3-[8(Z),11(Z)-pentadecadienyl] phenol | 51546-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-[8(Z),11(Z)-pentadecadienyl] phenol
• 英文别名: [3-(8Z)-8-pentadecen-1-ylphenol]；cardanol diene；cardanol monoene；3-(pentadecadien-(8c,11c)-yl)-phenol；3-[(8Z,11Z)-8,11-pentadecadienyl]phenol；3-[(8Z,11Z)-pentadeca-8,11-dienyl]phenol
• CAS: 51546-63-5
• 化学式: C₂₁H₃₂O
• 分子量: 300.484
• InChiKey: FAYVLNWNMNHXGA-UTOQUPLUSA-N

物化性质

• 沸点：
  434.9±24.0 °C(Predicted)
• 密度：
  0.931±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：20mg/mL； DMSO：15mg/mL；乙醇：22mg/mL；乙醇:PBS(pH 7.2) (1:1): 0.5 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-[8(Z),11(Z)-pentadecadienyl] phenol 在 镍 氢气 作用下， 生成 3-十五烷基苯酚
  参考文献：
  名称：

  Sethi,S.C.; Rao,B.C.S., Indian Journal of Chemistry, 1964, vol. 2, p. 277 - 282

  摘要：

  DOI：
• 作为产物：
  描述：

  6-氯-1-己醇 在 palladium on activated charcoal 、 palladium on barium sulfate 喹啉 、 盐酸 、 lithium amide 、 硫酸 、 乙基溴化镁 、 氢气 、 三溴化硼 、 三溴化磷 、 lithium 、 对甲苯磺酸 、 ferric nitrate 、 copper(l) chloride 、 三氯氧磷 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 、 乙酸乙酯 为溶剂， 反应 214.0h， 生成 3-[8(Z),11(Z)-pentadecadienyl] phenol
  参考文献：
  名称：

  Caplin, Joseph; Tyman, John H. P., Journal of Chemical Research, Miniprint, 1982, # 2, p. 321 - 351

  摘要：

  DOI：

文献信息

• Photoageing of cardanol: characterization, circumvention by side chain methoxylation and application for photocrosslinkable polymers
  作者：T. Fouquet、L. Fetzer、G. Mertz、L. Puchot、P. Verge

  DOI：10.1039/c5ra02858b

  日期：——

  Photoageing of cardanol and its limitation by methoxylation of the side chain to produce photocrosslinkable copolymers of tunable reactivity.

  卡豆醇的光老化及其通过甲氧基化侧链来限制的方法，以生产可调节反应性的光交联共聚物。
• Modulating nanostructure morphology and mesomorphic properties using unsaturation in cardanol – azo benzenes
  作者：Anjali Raju、Jyothish Kuthanapillil、Manoj Mathews、Shankar D. Rao、Jijo J. Vallooran、George John

  DOI：10.1039/d2cc06766h

  日期：——

  Herein, we report the synthesis and self-assembly of a new class of amphiphilic azo dyes derived from a plant-based phenol, cardanol. Analysis of the self-assembly of these new azo derivatives was intriguing, and they exhibit some unique nanostructures, such as bicelles and microgel-like structures, and smectic-type thermotropic mesophases.

  在此，我们报告了一类新的两亲性偶氮染料的合成和自组装，该染料源自植物性苯酚腰果酚。对这些新型偶氮衍生物的自组装分析很有趣，它们表现出一些独特的纳米结构，例如双胞胎和微凝胶状结构，以及近晶型热致中间相。
• Valorization of Madagascar’s CNSL via the synthesis of one advanced intermediate (3-Pentadecylcyclohexanone)
  作者：Andrianarivo Irène Rahobinirina、Maonja Finaritra Rakotondramanga、Alexandra Berlioz-Barbier、Estelle Métay、Voahangy Ramanandraibe、Marc Lemaire

  DOI：10.1016/j.tetlet.2017.04.093

  日期：2017.6

  A unique advanced intermediate: 3-Pentadecylcyclohexanone was synthetized from the crude product which contained a mixture of cardanol, cardol and 2-methylcardol, which was hydrogenated onto Pd/C at 80 degrees C. From this alkylated cyclohexanone: C15 alkylated adipic acid, caprolactam, caprolactone, were synthetized in high yields, such products may have many potentially applications in polymer chemistry. The condensation of the 3-pentadecyl-cyclohexanone and triethylene glycol in oxidative or reductive conditions gave aryl ether and cyclohexyl ether, this may be a way to prepare intermediate for surfactant chemistry. Therefore we show that Cashew Nut Shell Liquid (CNSL) may lead to numerous useful compounds thank to the preparation of a unique advanced intermediate. (C) 2017 Elsevier Ltd. All rights reserved.
• Monofunctional benzoxazine from cardanol for bio-composite applications
  作者：B.S. Rao、Aruna Palanisamy

  DOI：10.1016/j.reactfunctpolym.2010.11.025

  日期：2011.2

  In this study, a monofunctional benzoxazine monomer was synthesized by condensation reaction of aniline and formaldehyde with cardanol, a by product of cashew nut shell liquid (CNSL). The monomer was characterized by FTIR and (1)H NMR spectral analysis. Curing characteristics were studied by differential scanning calorimeter. The exothermic peak associated with curing was observed from 230 degrees C to 291 degrees C with a peak maximum of 272 degrees C. Adding a small percentage of cardanol as phenolic initiator reduced the onset of cure as well as peak maximum temperature due to accelerated curing. Thermo gravimetric analysis indicated a peak decomposition temperature of 432 degrees C and a char yield of 24% at 800 degrees C. The viscoelastic properties of the neat cardanol benzoxazine, its jute fiber composite and the acrylonitrile modified jute fiber composites were studied with dynamic mechanical thermal analyzer (DMTA). The storage modulus (E') value increased with fiber loading and showed a higher value for treated composite indicating an increase in interaction between fiber and resin matrix. On the other hand, the tan 6 which is associated with glass transition, shifted to lower value compared to neat resin with incorporation of jute fibers. (C) 2010 Elsevier Ltd. All rights reserved.
• Dioxygenation of Long-Chain Alkadien(trien)ylphenols by Soybean Lipoxygenase
  作者：Monika Roth、Birgit Gutsche、Markus Herderich、Hans-Ulrich Humpf、Peter Schreier

  DOI：10.1021/jf980196a

  日期：1998.8.17

  Long-chain alkadien(trien)ylphenols, i.e., cardanols, cardols, and anacardic acids, as well as their acetylated and methylated derivatives were used in enzymatic dioxygenation catalyzed by soybean lipoxygenase-1 (LOX-1). Kinetic studies revealed the influence of functional groups, chain length, number of double bonds, and the distance of the double bonds from the terminal end. Free functional groups were found to be a structural prerequisite for high affinity and turnover number; exceptional kinetic parameters were obtained for omega-6 compounds possessing the same chain length as linoleic acid. The regioselectivity and enantioselectivity of LOX-1 catalysis were investigated with 3-[(Z,Z)-8',11'-pentadecadienyl]phenol as the representative substrate, yielding 3-[12'-(S)-hydroperoxy-(Z,E)-8',10'-pentadecadienyl]phenol as the main product, Our extensive chromatographic and spectroscopic studies comprised HPLC-MS/MS for differentiation of the regioisomers, H-1 NMR spectroscopy for determination of the double-bond configuration, GC-MS to evaluate the enantiomeric excess, and exciton-coupled circular dichroism for determination of the absolute configuration.