1-phenylpropyl hydroperoxide | 190506-77-5

• 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-phenylpropyl hydroperoxide
• 英文别名: (R)-1-phenyl-propyl hydroperoxide；(R)-1-Phenyl-propylhydroperoxid；[(1R)-1-hydroperoxypropyl]benzene
• CAS: 190506-77-5
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: JYLUDNGUBXOJPX-SECBINFHSA-N

物化性质

• 沸点：
  265.0±19.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三苯基甲醇 、 1-phenylpropyl hydroperoxide 在 硫酸 、 溶剂黄146 作用下， 生成 (+-)-(1-phenyl-propyl)-trityl peroxide
  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
• 作为产物：
  描述：

  S(-)-1-苯基-1-丙醇 在 硫酸 、 双氧水 作用下， 生成 1-phenylpropyl 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

• Kinetic Resolution of Hydroperoxides with Enantiopure Phosphines:  Preparation of Enantioenriched Tertiary Hydroperoxides
  作者：Tom G. Driver、Jason R. Harris、K. A. Woerpel

  DOI：10.1021/ja070482f

  日期：2007.4.1

  kinetic resolution strategy capable of accessing optically active tertiary hydroperoxides is reported. Readily accessible tertiary hydroperoxides are resolved with commercially available (R)- or (S)-xylyl-PHANEPHOS with selectivity factors as large as 37. The resulting bis(phosphine oxide) can be recycled in high yields. The isolated mono(phosphine oxide) intermediate resolved hydroperoxides with the

  报告了一种能够访问光学活性叔氢过氧化物的有效还原动力学拆分策略。容易获得的叔氢过氧化物用市售的 (R)- 或 (S)-二甲苯基-PHANEPHOS 拆分，选择性因子高达 37。得到的双（氧化膦）可以高产率回收。分离的单（氧化膦）中间体以与母体双膦相同的选择性拆分氢过氧化物。
• Asymmetric Synthesis with the Enzyme <i>Coprinus</i> Peroxidase:  Kinetic Resolution of Chiral Hydroperoxides and Enantioselective Sulfoxidation
  作者：Waldemar Adam、Cordula Mock-Knoblauch、Chantu R. Saha-Möller

  DOI：10.1021/jo990201p

  日期：1999.6.1

  hydroperoxide 1a afforded with CiP enantiomerically enriched hydroperoxide 1a (ee up to 54%) and alcohol 2a (ee up to 40%), as well as ketone 3a (which is also formed simultaneously in all other reactions) and molecular oxygen. Catalase activity was established for CiP with hydrogen peroxide. When aryl alkyl sulfides 4 were used as oxygen acceptors, three products, sulfoxides 5, alcohols 2, and hydroperoxides

  Coprinus过氧化物酶（CiP）用于外消旋氢过氧化物1的动力学拆分和前手性硫化物4的不对称硫氧化。在动力学分辨率的条件下，CiP和愈创木酚作为还原剂还原了11种氢过氧化物1a-k，对映选择性最高> （S）-氢过氧化物1的98％和（R）-醇2的90％。在没有还原剂的情况下，氢过氧化物1a提供了CiP对映异构体富集的氢过氧化物1a（ee最高为54％）和醇2a（ ee高达40％），酮3a（在所有其他反应中也同时形成）和分子氧。用过氧化氢确定了CiP的过氧化氢酶活性。将芳基烷基硫化物4用作氧受体时，得到三种产物：亚砜5，醇2和氢过氧化物1，全部以对映体富集的形式存在。衍生自萘基甲基硫化物（4f）的亚砜的最高ee值（89％）。因此，CiP可用于光学活性氢过氧化物1，醇2和亚砜5的不对称合成。
• Kinetic Resolution of Chiral Hydroperoxides:  Hydrogen-Peroxide-Mediated Screening of Peroxidase-Active Soil Bacteria
  作者：Waldemar Adam、Barbara Boss、Dag Harmsen、Zoltan Lukacs、Chantu R. Saha-Möller、Peter Schreier

  DOI：10.1021/jo9818327

  日期：1998.10.1
• 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：2024.5.21

  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.