3,5-bis(p-vinylphenylmethyloxy)benzyl alcohol | 304014-53-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-bis(p-vinylphenylmethyloxy)benzyl alcohol
• 英文别名: 3,5-Di(4-vinylbenzyloxy)benzyl alcohol；SD；3,5-Di(4-vinylbenzyloxy)benzylalcohol；[3,5-bis[(4-ethenylphenyl)methoxy]phenyl]methanol
• CAS: 304014-53-7
• 化学式: C₂₅H₂₄O₃
• 分子量: 372.464
• InChiKey: DKPLEMOVRBBAKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  63-65 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  569.4±45.0 °C(Predicted)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-bis(p-vinylphenylmethyloxy)benzyl alcohol 在 18-冠醚-6 、 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 68.0h， 生成 3,5-Di[3,5-di(4-vinylbenzyloxy)benzyloxy]benzyl alcohol
  参考文献：
  名称：

  Immobilization of BINOL by Cross-Linking Copolymerization of Styryl Derivatives with Styrene, and Applications in Enantioselective Ti and Al Lewis Acid Mediated Additions of Et2Zn and Me3SiCN to Aldehydes and of Diphenyl Nitrone to Enol Ethers

  摘要：

  The chiral ligand 1,1'-bi-2-naphthol (BINOL) has been succesfully immobilized on polystyrene. Several dendritic and non-dendritic BINOL derivatives (3, and 13-17), bearing at least two polymerizable styryl groups, were prepared and fully characterized. Suspension copolymerization of the MOM- or TIPS-protected cross-linking BINOL ligands (MOM = methyloxymethyl, TIPS = triisopropylsilyl) with styrene, cleavage of the protecting-groups, and loading with a Lewis-acid afforded catalytically active polystyrene-supported BINOLates. The polymer-bound BINOLs p-3, and p-13-p-16 were tested in the Ti-BINOLate-mediated addition of Et2Zn to PhCHO. The enantioselectivities (up to 93%) and conversions obtained with the polymer-bound catalysts were in most cases identical (within experimental error) to those obtained with the unsubstituted 1,1'-bi-2-naphthol and with the non-polymerized BINOL cross-linkers under homogeneous conditions. Special focus was put on the reusability of the supported catalyst: the polymer-beads were used in up to 20 consecutive catalytic runs, with the best polymers showing no or only minor loss of selectivity. BINOL-polymers p-17, obtained by copolymerization of a 3,3'-distyryl-substituted BINOL 17a with styrene, were used in the BINOL AlMe-mediated cycloaddition of diphenyl nitrone with alkyl vinyl ethers. In all cases the exolendo selectivity (greater than or equal to 92:8) and the enantioselectivities with which the exo-cycloadducts were formed (greater than or equal to 95%) correspond to those observed in the homogeneous reactions. A dendritically cross-linked BINOL-polymer was also employed in the Ti-BINOLate-mediated cyanosilylation of pivalaldehyde. The enantiopurity of the cyanohydrine obtained in the first run was as high as in the homogeneous reaction (72%); surprisingly the catalytic performance of the supported catalyst increased steadily during the first catalytic cycles to reach 83%. Thus, cross-linking BINOLs can be succesfully incorporated into a polystyrene matrix (without racemization!) to give poly mer-bound BINOL ligands that give excellent performance over many catalytic cycles with catalytic activities comparable with those of soluble analogues.

  DOI：

  10.1002/1521-3765(20001016)6:20<3692::aid-chem3692>3.0.co;2-0
• 作为产物：
  描述：

  3,5-二羟基苯甲酸甲酯 在 lithium aluminium tetrahydride 、 18-冠醚-6 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 64.0h， 生成 3,5-bis(p-vinylphenylmethyloxy)benzyl alcohol
  参考文献：
  名称：

  Immobilization of BINOL by Cross-Linking Copolymerization of Styryl Derivatives with Styrene, and Applications in Enantioselective Ti and Al Lewis Acid Mediated Additions of Et2Zn and Me3SiCN to Aldehydes and of Diphenyl Nitrone to Enol Ethers

  摘要：

  The chiral ligand 1,1'-bi-2-naphthol (BINOL) has been succesfully immobilized on polystyrene. Several dendritic and non-dendritic BINOL derivatives (3, and 13-17), bearing at least two polymerizable styryl groups, were prepared and fully characterized. Suspension copolymerization of the MOM- or TIPS-protected cross-linking BINOL ligands (MOM = methyloxymethyl, TIPS = triisopropylsilyl) with styrene, cleavage of the protecting-groups, and loading with a Lewis-acid afforded catalytically active polystyrene-supported BINOLates. The polymer-bound BINOLs p-3, and p-13-p-16 were tested in the Ti-BINOLate-mediated addition of Et2Zn to PhCHO. The enantioselectivities (up to 93%) and conversions obtained with the polymer-bound catalysts were in most cases identical (within experimental error) to those obtained with the unsubstituted 1,1'-bi-2-naphthol and with the non-polymerized BINOL cross-linkers under homogeneous conditions. Special focus was put on the reusability of the supported catalyst: the polymer-beads were used in up to 20 consecutive catalytic runs, with the best polymers showing no or only minor loss of selectivity. BINOL-polymers p-17, obtained by copolymerization of a 3,3'-distyryl-substituted BINOL 17a with styrene, were used in the BINOL AlMe-mediated cycloaddition of diphenyl nitrone with alkyl vinyl ethers. In all cases the exolendo selectivity (greater than or equal to 92:8) and the enantioselectivities with which the exo-cycloadducts were formed (greater than or equal to 95%) correspond to those observed in the homogeneous reactions. A dendritically cross-linked BINOL-polymer was also employed in the Ti-BINOLate-mediated cyanosilylation of pivalaldehyde. The enantiopurity of the cyanohydrine obtained in the first run was as high as in the homogeneous reaction (72%); surprisingly the catalytic performance of the supported catalyst increased steadily during the first catalytic cycles to reach 83%. Thus, cross-linking BINOLs can be succesfully incorporated into a polystyrene matrix (without racemization!) to give poly mer-bound BINOL ligands that give excellent performance over many catalytic cycles with catalytic activities comparable with those of soluble analogues.

  DOI：

  10.1002/1521-3765(20001016)6:20<3692::aid-chem3692>3.0.co;2-0

文献信息

• Highly Efficient and Stable Inverted Polymer Solar Cells Integrated with a Cross-Linked Fullerene Material as an Interlayer
  作者：Chao-Hsiang Hsieh、Yen-Ju Cheng、Pei-Jung Li、Chiu-Hsiang Chen、Martin Dubosc、Ru-Meng Liang、Chain-Shu Hsu

  DOI：10.1021/ja100236b

  日期：2010.4.7

  the ZnO interface. Moreover, this promising approach can be applied to another inverted solar cell, ITO/ZnO/C-PCBSD/PCPDTBT:PC(71)BM/PEDOT:PSS/Ag, using PCPDTBT as the p-type low-band-gap conjugated polymer to achieve an improved PCE of 3.4%. Incorporation of this cross-linked C(60) interlayer could become a standard procedure in the fabrication of highly efficient and stable multilayer inverted solar

  一种新型的基于 PCBM 的 n 型材料，[6,6]-苯基-C(61)-丁酸苯乙烯树枝状酯 (PCBSD)，用含有两个苯乙烯基的树枝作为热交联剂进行了功能化，已被合理设计和容易合成。PCBSD 的原位交联是通过在 160 摄氏度的低温下加热 30 分钟来进行的，以生成坚固、粘性和耐溶剂的薄膜。这种交联网络使连续的活性层能够成功地沉积在该中间层的顶部，以克服界面腐蚀的问题，并通过全溶液处理实现多层倒置器件。基于 ITO/ZnO/C-PCBSD/P3HT:PCBM/PEDOT:PSS/Ag 配置的倒置太阳能电池器件不仅实现了增强的器件特性，具有令人印象深刻的 4.4% 的 PCE，而且在没有封装的情况下也表现出非凡的器件寿命；它大大优于基于 ITO/ZnO/P3HT:PCBM/PEDOT:PSS/Ag 配置而没有中间层的参考器件 (PCE = 3.5%)。这种 C-PCBSD 夹层对有源层界面处的
• Highly Thermal Stable and Efficient Organic Photovoltaic Cells with Crosslinked Networks Appending Open-Cage Fullerenes as Additives
  作者：Chih-Ping Chen、Chien-Yu Huang、Shih-Ching Chuang

  DOI：10.1002/adfm.201401735

  日期：2015.1

  Highly thermal stable organic bulk heterojunction (OBHJ) photovoltaic cells are demonstrated with crosslinkable open‐cage fullerenes (COF) as additives in the active layer. Partial incorporation of COF, ≈10–15 wt% with weight ratio of P3HT:PC61BM = 1:0.9, builds up three‐dimensional local borders upon heating treatment at 150 °C for 10 min. This process induces crosslinking chemical reaction through

  展示了具有高热稳定性的有机体异质结（OBHJ）光伏电池，并在活性层中添加了可交联的开架式富勒烯（COF）作为添加剂。COF的部分掺入，≈10-15wt％，P3HT：PC 61 BM = 1：0.9的重量比，在150°C热处理10分钟时会建立三维局部边界。该过程通过活化COF中的苯乙烯基部分诱导了交联化学反应，并降低了富勒烯材料的相聚集速率。通过对设备性能下降数据的统计分析和光学显微镜研究的支持，具有COF的设备在延长使用寿命的同时仍保持了效率（t= 144 h）在150°C下的加速加热测试下，而没有COF的普通设备的PCE急剧下降。这些结果表明，可热交联的COF是高度热稳定和耐用的OPV应用的极好添加剂。
• Taddol and titanium (IV) taddolate dendrimers
  申请人：Novartis AG

  公开号：US06211316B1

  公开（公告）日：2001-04-03

  TADDOL dendrimers are described. Their use as crosslinkers in polymerisation reactions and the use of Ti salts of polymer-bound TADDOL dendrimers as catalysts in enantioselective addition reactions is disclosed.

  本文介绍了TADDOL树枝状聚合物。它们作为聚合反应中的交联剂以及聚合物支持的TADDOL树枝状聚合物的Ti盐在对映选择性加成反应中作为催化剂的使用被揭示。
• Synthesis of periphery-functionalized dendritic polyethers
  作者：Enrique Dı́ez-Barra、Raquel González、Prado Sánchez-Verdú、Juan Tolosa

  DOI：10.1016/j.tet.2003.12.003

  日期：2004.2

  New dendritic polyethers with bromo-, hydroxy- and vinyl-end groups have been synthesized by a convergent strategy. Planar, 1,3,5-trischlorocarbonylbenzene and 1,3,5-trihydroxybenzene, and tetrahedral, tetrakis(p-hydroxyphenyl)methane, cores have been used. (C) 2003 Elsevier Ltd. All rights reserved.
• Catalysis by titanocene-functionalized polymer-supported dendrimers
  作者：Patrick E. Berget、Jacqueline M. Teixeira、John L. Jacobsen、Neil E. Schore

  DOI：10.1016/j.tetlet.2007.09.115

  日期：2007.11

  A series of variously-functionalized first-, second-, and third-generation dendrimers have been prepared and linked via a biphenyl core to a bis-styryl moiety suitable for use as a crosslinker in polymerization. Attachment of titanocene moieties to the first-generation system and copolymerization with styrene affords polymeric disks that exhibit catalytic properties superior to comparable solution-phase systems in a multicomponent coupling of chlorosilanes with Grignards to give bis-allylic silanes. (c) 2007 Elsevier Ltd. All rights reserved.