1-(3-Bromopropoxy)-3,5-bis[3-(4-tert-butylphenoxy)propoxy]benzene | 176216-57-2

• 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-(3-Bromopropoxy)-3,5-bis[3-(4-tert-butylphenoxy)propoxy]benzene
• CAS: 176216-57-2
• 化学式: C₃₅H₄₇BrO₅
• 分子量: 627.659
• InChiKey: KRZAZOSMVMQVIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  41
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-Bromopropoxy)-3,5-bis[3-(4-tert-butylphenoxy)propoxy]benzene 在 18-冠醚-6 、 四溴化碳 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 1,3-bis[3-[3,5-bis[3-(4-tert-butylphenoxy)propoxy]phenoxy]propoxy]-5-(3-bromopropoxy)benzene
  参考文献：
  名称：

  An accelerated, improved synthetic route for the preparation of polyether-based dendritic fragments

  摘要：

  An accelerated, improved synthetic strategy for the rapid construction of two different series of polyether-based dendritic fragments is described. Several modifications to;the original method for the preparation of these dendritic fragments are detailed. A new branching agent, 5-(3-hydroxypropyloxy)1,3-resorcinol 4, instead of 5-benzyloxy-1,3-resorcinol 2, is employed in this new synthetic protocol. As a result, the number of synthetic operations in each of the iterative cycle is reduced from three to two, as compared to the original procedure. Each iterative synthetic cycle involves two reactions: a bis-O-alkylation reaction of the brancher 4 with a dendritic bromide [Gn]-O(CH2)(3)Br to give a dendritic alcohol of the next generation [G(n+1)]-O(CH2)(3)OH; followed by a functional group conversion of the dendritic alcohol into the corresponding dendritic bromide [G(n+1)]-O(CH2)(3)Br of the same generation. The reaction yields of each iterative cycle are consistently higher than those of the previously reported three step cycle. Using this new protcol, the preparation of a 5th generation dendritic alcohol 15a could be realized in 10 steps and 23% overall yields from 1,3-dibromopropane. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00851-5
• 作为产物：
  描述：

  3-[3,5-Bis[3-(4-tert-butylphenoxy)propoxy]phenoxy]propan-1-ol 在 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以96%的产率得到1-(3-Bromopropoxy)-3,5-bis[3-(4-tert-butylphenoxy)propoxy]benzene
  参考文献：
  名称：

  An accelerated, improved synthetic route for the preparation of polyether-based dendritic fragments

  摘要：

  An accelerated, improved synthetic strategy for the rapid construction of two different series of polyether-based dendritic fragments is described. Several modifications to;the original method for the preparation of these dendritic fragments are detailed. A new branching agent, 5-(3-hydroxypropyloxy)1,3-resorcinol 4, instead of 5-benzyloxy-1,3-resorcinol 2, is employed in this new synthetic protocol. As a result, the number of synthetic operations in each of the iterative cycle is reduced from three to two, as compared to the original procedure. Each iterative synthetic cycle involves two reactions: a bis-O-alkylation reaction of the brancher 4 with a dendritic bromide [Gn]-O(CH2)(3)Br to give a dendritic alcohol of the next generation [G(n+1)]-O(CH2)(3)OH; followed by a functional group conversion of the dendritic alcohol into the corresponding dendritic bromide [G(n+1)]-O(CH2)(3)Br of the same generation. The reaction yields of each iterative cycle are consistently higher than those of the previously reported three step cycle. Using this new protcol, the preparation of a 5th generation dendritic alcohol 15a could be realized in 10 steps and 23% overall yields from 1,3-dibromopropane. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00851-5

文献信息

• Synthesis and properties of a new class of polyether dendritic fragments: Useful building blocks for functional dendrimers
  作者：Hak-Fun Chow、Ida Yuk-Kit Chan、Chi Ching Mak、Man-Kit Ng

  DOI：10.1016/0040-4020(96)00088-9

  日期：1996.3

  solubility properties and are inert in both acidic and basic media, and do not show any redox behaviour from −2.0 to +1.9 V. Hence they are useful dendritic building blocks for the preparation of functional dendrimers.

  第一代至第四代的聚醚树枝状分子1-4是通过收敛方法从容易获得的4-叔丁基苯酚，间苯三酚和1,3-二溴丙烷中制备的。使用涉及三个步骤迭代合成序列的单ö [GN] -OH与过量的1,3-二溴丙烷烷基化，双- ö与5- benzyloxyresorcinol得到的化合物的烷基化5然后用钯催化剂进行氢解，可以以较高的收率制备下一代更高的[G（n + 1）]-OH。这些树枝状分子具有良好的溶解性，并且在酸性和碱性介质中均呈惰性，并且在-2.0至+1.9 V范围内没有任何氧化还原行为。因此，它们是制备功能性树枝状聚合物的有用的树枝状结构单元。
• An accelerated, improved synthetic route for the preparation of polyether-based dendritic fragments
  作者：Hak-Fun Chow、Zhao-Yang Wang、Yam-Fat Lau

  DOI：10.1016/s0040-4020(98)00851-5

  日期：1998.11

  An accelerated, improved synthetic strategy for the rapid construction of two different series of polyether-based dendritic fragments is described. Several modifications to;the original method for the preparation of these dendritic fragments are detailed. A new branching agent, 5-(3-hydroxypropyloxy)1,3-resorcinol 4, instead of 5-benzyloxy-1,3-resorcinol 2, is employed in this new synthetic protocol. As a result, the number of synthetic operations in each of the iterative cycle is reduced from three to two, as compared to the original procedure. Each iterative synthetic cycle involves two reactions: a bis-O-alkylation reaction of the brancher 4 with a dendritic bromide [Gn]-O(CH2)(3)Br to give a dendritic alcohol of the next generation [G(n+1)]-O(CH2)(3)OH; followed by a functional group conversion of the dendritic alcohol into the corresponding dendritic bromide [G(n+1)]-O(CH2)(3)Br of the same generation. The reaction yields of each iterative cycle are consistently higher than those of the previously reported three step cycle. Using this new protcol, the preparation of a 5th generation dendritic alcohol 15a could be realized in 10 steps and 23% overall yields from 1,3-dibromopropane. (C) 1998 Elsevier Science Ltd. All rights reserved.