6-hydroperoxy-3,7-dimethyl octa-1,7-dien-3-ol | 51276-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-hydroperoxy-3,7-dimethyl octa-1,7-dien-3-ol
• 英文别名: 1,7-Octadien-3-ol, 6-hydroperoxy-3,7-dimethyl-；6-hydroperoxy-3,7-dimethylocta-1,7-dien-3-ol
• CAS: 51276-31-4
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: XTQBSJUTCSCXME-UHFFFAOYSA-N

物化性质

• 沸点：
  314.1±42.0 °C(Predicted)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  6
• 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：

  芳樟醇 在 ethylene glycol-modified [Mg,Al(OH)_x][(MoO₄^(2-))(NO₃(-))] 双氧水 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (5E)-7-hydroperoxy-3,7-dimethylocta-1,5-dien-3-ol 、 6-hydroperoxy-3,7-dimethyl octa-1,7-dien-3-ol
  参考文献：
  名称：

  乙二醇改性的钼酸盐催化剂，可有效地由过氧化氢产生单线态氧。

  摘要：

  与多元醇相比，在多元醇（如乙二醇）中进行钼酸盐交换的层状双氢氧化物的预处理可得到均相催化剂，其氧化效率大大提高。

  DOI：

  10.1039/b704238h

文献信息

• Lanthanum-exchanged zeolites as active and selective catalysts for the generation of singlet oxygen from hydrogen peroxide
  作者：Joos Wahlen、Dirk De Vos、Sigrid De Hertogh、V�ronique Nardello、Jean-Marie Aubry、Paul Alsters、Pierre Jacobs

  DOI：10.1039/b414597f

  日期：——

  Lanthanum(III)-exchanged zeolites Beta and USY are active and selective catalysts for the generation of singlet oxygen from H2O2 showing superior activity and oxidant efficiency compared to unsupported La-catalysts, e.g. La(OH)3.

  镧（III）交换的沸石Beta和USY是从H2O2产生单线态氧的活性和选择性催化剂，与未负载的La催化剂（例如La（OH）3）相比，其活性和氧化剂效率更高。
• Porphyrin-Functionalized Dendrimers: Synthesis and Application as Recyclable Photocatalysts in a Nanofiltration Membrane Reactor
  作者：Suhas A. Chavan、Wouter Maes、Lieven E. M. Gevers、Joos Wahlen、Ivo F. J. Vankelecom、Pierre A. Jacobs、Wim Dehaen、Dirk E. De Vos

  DOI：10.1002/chem.200500251

  日期：2005.11.4

  porphyrin catalysts. Recycling of the dendrimer-enlarged homogeneous photocatalysts was possible by solvent-resistant nanofiltration (SRNF) by using an oxidatively stable membrane consisting of a polysiloxane polymer and ultrastable Y zeolite as inorganic filler. Moreover, this membrane technology provides a safe way to isolate the hydroperoxide products under very mild conditions. The membrane showed high

  一系列卟啉官能化的嘧啶树状大分子的聚合合成已经通过涉及亲核芳族取代（NAS）作为关键反应步骤的方法完成。所得的树枝状卟啉催化剂在光诱导的基态氧单线态氧（（1）O2）的产生中显示出高活性。这些材料是合成有用的光敏剂，用于将各种烯烃化合物氧化为相应的烯丙基氢过氧化物。树状光敏剂的催化活性，区域选择性和立体选择性与单核卟啉催化剂所观察到的相当。通过使用由聚硅氧烷聚合物和超稳定Y沸石组成的氧化稳定膜作为无机填料，可通过耐溶剂纳米过滤（SRNF）来回收树枝状大分子均相光催化剂。而且，这种膜技术提供了一种在非常温和的条件下分离氢过氧化物产物的安全方法。该膜即使在氯化溶剂中也显示出对大分子催化剂的高保留率，但是在多次催化运行中观察到了树枝状大分子的卟啉单元的某些氧化降解。
• Efficient Solar Photooxygenation with Supported Porphyrins as Catalysts
  作者：Sónia Ribeiro、Arménio C. Serra、António M. d' A. Rocha Gonsalves

  DOI：10.1002/cctc.201200532

  日期：2013.1

  Sunny side up: A very simple and efficient singlet‐oxygen‐mediated oxidative system that uses solar radiation, molecular oxygen, and Merrifield‐supported porphyrins is presented.

  阳光明媚的一面：提出了一个非常简单有效的单线态氧介导的氧化系统，该系统使用太阳辐射，分子氧和Merrifield支撑的卟啉。
• Selective C–H Allylic Oxygenation of Cycloalkenes and Terpenoids Photosensitized by [Cu(Xantphos)(neoc)]BF₄
  作者：Michael G. Kallitsakis、Dimitra K. Gioftsidou、Marina A. Tzani、Panagiotis A. Angaridis、Michael A. Terzidis、Ioannis N. Lykakis

  DOI：10.1021/acs.joc.1c01591

  日期：2021.10.1

  We present herein for the first time the use of the [Cu(Xantphos)(neoc)]BF4 as a photocatalyst for the selective C–H allylic oxygenation of cycloalkenes into the corresponding allylic hydroperoxides or alcohols in the presence of molecular oxygen. The proposed methodology affords the products at good yields and has also been applied successfully to several bioactive terpenoids, such as geraniol, linalool

  我们在此首次提出使用 [Cu(Xantphos)(neoc)]BF 4作为光催化剂，在分子氧存在下将环烯烃选择性 C-H 烯丙基氧化成相应的烯丙基氢过氧化物或醇。所提出的方法以良好的产量提供了产品，并且还成功地应用于几种生物活性萜类化合物，如香叶醇、芳樟醇、β-香茅醇和植醇。一项还涉及动力学同位素效应 (KIE) 的机械研究支持所提出的单线态氧介导的反应。基于观察到的高化学选择性和产率以及快速和清洁的反应过程，本催化体系 [Cu(Xantphos)(neoc)]BF 4也已应用于实验室规模的合成顺式玫瑰氧化物，一种众所周知的香料成分，用于玫瑰和天竺葵香水。
• 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.