5-(3-hydroxypropyloxy)-1,3-resorcinol | 216968-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-(3-hydroxypropyloxy)-1,3-resorcinol
• 英文别名: 5-(3-Hydroxypropoxy)benzene-1,3-diol
• CAS: 216968-13-7
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: AJBZODKQVPTFAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(3-hydroxypropyloxy)-1,3-resorcinol 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：

  1,3,5-三(苯基甲氧基)苯 在 palladium on activated charcoal 氢气 、 sodium hydride 、 potassium carbonate 、 乙硫醇 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 29.0h， 生成 5-(3-hydroxypropyloxy)-1,3-resorcinol
  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

• 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.