4-(biphenyl-4-yl)-3-hydroperoxypent-4-en-1-ol | 917100-91-5

• 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: 4-(biphenyl-4-yl)-3-hydroperoxypent-4-en-1-ol
• 英文别名: 3-Hydroperoxy-4-(4-phenylphenyl)pent-4-en-1-ol
• CAS: 917100-91-5
• 化学式: C₁₇H₁₈O₃
• 分子量: 270.328
• InChiKey: TXGFRHOIRMRNBB-UHFFFAOYSA-N

物化性质

• 熔点：
  73-75 °C
• 沸点：
  507.1±50.0 °C(predicted)
• 密度：
  1.148±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(biphenyl-4-yl)-3-hydroperoxypent-4-en-1-ol 在 hydrazinium carbazate 、 双氧水 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 84.0h， 以63%的产率得到4-biphenyl-4-yl-3-hydroperoxypentan-1-ol
  参考文献：
  名称：

  Hydrazinium Carbazate-H2O2: An Ideal Combination for Diimide Reduction of Base-Sensitive Unsaturated Peroxides¹

  摘要：

  介绍了一种氢肼氨基甲酸酯（N2H3COON2H5）与H2O2结合用于基础敏感的不饱和1,2,4-三氧烷、1,2,4-三氧烷以及其前体β-和γ-羟基过氧化氢的双键还原的实用性。该方法优于传统的使用N2H4·H2O-H2O2的二氮还原和催化氢化。

  DOI：

  10.1055/s-0029-1218639
• 作为产物：
  描述：

  4-(biphenyl-4-yl)pent-3-en-1-ol 在 氧气 、 亚甲兰 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以62%的产率得到4-(biphenyl-4-yl)-3-hydroperoxypent-4-en-1-ol
  参考文献：
  名称：

  Synthesis of 1,2,4-Trioxepanes and 1,2,4-Trioxocanes via Photooxygenation of Homoallylic Alcohols¹

  摘要：

  Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield gamma-hydroxyhydroperoxides 5a-d in 57-72% yield. Acid-catalyzed reaction of 5a-d with acetone, cyclopentanone, and cyclohexanone furnished 1,2,4-trioxepanes 8a-d, 9a-d, and 10a-d in good yields. Homoallylic alcohol 12 also underwent a highly regioselective photooxygenation to yield delta-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield.

  DOI：

  10.1021/jo061414z

文献信息

• Orally active 1,2,4-trioxepanes: Synthesis and antimalarial activity of a series of 7-arylvinyl-1,2,4-trioxepanes against multidrug-resistant Plasmodium yoelii in Swiss mice☆
  作者：Chandan Singh、Shilpi Pandey、Malvika Sharma、Sunil K. Puri

  DOI：10.1016/j.bmc.2007.11.012

  日期：2008.2.15

  7-Arylvinyl-1,2,4-trioxepanes 7a-d, 8a-d, 9a-d, 10a-d, 11a-c, and 12a-c, prepared by photooxygenation of homoallylic alcohols 5a-d, were evaluated against multi-drug resistant Plasmodium yoelii nigeriensis in Swiss mice by oral and intramuscular routes. Trioxepane 11c, the most active compound of the series, showed more than 98% suppression of parsitaemia at 96 mg/kg by both oral and intramuscular routes. This is the first report on in vivo active 1,2,4-trioxepanes. (C) 2007 Elsevier Ltd. All rights reserved.
• New functionalized 1,2,4-trioxepanes: Synthesis and antimalarial activity against multi-drug resistant P. yoelii in mice
  作者：Chandan Singh、Shilpi Pandey、Ambuj K. Kushwaha、Sunil K. Puri

  DOI：10.1016/j.bmcl.2008.08.096

  日期：2008.10

  A series of new amino functionalized 1,2,4-trioxepanes8-16 and ester functionalized 1,2,4-trioxepanes 17-19 have been synthesized and evaluated against multi-drug resistant Plasmodium yoelii in Swiss mice. Amino functionalized trioxepanes 14, the most active compound of the series, showed 100% clearance of parasitaemia by oral route on day 4 and 75% protection to the treated mice beyond day 28. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of 1,2,4-Trioxepanes and 1,2,4-Trioxocanes via Photooxygenation of Homoallylic Alcohols¹
  作者：Chandan Singh、Shilpi Pandey、Gunjan Saxena、Nisha Srivastava、Malvika Sharma

  DOI：10.1021/jo061414z

  日期：2006.11.1

  Homoallylic alcohols 4a-d, easily accessible in two steps from cyclopropyl methyl ketone, underwent a highly regioselective reaction with singlet oxygen to yield gamma-hydroxyhydroperoxides 5a-d in 57-72% yield. Acid-catalyzed reaction of 5a-d with acetone, cyclopentanone, and cyclohexanone furnished 1,2,4-trioxepanes 8a-d, 9a-d, and 10a-d in good yields. Homoallylic alcohol 12 also underwent a highly regioselective photooxygenation to yield delta-hydroxyhydroperoxide 13 in 67% yield, which on reaction with acetone, cyclopentanone, and cyclohexanone, furnished 1,2,4-trioxocanes 16-18 in 41-55% yield.
• Hydrazinium Carbazate-H2O2: An Ideal Combination for Diimide Reduction of Base-Sensitive Unsaturated Peroxides¹
  作者：Chandan Singh、Ajit Singh、Niraj Naikade、Ved Verma、Mohammad Hassam、Nitin Gupta、Shilpi Pandey

  DOI：10.1055/s-0029-1218639

  日期：2010.3

  The utility of a hydrazinium carbazate (N2H3COON2H5) and H2O2 combination for the double bond reduction of base-sensitive unsaturated 1,2,4-trioxanes, 1,2,4-trioxepanes, and their precursors β- and γ-hydroxyhydroperoxides is presented. The method is superior to the conventional diimide reduction using N2H4˙H2O-H2O2 and catalytic hydrogenation.

  介绍了一种氢肼氨基甲酸酯（N2H3COON2H5）与H2O2结合用于基础敏感的不饱和1,2,4-三氧烷、1,2,4-三氧烷以及其前体β-和γ-羟基过氧化氢的双键还原的实用性。该方法优于传统的使用N2H4·H2O-H2O2的二氮还原和催化氢化。