1-phenylbutyl hydroperoxide | 58687-89-1

• 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: 1-phenylbutyl hydroperoxide
• 英文别名: (R)-1-phenyl-butyl hydroperoxide；(R)-1-Phenyl-butylhydroperoxid；[(1R)-1-hydroperoxybutyl]benzene
• CAS: 58687-89-1
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: GCTYTOVBYDPZIX-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (R)-(+)-1-苯基-1-丁醇 在 硫酸 、 双氧水 作用下， 生成 1-phenylbutyl hydroperoxide
  参考文献：
  名称：

  934.有机过氧化物。第九部分 由过氧化氢形成烷基氢过氧化物的立体化学研究

  摘要：

  DOI：

  10.1039/jr9580004637

文献信息

• Peroxygenase‐Enabled Reductive Kinetic Resolution for the Enantioenrichment of Organoperoxides
  作者：Qianqian Shen、Juzhang Yan、Yuchen Han、Zaoxiao Zhang、Huanhuan Li、Dulin Kong、Jianjun Shi、Chengsen Cui、Wuyuan Zhang

  DOI：10.1002/anie.202401590

  日期：——

  Enantiomerically pure organoperoxides serve as valuable precursors in organic transformations. Herein, we present the first examples of unspecific peroxygenase catalyzed kinetic resolution of racemic organoperoxides through asymmetric reduction. Through meticulous investigation of the reaction conditions, it is shown that the unspecific peroxygenase from Agrocybe aegerita (AaeUPO) exhibits robust catalytic activity in the kinetic resolution reactions of the model substrate with turnover numbers up to 60000 and turnover frequency of 5.6 s⁻¹. Various aralkyl organoperoxides were successfully resolved by AaeUPO, achieving excellent enantioselectivities (e.g., up to 99 % ee for the (S)‐organoperoxide products). Additionally, we screened commercial peroxygenase variants to obtain the organoperoxides with complementary chirality, with one mutant yielding the (R)‐products. While unspecific peroxygenases have been extensively demonstrated as a powerful oxidative catalysts, this study highlights their usefulness in catalyzing the reduction of organoperoxides and providing versatile chiral synthons.
• 934. Organic peroxides. Part IX. A stereochemical study of the formation of alkyl hydroperoxides from hydrogen peroxide
  作者：Alwyn G. Davies、R. Feld

  DOI：10.1039/jr9580004637

  日期：——