2-(2-methoxyphenyl)benzyl bromide | 19853-13-5

• 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: 2-(2-methoxyphenyl)benzyl bromide
• 英文别名: 2'-bromomethyl-2-methoxybiphenyl；2-bromomethyl-2'-methoxybiphenyl；2'-Brommethyl-2-methoxy-biphenyl；1-(Bromomethyl)-2-(2-methoxyphenyl)benzene
• CAS: 19853-13-5
• 化学式: C₁₄H₁₃BrO
• 分子量: 277.161
• InChiKey: KMLAXRUMOBERHL-UHFFFAOYSA-N

物化性质

• 沸点：
  347.9±30.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  2-(2-methoxyphenyl)benzyl bromide 在 正丁基锂 、 indium(III) bromide 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 为溶剂， 反应 65.0h， 生成 10-butyl-4-methoxyphenanthrene
  参考文献：
  名称：

  通过In（III）催化的6- Exo - Dig环异构化方便地合成菲

  摘要：

  本文介绍了In（III）催化邻炔丙基联芳基的选择性6- exo - dig加氢芳基化反应及其随后的双键迁移以获得官能化菲的第一个实例。富电子的联芳基底物更有效地进行氢芳基化，并且在炔烃上具有各种取代基的底物也可以平稳且选择性地转化为菲。

  DOI：

  10.1021/ol400073s
• 作为产物：
  描述：

  2-(2'-methoxyphenyl)benzyl alcohol 在 四溴化碳 、 三苯基膦 作用下， 以 乙腈 为溶剂， 以98%的产率得到2-(2-methoxyphenyl)benzyl bromide
  参考文献：
  名称：

  通过In（III）催化的6- Exo - Dig环异构化方便地合成菲

  摘要：

  本文介绍了In（III）催化邻炔丙基联芳基的选择性6- exo - dig加氢芳基化反应及其随后的双键迁移以获得官能化菲的第一个实例。富电子的联芳基底物更有效地进行氢芳基化，并且在炔烃上具有各种取代基的底物也可以平稳且选择性地转化为菲。

  DOI：

  10.1021/ol400073s

文献信息

• Design of bifunctional quaternary phosphonium salt catalysts for CO₂ fixation reaction with epoxides under mild conditions
  作者：Shiyao Liu、Naoki Suematsu、Keiji Maruoka、Seiji Shirakawa

  DOI：10.1039/c6gc01630h

  日期：——

  An efficient synthesis of cyclic carbonates from epoxides and CO2 under mild reaction conditions was achieved via the use of a newly designed bifunctional quaternary phosphonium iodide catalyst. The importance...

  通过使用新设计的双功能四级碘化季phospho催化剂，可以在温和的反应条件下从环氧化物和CO2有效合成环状碳酸酯。重要性...
• Inhibition of Nucleoside Transport by New Analogues of 4-Nitrobenzylthioinosine:  Replacement of the Ribose Moiety by Substituted Benzyl Groups
  作者：Reynier A. Tromp、Susan van Ameijde、Claudia Pütz、Corinna Sundermann、Bernd Sundermann、Jacobien K. von Frijtag Drabbe Künzel、Adriaan P. IJzerman

  DOI：10.1021/jm049735v

  日期：2004.10.1

  4-Nitrobenzylthioinosine (NBTI, 1) is a well-known inhibitor for the nucleoside transport protein ENT1. However, its highly polar nature is unfavorable for oral absorption and/or penetration into the CNS. In the search for compounds with lower polarity than NBTI we replaced its ribose moiety by substituted benzyl groups. Halogen, hydroxyl, (trifluoro)methyl(-oxy), nitro, and amine functionalities were among the substituents at the benzyl group. In general, substitution of the benzyl group resulted in a lower affinity for ENT1. Only 2-hydroxyl substitution showed a higher affinity. Most likely this is the result of hydrogen bonding. Substitution at the 2-position of the benzyl group with aryl groups was also addressed. Compared to parent compound carrying a 2-phenylbenzyl group, all synthesized analogues gave higher affinities. Introduction of fluoro, trifluoromethyl, methoxy, and hydroxyl groups at the phenyl group clearly showed that addition to the 4-position was preferable. Despite the highly different character of a ribose and a benzyl group, K-i values in the low nanomolar range were obtained for the benzyl-substituted derivatives. Compound 35, LUF5919, and compound 60, LUF5929, displayed the highest affinity (K-i = 39 nM for both compounds), having a polar surface area of 101 Angstrom(2) and 85 Angstrom(2), respectively.
• Orientation and Alkylation Effects on Cation-π Interactions in Aqueous Solution
  作者：Mark J. Rashkin、Robert M. Hughes、Nathaniel T. Calloway、Marcey L. Waters

  DOI：10.1021/ja0498538

  日期：2004.10.1

  We have investigated the orientation dependence of the cation-pi interaction between a phenyl ring and a pyridinium ring in the context of a flexible model system in water. Of the four possible positions of the pyridinium nitrogen, ipso, ortho, meta, and para, we found a variation in the interaction energy of about 0.75 kcal mol(-1), with the stacking of the ipso-pyridinium ring providing the strongest interaction. The observed stability is attributed to the maximization of the electrostatic interaction, minimization of rotamers, and possible differences in hydration phenomena arising from alkylation.