4-[5-[3,4-Bis(bromomethyl)phenoxy]pentoxy]-1,2-bis(bromomethyl)benzene | 186843-22-1

• 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: 4-[5-[3,4-Bis(bromomethyl)phenoxy]pentoxy]-1,2-bis(bromomethyl)benzene
• CAS: 186843-22-1
• 化学式: C₂₁H₂₄Br₄O₂
• 分子量: 628.036
• InChiKey: CQDZLOZYZROKHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  足球烯 、 4-[5-[3,4-Bis(bromomethyl)phenoxy]pentoxy]-1,2-bis(bromomethyl)benzene 在 18-冠醚-6 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以30%的产率得到67,73-Dioxahexatriacontacyclo[43.31.2.111,14.113,17.155,63.162,66.174,77.03,28.03,45.04,26.05,43.06,24.07,42.08,39.09,23.010,38.012,22.015,34.016,32.018,30.019,27.021,25.029,47.031,48.033,50.035,52.037,53.040,54.041,56.044,57.046,58.049,59.051,60.055,60.020,82.036,83]trioctaconta-1(77),4(26),5,7,9,11(83),12,14,16(32),17(82),18,20,22,24,27,29,31(48),33,35,37(53),38,40(54),41,43,46,49,51,56,58,62,64,66(80),74(79),75-tetratriacontaene
  参考文献：
  名称：

  Selective Functionalization on [60]Fullerene Governed by Tether Length

  摘要：

  In order to accomplish the selective synthesis of [60]fullerene bisadducts, the reactions of [60]fullerene with compounds in which two alpha,alpha'-dibromo-o-xylene moieties were connected by an oligomethylene chain (n = 2-5) were investigated. By this method, only two isomers (cis-2- and cis-3-isomers) were selectively obtained when n = 2 and 3, while another isomer (e-isomer) was obtained when n = 5. When n = 4, a complex mixture of bisadducts was formed and has not been separated so far. cis-2-Bisadducts have been, for the first time, selectively obtained in the fullerene chemistry. The structures of bisadducts were determined on the basis of H-1, C-13 NMR, IR, W-vis, and mass spectroscopies. According to the NMR experiments, the symmetries of cis-2-, cis-3-, and e-isomers were concluded to be C-s, C-2, and C-1, respectively. Chiral cis-3- and e-bisadducts were successfully resolved into the respective enantiomers on a chiral HPLC column, although cis-2-bisadducts only gave a single peak. The UV-vis spectra of cis-2-, cis-3-, and e-bisadducts were remarkably different from one another. Specifically, the e-bisadducts showed a characteristic absorption peak around 420 nm. The cleavage of the oligomethylene chain produced the corresponding [60]fullerene derivatives possessing two phenol moieties. These compounds are applicable to further functionalization.

  DOI：

  10.1021/ja960873m
• 作为产物：
  描述：

  4-羟基酞酸二甲酯 在 potassium fluoride 、 lithium aluminium tetrahydride 、 三溴化磷 作用下， 以 四氢呋喃 、 甲苯 、 乙腈 为溶剂， 生成 4-[5-[3,4-Bis(bromomethyl)phenoxy]pentoxy]-1,2-bis(bromomethyl)benzene
  参考文献：
  名称：

  Selective Functionalization on [60]Fullerene Governed by Tether Length

  摘要：

  In order to accomplish the selective synthesis of [60]fullerene bisadducts, the reactions of [60]fullerene with compounds in which two alpha,alpha'-dibromo-o-xylene moieties were connected by an oligomethylene chain (n = 2-5) were investigated. By this method, only two isomers (cis-2- and cis-3-isomers) were selectively obtained when n = 2 and 3, while another isomer (e-isomer) was obtained when n = 5. When n = 4, a complex mixture of bisadducts was formed and has not been separated so far. cis-2-Bisadducts have been, for the first time, selectively obtained in the fullerene chemistry. The structures of bisadducts were determined on the basis of H-1, C-13 NMR, IR, W-vis, and mass spectroscopies. According to the NMR experiments, the symmetries of cis-2-, cis-3-, and e-isomers were concluded to be C-s, C-2, and C-1, respectively. Chiral cis-3- and e-bisadducts were successfully resolved into the respective enantiomers on a chiral HPLC column, although cis-2-bisadducts only gave a single peak. The UV-vis spectra of cis-2-, cis-3-, and e-bisadducts were remarkably different from one another. Specifically, the e-bisadducts showed a characteristic absorption peak around 420 nm. The cleavage of the oligomethylene chain produced the corresponding [60]fullerene derivatives possessing two phenol moieties. These compounds are applicable to further functionalization.

  DOI：

  10.1021/ja960873m