3-(4-Methylsulfonyl-1-thiabutyl)-1,6,12,17-tetraoxa-2,5,13,16-tetraoxocyclodicos-14-ene

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 3-(4-Methylsulfonyl-1-thiabutyl)-1,6,12,17-tetraoxa-2,5,13,16-tetraoxocyclodicos-14-ene
• 英文别名: 3-[[(14E)-2,5,13,16-tetraoxo-1,6,12,17-tetraoxacyclodocos-14-en-3-yl]sulfanyl]propyl methanesulfonate
• 化学式: C₂₂H₃₄O₁₁S₂
• 分子量: 538.637
• InChiKey: NITWHZFRLGMHEP-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  182
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  3-(4-Methylsulfonyl-1-thiabutyl)-1,6,12,17-tetraoxa-2,5,13,16-tetraoxocyclodicos-14-ene 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以55%的产率得到3-(4-Iodo-1-thiabutyl)-1,6,12,17-tetraoxa-2,5,13,16-tetraoxocyclodicos-14-ene
  参考文献：
  名称：

  Assembly of ion channel mimics from a modular construction set

  摘要：

  Ion channel mimics were assembled from a modular construction set consisting of core units, derived from polycarboxylate 18-crown-6 ethers, wall units, derived from macrocyclic tetraesters, and polar head groups which provide overall amphiphilic character. The preparation of symmetrical and side-discriminated macrocyclic tetraesters from diols and maleic anhydride gave the required macrocycles in low yields by acid-catalyzed esterification, or by carboxylate alkylation. Addition of 1 equiv of 3-mercaptopropanol to the macrocyclic dienes gave the wall unit precursor. Coupling of the walls to the crown ether via esters was achieved by carboxylate alkylation. The syntheses were completed by Michael addition of head group thiolates. Twenty-one candidate ion channels of molecular weight 1600-4800 g/mol were prepared and characterized.

  DOI：

  10.1021/jo00078a026
• 作为产物：
  描述：

  5,11-Dioxa-4,12-dioxopentadeca-2,13-diene-1,15-dicarboxylic acid 在 哌啶 甲烷磺酸 、 三乙胺 作用下， 以 丙醇 、 二氯甲烷 、 苯 为溶剂， 反应 16.0h， 生成 3-(4-Methylsulfonyl-1-thiabutyl)-1,6,12,17-tetraoxa-2,5,13,16-tetraoxocyclodicos-14-ene
  参考文献：
  名称：

  Assembly of ion channel mimics from a modular construction set

  摘要：

  Ion channel mimics were assembled from a modular construction set consisting of core units, derived from polycarboxylate 18-crown-6 ethers, wall units, derived from macrocyclic tetraesters, and polar head groups which provide overall amphiphilic character. The preparation of symmetrical and side-discriminated macrocyclic tetraesters from diols and maleic anhydride gave the required macrocycles in low yields by acid-catalyzed esterification, or by carboxylate alkylation. Addition of 1 equiv of 3-mercaptopropanol to the macrocyclic dienes gave the wall unit precursor. Coupling of the walls to the crown ether via esters was achieved by carboxylate alkylation. The syntheses were completed by Michael addition of head group thiolates. Twenty-one candidate ion channels of molecular weight 1600-4800 g/mol were prepared and characterized.

  DOI：

  10.1021/jo00078a026

文献信息

• Assembly of ion channel mimics from a modular construction set
  作者：Thomas M. Fyles、Tony D. James、Allana Pryhitka、Mohammad Zojaji

  DOI：10.1021/jo00078a026

  日期：1993.12

  Ion channel mimics were assembled from a modular construction set consisting of core units, derived from polycarboxylate 18-crown-6 ethers, wall units, derived from macrocyclic tetraesters, and polar head groups which provide overall amphiphilic character. The preparation of symmetrical and side-discriminated macrocyclic tetraesters from diols and maleic anhydride gave the required macrocycles in low yields by acid-catalyzed esterification, or by carboxylate alkylation. Addition of 1 equiv of 3-mercaptopropanol to the macrocyclic dienes gave the wall unit precursor. Coupling of the walls to the crown ether via esters was achieved by carboxylate alkylation. The syntheses were completed by Michael addition of head group thiolates. Twenty-one candidate ion channels of molecular weight 1600-4800 g/mol were prepared and characterized.