4,4''-Bis-bromomethyl-(1,1',3',1'')terphenyl-2'-carboxylic acid | 155186-09-7

• 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: 4,4''-Bis-bromomethyl-(1,1',3',1'')terphenyl-2'-carboxylic acid
• 英文别名: 2,6-bis[4-(bromomethyl)phenyl]benzoic acid
• CAS: 155186-09-7
• 化学式: C₂₁H₁₆Br₂O₂
• 分子量: 460.165
• InChiKey: YGHVNSPBHKPTSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4''-Bis-bromomethyl-(1,1',3',1'')terphenyl-2'-carboxylic acid 在 吡啶 、 氢氧化钾 、 氯化亚砜 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 18,27-Dioxa-12,33-dithiaheptacyclo[33.2.2.27,10.214,17.228,31.12,6.020,25]hexatetraconta-1(37),2(46),3,5,7(45),8,10(44),14(43),15,17(42),20,22,24,28,30,35,38,40-octadecaene-46-carbonyl chloride
  参考文献：
  名称：

  Synthesis of Cyclophanes with Intra-Annular Functionality and Cage Structure

  摘要：

  Cyclophanes of the type 1 and 2, with large cavity sizes, have been synthesized from the corresponding dichloride 8 or 8a and o-xylene-alpha,alpha'-dithiol (9), p-xylene-alpha,alpha'-dithiol (10), or m-terphenyldithiol (11). Similarly, cyclophanes of the type 3 with intra-annular functionality have been obtained by the coupling of the corresponding dithiol 15 or 19 and m-terphenyl dibromide 5, 5a, 5b, or 5c. With the aim of introducing multifunctionality, cyclophanes of the type 21 and 23 were prepared from 3,5-bis(mercaptomethyl)anisole or 3,5-bis(mercaptomethyl)phenol and the corresponding substituted m-terphenyl dibromide Bb or 5c. Cyclophanes 24, 24a, 24b, and 32, with a new type of cage structure, have been obtained by the coupling of the corresponding tetrathiol as with 2 equiv of the dibromides 5c, 5a, and 5b or 1 equiv of the tetrabromide 31, respectively. Further, the sodium salts of the cyclophanes 3c, 21, and 24b were completely characterized by H-1 NMR spectroscopy. XRD analysis of the cyclophane 21 revealed the presence of an ethanol molecule inside the cavity, indicating the facile formation of a host-guest complex.

  DOI：

  10.1021/jo950957y
• 作为产物：
  描述：

  2,6-双(4-甲基苯基)苯甲酸 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 40.0h， 以92%的产率得到4,4''-Bis-bromomethyl-(1,1',3',1'')terphenyl-2'-carboxylic acid
  参考文献：
  名称：

  2′-Substituted meta-terphenyls as building blocks for cyclophanes with intra-annular functionality

  摘要：

  2'-Substituted m-terphenyls containing chloromethyl and/or thiomethyl groups at the 4,4'' or 3,3'' positions are used as building blocks for cyclophanes with intra-annular functionality. Syntheses are short and yields are good. The methodology, capable of wide structural variation, has been adapted to bi- and tricyclic cyclophanes.

  DOI：

  10.1016/0040-4020(94)01016-s

文献信息

• Benzotriazolophanes—New Class of Novel Cyclophanes
  作者：Perumal Rajakumar、Venghatraghavan Murali

  DOI：10.1016/s0040-4020(00)00717-1

  日期：2000.9

  benzotriazole with 4,4″-bis(bromomethyl)-1,1′:3′,1″-terphenyl in two steps gave the unprecedented benzotriazolophane 4a. By similar alkylation procedure, cyclophanes 4b, 4c and 4d were obtained from the substituted dibromides 6b, 6c and 6d, respectively. Novel cross-linked benzotriazolophane 5 was obtained by using the tetrabromide 9 as the spacer unit.

  苯并三唑与各种二甲苯基二溴化物（o，m，p）或4,4'-双（溴甲基）联苯的两步烷基化反应得到苯并三唑并2或3。类似地，在两个步骤中将苯并三唑与4,4″-双（溴甲基）-1，1′：3′，1″-三联苯进行烷基化，得到了前所未有的苯并三唑烷4a。通过类似的烷基化方法，分别从取代的二溴化物6b，6c和6d获得环烷4b，4c和4d。新型交联的苯并三唑烷5通过使用四溴化物9作为间隔单元获得。
• Novel 4,4′-Bipyridinium-Based Cationic Mono- and Bicyclic Cyclophanes
  作者：Perumal Rajakumar、Kannupal Srinivasan

  DOI：10.1002/ejoc.200390183

  日期：2003.3

  a rare hexacationic cyclophane 18. The cyclophanes 3a and 3c form CT complexes with a bis(1H-indol-3-yl)(phenyl)methane compound while the cyclophane 13 forms CT complexes with 1,4-dimethoxybenzene and indole. Electrochemical parameters were obtained for all the cyclophanes. They exhibit two sets of redox peaks and most of them are quasireversible. The smallest-cavity cyclophane 13 has the lowest reduction

  通过简单的季铵化方法从相应的间三联苯二溴化物和 4,4'-联吡啶合成环内官能化的四阳离子环芳烃 3a-b。环内连接的四阳离子环芳烃 10 分三步合成，它具有凹形结构和新的分子内 CT 相互作用。含有羰基的四阳离子环芳烃 13、16a 和 16b 的合成由相应的羰基二溴化物和 4,4'-联吡啶完成。三羰基三溴化物与 4,4'-联吡啶的六重偶联得到罕见的六阳离子环芳 18。环芳 3a 和 3c 与双 (1H-吲哚-3-基)(苯基) 甲烷化合物形成 CT 配合物，而环芳 13 形成CT 与 1,4-二甲氧基苯和吲哚复合。获得了所有环芳烃的电化学参数。它们表现出两组氧化还原峰，其中大部分是准可逆的。最小腔的环芳烃 13 具有该系列中最低的还原电位。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Sodium sulfate supported synthesis of cationic cyclophanes using microwaves
  作者：Perumal Rajakumar、Venghatraghavan Murali

  DOI：10.1039/b109003h

  日期：2001.12.19

  A facile microwave-assisted synthesis of a series of cationic cyclophanes, viz. benzimidazolophanes 3a–3f, benzotriazolophanes 3g–3j, through efficient double quaternization of the corresponding precyclophanes 1a–1j with appropriate dibromides 2a–2d in solid phase medium, is described.

  一系列阳离子环烷的简便微波辅助合成，即。描述了苯并咪唑烷 3a-3f、苯并三唑烷 3g-3j，通过相应的前环烷 1a-1j 与适当的二溴化物 2a-2d 在固相介质中的有效双季铵化。
• Synthesis of functionalised cyclophanes with cage structure; via an unusual termolecular collision
  作者：Perumal Rajakumar、Arunachalam Kannan

  DOI：10.1016/s0040-4039(00)61420-x

  日期：1993.12

  Coupling of the tetrathiol 11 with two equivalents of the dibromide 6,7 and 8 under high dilution technique in the presence of KOH in benzene - ethanol afforded the cyclophanes 1a, 1c & 1b respectively. Similarly cyclophane 1d was obtained from the tetrathiol 11 and tetrabromide 9.
• Synthesis and Molecular Transformations of Functionalised Cyclophanes with Large Cavity
  作者：Arunachalam Kannan、Perumal Rajakumar

  DOI：10.1080/00397919508011438

  日期：1995.10

  Cyclophanes of the type 1 & 3 are obtained by the coupling of suitable dithiol with corresponding dibromide under high dilution technique in the presence of KOH in benzene or toluene-ethanol. Few molecular transformations have been effected on the cyclophanes 1 and 2.