1,2,4,5-tetrakis(bromomethyl)-3,6-bis(hexyloxy)benzene | 117408-76-1

• 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: 1,2,4,5-tetrakis(bromomethyl)-3,6-bis(hexyloxy)benzene
• 英文别名: 1,2,4,5-tetrakis(bromomethyl)-3,6-dihexoxybenzene
• CAS: 117408-76-1
• 化学式: C₂₂H₃₄Br₄O₂
• 分子量: 650.127
• InChiKey: YULCSLCFZAOWNP-UHFFFAOYSA-N

物化性质

• 沸点：
  565.0±45.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  1,2,4,5-tetrakis(bromomethyl)-3,6-bis(hexyloxy)benzene 在 过氧乙酸 、 sodium sulfide 作用下， 反应 3.0h， 生成 4,8-Bis-hexyloxy-5,7-dihydro-1H,3H-benzo[1,2-c;4,5-c']dithiophene 2,2,6,6-tetraoxide
  参考文献：
  名称：

  重复的狄尔斯-阿尔德反应：[60]富勒烯主链聚合物的新方法

  摘要：

  结合有[60]富勒烯单元的Maindashchain聚合物可通过buckminsterfullerene与官能化的反应来获得。仔细指导混合可以有效地抑制交联。具有平均分子量为80 [60]富勒烯单元的高分子量和优异溶解性的聚合物11（n）价格适中。可以通过旋涂将该聚合物加工成高质量的非晶态薄膜。

  DOI：

  10.1016/0040-4020(96)00108-1
• 作为产物：
  描述：

  四甲基氢醌 在 N-溴代丁二酰亚胺(NBS) 、 sodium ethanolate 作用下， 以 四氯化碳 、 乙醇 为溶剂， 反应 6.0h， 生成 1,2,4,5-tetrakis(bromomethyl)-3,6-bis(hexyloxy)benzene
  参考文献：
  名称：

  A donor-type cyclophane with a strongly bent tetrathiafulvalene unit

  摘要：

  DOI：

  10.1021/jo00034a033

文献信息

• Redox responsive molecular tweezers with tetrathiafulvalene units: synthesis, electrochemistry, and binding properties
  作者：Maciej Skibiński、Rafael Gómez、Enno Lork、Vladimir A. Azov

  DOI：10.1016/j.tet.2009.10.052

  日期：2009.12

  Several new molecular tweezers with tetrathiafulvalene (TTF) arms as well as mono-TTF derivatives bearing 3,5-di-tert-butylbenzylthio groups to provide enhanced solubility were prepared starting from a bis-cyanoethyl-protected tetrathiafulvalene derivative. The X-ray crystallographic analysis of 3 and 7a showed highly distorted TTF groups and absence of close TTF-TTF contacts in the crystalline state. Comparative cyclic voltammetry (CV) measurements demonstrated that through space distance-dependent TTF-TTF interactions take place in the TTF-containing molecular tweezers, leading to electronic pairing with formation of mixed valence [TTF](2)(+center dot) species and splitting of the first oxidation wave. TTF-containing molecular tweezers were successfully tested as receptors for several electron-deficient substances. (C) 2009 Elsevier Ltd. All rights reserved.
• Conformational control of flexible molecular tweezers by intramolecular CH/π interaction
  作者：Hajime Iwamoto、Nobuaki Takahashi、Takuma Maeda、Yusuke Hidaka、Yoshimasa Fukazawa

  DOI：10.1016/j.tetlet.2005.08.016

  日期：2005.10

  The synthesis of new flexible molecular tweezers based on 3,4,8,10,11,13-hexahydro-1H,6H-2,5,9,12-tetraoxabenzo[1,2:4,5]dicyclooctene bearing two naphthalenes is presented. Intratnolecular CH/pi interaction between the alkyl ring and the two terminal naphthalenes controls the conformation to give a self-quenched cleft form. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis of electrochemically responsive TTF-based molecular tweezers: evidence of tight intramolecular TTF pairing in solution
  作者：Vladimir A. Azov、Rafael Gómez、Johannes Stelten

  DOI：10.1016/j.tet.2007.11.110

  日期：2008.2

  We report the synthesis and conformational studies of TTF-containing molecular tweezers based on a 1,2,4,5-tetramethylbenzene scaffold. In the neutral form the tweezers are expected to adopt the closed conformation, while, upon oxidation, the open conformation should be preferred due to electrostatic repulsion between the oxidized TTF moieties. Cyclic voltammetry studies demonstrate electronic pairing with formation of mixed-valence [TTF](2)(+center dot) species and opening of the tweezers upon the full oxidation of the TTF groups. Variable-temperature (VT) NMR studies evidence tight intramolecular TTF pairing at low temperature. Molecular modeling studies showed clear preference for an open conformation of tweezers in a fully oxidized state. (C) 2007 Elsevier Ltd. All rights reserved.
• Roehrich, Joerg; Wolf, Peter; Enkelmann, Volker, Angewandte Chemie, 1988, vol. 100, # 10, p. 1429 - 1430
  作者：Roehrich, Joerg、Wolf, Peter、Enkelmann, Volker、Muellen, Klaus

  DOI：——

  日期：——
• A donor-type cyclophane with a strongly bent tetrathiafulvalene unit
  作者：J. Roehrich、K. Muellen

  DOI：10.1021/jo00034a033

  日期：1992.4