(2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dien-1-ol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dien-1-ol
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: UYFVWWJTLUHGLJ-KRHXFINASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  香叶醇 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 11.25h， 生成 (2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dien-1-ol 、 (E)-6-Hydroperoxy-3,7-dimethyl-octa-2,7-dien-1-ol
  参考文献：
  名称：

  Kinetics of the Oxygenation of Unsaturated Organics with Singlet Oxygen Generated from H₂O₂ by a Heterogeneous Molybdenum Catalyst

  摘要：

  A heterogeneous catalyst containing MoO42- exchanged on layered double hydroxides (Mo-LDHs) is used to produce O-1(2) from H2O2, and with this dark O-1(2), unsaturated hydrocarbons are oxidized in allylic peroxides. The oxidation kinetics are studied in detail and are compared with the kinetics of oxidation by O-1(2), formed from H2O2 by a homogeneous catalyst. A model is proposed for the heterogeneously catalyzed O-1(2) generation and peroxide formation. The model divides the reaction suspension in two compartments: (1) the intralamellar and intragranular zones of the LDH catalyst; (2) the bulk solution. The 2-compartment model correctly predicts the oxidant efficiency and peroxide yield for a series of olefin peroxidation reactions. O-1(2) is generated at a high rate by the heterogeneous catalyst, but somewhat more O-1(2) is lost by quenching with the heterogeneous catalyst than using the homogeneous catalyst. Quenching occurs mainly as a result of collision with the LDH hydroxyl surface, as is evidenced by using LDH supports containing strong O-1(2) deactivators such as Ni2+. A total of 15 organic substrates were peroxidized on a preparative scale using the best Mo-LDH catalyst under optimal conditions.

  DOI：

  10.1021/ja065849f

文献信息

• Isoprenoid Alcohols are Susceptible to Oxidation with Singlet Oxygen and Hydroxyl Radicals
  作者：Joanna Komaszylo née Siedlecka、Magdalena Kania、Marek Masnyk、Piotr Cmoch、Iwona Lozinska、Zbigniew Czarnocki、Karolina Skorupinska-Tudek、Witold Danikiewicz、Ewa Swiezewska

  DOI：10.1007/s11745-015-4104-y

  日期：2016.2

  characterized. In this study, chemical oxidation of isoprenoid alcohols (Prenol-2 and -10) was performed using singlet oxygen (generated in the presence of hydrogen peroxide/molybdate or upon photochemical reaction in the presence of porphyrin), oxygen (formed upon hydrogen peroxide dismutation) or hydroxyl radical (generated by the hydrogen peroxide/sonication, UV/titanium dioxide or UV/hydrogen peroxide) systems

  作为所有活细胞共同成分的类异戊二烯暴露于氧化剂反应性氧，例如单线态氧或羟基自由基。尽管有这个事实，但从未对聚异戊二烯的氧化产物进行过表征。在这项研究中，使用单线态氧（在过氧化氢/钼酸盐存在下或在卟啉存在下进行光化学反应生成），氧（在过氧化氢歧化后形成）对类异戊二烯醇（Prenol-2和-10）进行化学氧化）或羟基自由基（由过氧化氢/超声处理，UV /二氧化钛或UV /过氧化氢生成）系统。借助质谱（MS）和核磁共振（NMR）方法研究了所得产物羟基，过氧和杂环衍生物的结构。此外，带有电喷雾电离的质谱似乎是检测类异戊二烯氧化产物（ESI-MS分析）以及根据选定离子的碎裂谱建立其结构的有用分析工具（ESI-MS / MS分析）。两者合计，首次显示了聚异戊二烯醇对各种氧化剂的敏感性。
• Photo-Oxygenation of geraniol: synthesis of a novel series of hydroxy-functionalized anti-malarial 1,2,4-trioxanes
  作者：Chandan Singh、Nitin Gupta、Sunil K Puri

  DOI：10.1016/s0960-894x(02)00320-7

  日期：2002.8

  Photo-oxygenation of geraniol 2, an abundantly available allylic alcohol, furnished a mixture of mono- and di-hydroperoxy products;the latter have been used for the preparation of a novel series of hydroxy-functionalized anti-malarial 1,2,4-trioxanes (7a-d, 8a-d). (C) 2002 Elsevier Science Ltd. All rights reserved.
• Process for Oxidizing Organic Substrates By Means of Singlet Oxygen Using a Modified Molybdate LDH Catalyst
  申请人：De Vos Dirk

  公开号：US20110098488A1

  公开（公告）日：2011-04-28

  Oxidation of organic substrates by means of singlet oxygen, in which organic substrates which react with 1 O 2 are admixed with 10-70% H 2 O 2 in an organic solvent in the presence of a molybdate LDH catalyst modified by ethylene glycol, polyethylene glycol or polyol, and the catalytic decomposition of H 2 O 2 to water and 1 O 2 is then followed by the oxidation to the corresponding oxidation products, and also modified molybdate LDH catalysts.
• Kinetics of the Oxygenation of Unsaturated Organics with Singlet Oxygen Generated from H₂O₂ by a Heterogeneous Molybdenum Catalyst
  作者：Bert F. Sels、Dirk E. De Vos、Pierre A. Jacobs

  DOI：10.1021/ja065849f

  日期：2007.5.1

  A heterogeneous catalyst containing MoO42- exchanged on layered double hydroxides (Mo-LDHs) is used to produce O-1(2) from H2O2, and with this dark O-1(2), unsaturated hydrocarbons are oxidized in allylic peroxides. The oxidation kinetics are studied in detail and are compared with the kinetics of oxidation by O-1(2), formed from H2O2 by a homogeneous catalyst. A model is proposed for the heterogeneously catalyzed O-1(2) generation and peroxide formation. The model divides the reaction suspension in two compartments: (1) the intralamellar and intragranular zones of the LDH catalyst; (2) the bulk solution. The 2-compartment model correctly predicts the oxidant efficiency and peroxide yield for a series of olefin peroxidation reactions. O-1(2) is generated at a high rate by the heterogeneous catalyst, but somewhat more O-1(2) is lost by quenching with the heterogeneous catalyst than using the homogeneous catalyst. Quenching occurs mainly as a result of collision with the LDH hydroxyl surface, as is evidenced by using LDH supports containing strong O-1(2) deactivators such as Ni2+. A total of 15 organic substrates were peroxidized on a preparative scale using the best Mo-LDH catalyst under optimal conditions.