3-(4-Vinylbenzyloxy)benzyl bromide | 312767-12-7

• 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: 3-(4-Vinylbenzyloxy)benzyl bromide
• 英文别名: 1-(Bromomethyl)-3-[(4-ethenylphenyl)methoxy]benzene；1-(bromomethyl)-3-[(4-ethenylphenyl)methoxy]benzene
• CAS: 312767-12-7
• 化学式: C₁₆H₁₅BrO
• 分子量: 303.198
• InChiKey: CUJKPTVVGFYZEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(4-Vinylbenzyloxy)benzyl bromide 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.08h， 生成 6-[[3-[(4-Ethenylphenyl)methoxy]phenyl]methoxy]-1-[6-[[3-[(4-ethenylphenyl)methoxy]phenyl]methoxy]-2-hydroxynaphthalen-1-yl]naphthalen-2-ol
  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-羟基苯甲醇 在 三溴化磷 、 potassium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 3-(4-Vinylbenzyloxy)benzyl bromide
  参考文献：
  名称：

  水溶性肽超分子编码的酸性肽

  摘要：

  肽的序列特异性识别在许多化学和生物学应用中具有极其重要的意义，但由于氨基酸侧链的微小差异而难以实现。已知酸性肽在细胞生长和基因表达中起重要作用。在这项工作中，我们报告分子印迹的胶束，其编码带有酸性肽的酸性和疏水性侧链的分子识别信息。印迹受体可以将酸性氨基酸与其他极性和非极性氨基酸区分开，对于包含多达18个氨基酸的生物活性肽，其解离常数为数十纳摩尔。

  DOI：

  10.1002/chem.201703760

文献信息

• Preparation of Polystyrene Beads with Dendritically Embedded TADDOL and Use in EnantioselectiveLewis Acid Catalysis
  作者：Holger Sellner、P. Beat Rheiner、Dieter Seebach

  DOI：10.1002/1522-2675(200201)85:1<352::aid-hlca352>3.0.co;2-d

  日期：2002.1

  of TADDOLates, which are dendritically incorporated in polystyrene beads (Scheme 1). A series of styryl-substituted TADDOLs with flexible, rigid, or dendritically branching spacers between the TADDOL core and the styryl groups (2–16 in number) has been prepared (5–7, 20, 21, 26 in Schemes 2–4 and Fig. 1–3). These were used as cross-linkers in styrene-suspension polymerization, leading to beads of ca

  对 TADDOLates 的制备和使用进行了完整的说明，TADDOLates 以树枝状掺入聚苯乙烯珠粒中（方案 1）。已经制备了一系列苯乙烯基取代的 TADDOL，在 TADDOL 核心和苯乙烯基（数量为 2-16）之间具有柔性、刚性或树枝状支化间隔物（方案 2-4 中的 5-7、20、21、26 和图 1-3)。这些被用作苯乙烯悬浮聚合中的交联剂，导致约珠。400-μm 直径（方案 5 和 6，b）。这些依次负载钛酸盐并用于路易斯酸催化将 Et2Zn 添加到 PhCHO 作为测试反应（方案 6）。在标准条件下获得的对映选择性和转化度（均高达 99%）的比较，表明这些掺入聚合物的 Ti-TADDOLates 是该过程的高效催化剂（表 1）。鉴于制备新型固定化催化剂所需的努力，重点放在了它们的多种用途上。从 TADDOL 获得的聚合物在 20 次测试反应循环中的性能最好，该聚合物带有四个第一代
• 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
  作者：Holger Sellner、Claude Faber、P. Beat Rheiner、Dieter Seebach

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

  日期：2000.10.16

  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.
• Water-Soluble Nanoparticle Receptors Supramolecularly Coded for Acidic Peptides
  作者：Shixin Fa、Yan Zhao

  DOI：10.1002/chem.201703760

  日期：2018.1.2

  recognition of peptides is of enormous importance to many chemical and biological applications, but has been difficult to achieve due to the minute differences in the side chains of amino acids. Acidic peptides are known to play important roles in cell growth and gene expression. In this work, we report molecularly imprinted micelles coded with molecular recognition information for the acidic and hydrophobic

  肽的序列特异性识别在许多化学和生物学应用中具有极其重要的意义，但由于氨基酸侧链的微小差异而难以实现。已知酸性肽在细胞生长和基因表达中起重要作用。在这项工作中，我们报告分子印迹的胶束，其编码带有酸性肽的酸性和疏水性侧链的分子识别信息。印迹受体可以将酸性氨基酸与其他极性和非极性氨基酸区分开，对于包含多达18个氨基酸的生物活性肽，其解离常数为数十纳摩尔。