeling studies, in conjunction with quantum calculations, a reasonable mechanistic hypothesis for the decomposition of the resultant [3.3.0] peroxide, and subsequent formation of the keto-alcohol and Z-configured alpha,beta-unsaturated keto-aldehyde, is proposed. Surprisingly, molecule-assisted homolysis plays a key role in this transformation, the details of which are discussed herein.

  DOI：

  10.1021/jo300297u