1,2-bis(benzyloxy)-3-(bromomethyl)benzene | 81464-85-9

• 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: 1,2-bis(benzyloxy)-3-(bromomethyl)benzene
• 英文别名: 1,1'-{[3-(Bromomethyl)-1,2-phenylene]bis(oxymethylene)}dibenzene；1-(bromomethyl)-2,3-bis(phenylmethoxy)benzene
• CAS: 81464-85-9
• 化学式: C₂₁H₁₉BrO₂
• 分子量: 383.285
• InChiKey: OBKKWHHFLMHDGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-bis(benzyloxy)-3-(bromomethyl)benzene 在 palladium on activated charcoal 吡啶 、 喹啉 、 lithium aluminium tetrahydride 、 二溴亚砜 、 potassium tert-butylate 、 氢气 、 potassium carbonate 、 copper(II) oxide 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 、 丙酮 、 苯 为溶剂， 170.0 ℃ 、101.33 kPa 条件下， 反应 25.25h， 生成 6,6,35,35-tetramethyl-2,5,7,18,31,34,36,47-octaoxaundecacyclo[54.2.2.227,30.13,10.113,17.132,39.142,46.04,8.019,24.033,37.048,53]hexahexaconta-1(58),3,8,10(66),13(65),14,16,19(24),20,22,27(64),28,30(63),32,37,39(62),42(61),43,45,48(53),49,51,56,59-tetracosaene-20,49-diol
  参考文献：
  名称：

  Total syntheses of marchantin A and riccardin B, cytotoxic bis(bibenzyls) from liverworts

  摘要：

  DOI：

  10.1021/jo00236a015
• 作为产物：
  描述：

  2,3-二苄氧基苯甲醛 在 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 四氢呋喃 为溶剂， 生成 1,2-bis(benzyloxy)-3-(bromomethyl)benzene
  参考文献：
  名称：

  旨在同时结合碱金属离子和过渡金属阳离子的大环ditopic受体的合成

  摘要：

  带有两个邻苯二酚基团的二氮杂四氧环环十八烷衍生物的合成产率很高。设计双核配体以同时结合软阳离子和硬阳离子。

  DOI：

  10.1016/0040-4039(94)80116-9

文献信息

• Oxidative Metabolism of the Mammalian Lignans Enterolactone and Enterodiol by Rat, Pig, and Human Liver Microsomes
  作者：Eric Jacobs、Manfred Metzler

  DOI：10.1021/jf9809176

  日期：1999.3.1

  microsomes from aroclor-treated male Wistar rats biotransform enterolactone to 12 metabolites, six of which carry an additional hydroxy group at the aromatic and six at the aliphatic moiety according to HPLC/MS and GC/MS analysis. The aromatic hydroxylation products were identified with the help of synthesized reference compounds as enterolactone monohydroxylated in the para position and in both ortho positions

  根据HPLC / MS和GC / MS分析，用acrolor处理的雄性Wistar大鼠的肝微粒体将肠内酯生物转化为12种代谢物，其中6种在芳族上带有一个额外的羟基，在脂族部分上带有6个羟基。借助于合成的参考化合物，芳族羟基化产物鉴定为肠内酯在任一芳族环的原始酚羟基的对位和两个邻位均被单羟基化。描述了参考化合物的合成及其光谱表征。肠糖被肝微粒体从经aroclor处理的雄性大鼠代谢为三种芳香族和四种脂肪族单羟基化代谢产物。芳族羟基化发生在原始酚羟基的对位和两个邻位。
• Borocryptands : Synthesis and Structural Analysis of a Lithium Borocryptate
  作者：Frédéric Bockstahl、Ernest Graf、Mir Wais Hosseini、Dominique Suhr、André De Cian、Jean Fischer

  DOI：10.1016/s0040-4039(97)10026-0

  日期：1997.10

  A new lithium receptor based on the combination of the [11] macrocyclic core and two catechol units was designed and prepared. The binding ability of the ligand towards boron and lithium was demonstrated in solution by NMR and in the solid state by an X-ray analysis of the lithiumborocryptate. © 1997 Elsevier Science Ltd.

  设计并制备了一种基于[11]大环核和两个邻苯二酚单元的新型锂受体。通过NMR在溶液中和在固态通过硼硼酸锂的X射线分析证明了配体对硼和锂的结合能力。©1997爱思唯尔科学有限公司。
• Total synthesis of marchantin A, a novel cytotoxic bis(bibenzyl) isolated from liverworts
  作者：Mitsuaki Kodama、Yoshinori Shiobara、Katsuki Matsumura、Hisako Sumitomo

  DOI：10.1016/s0040-4039(00)61953-6

  日期：——

  Total synthesis of marchantin A, a novel cytotoxic bis(bibenzyl) isolated from some liverworts, has been accomplished in 12 steps.

  从一些地草中分离出的新型细胞毒性双（联苄）marchantin A的总合成已通过12个步骤完成。
• Towards Responsive Spiroborate‐Based Assemblies of Podand‐Type Ligands Functionalized with Two Terminal/Peripheral Catecholate Moieties in the Presence of Alkali Cations
  作者：Maxime Florent、Florine Witt、Audrey Fluck、Nathalie Kyritsakas、Jean‐Marc Planeix、Aurélie Guenet、Mir Wais Hosseini

  DOI：10.1002/ejoc.202300773

  日期：2024.2.19

  Flexible bis-catecholate podand-type ligands of various lengths were synthesized. Upon reaction with boric acid and a hydroxide alkaline solution, a spiroborate node forms and the alkali cation is wrapped by the flexible spacer. Influence of the spacer's length and the alkali cation size on the formation of monomeric or oligomeric spiroborate compounds was studied in solution by DOSY NMR.

  合成了各种长度的柔性双儿茶酚酸荚型配体。与硼酸和氢氧化物碱性溶液反应后，形成螺硼酸盐节点，并且碱性阳离子被柔性间隔基包裹。通过 DOSY NMR 在溶液中研究了间隔基长度和碱金属阳离子尺寸对单体或低聚螺硼酸盐化合物形成的影响。
• Double-head haptens. Synthesis of and experimentally induced contact sensitivity to substances containing two unrelated haptens, pyrocatechol and .alpha.-methylene-.gamma.-butyrolactone, in the same molecule
  作者：Bernard Marchand、Claude Benezra

  DOI：10.1021/jm00348a008

  日期：1982.6

  A "double-head" hapten containing a pyrocatechol and an alpha-methylene-gamma-butyrolactone moiety (3) and "monofunctional haptens" with either one of these moieties (18 and 19) connected by a six-carbon chain have been synthesized, and their sensitizing capacity was tested on guinea pigs. In the "double-head" hapten, only the pyrocatechol end is "recognized". A possible interpretation of the biological results is offered.