5,14-Dioxa-4,15-dioxooctadeca-2,16-diene-1,18-dicarboxylic acid | 118495-79-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5,14-Dioxa-4,15-dioxooctadeca-2,16-diene-1,18-dicarboxylic acid
• 英文别名: (Z)-4-[8-[(Z)-3-carboxyprop-2-enoyl]oxyoctoxy]-4-oxobut-2-enoic acid
• CAS: 118495-79-7
• 化学式: C₁₆H₂₂O₈
• 分子量: 342.346
• InChiKey: BMBLWTPEFWJYDO-XOHWUJONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,14-Dioxa-4,15-dioxooctadeca-2,16-diene-1,18-dicarboxylic acid 在 哌啶 甲烷磺酸 作用下， 以 丙醇 、 苯 为溶剂， 反应 14.0h， 生成 3-(4-Hydroxy-1-thiabutyl)-1,6,15,20-tetraoxa-2,5,16,19-tetraoxocyclooctacos-17-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：

  马来酸酐 、 1,8-辛二醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以61 %的产率得到5,14-Dioxa-4,15-dioxooctadeca-2,16-diene-1,18-dicarboxylic acid
  参考文献：
  名称：

  高稀释条件下的连续流动分子间和分子内大内酯化

  摘要：

  在 Mukaiyama 试剂（ N -methyl-2-chloropyridinium iodide）存在的情况下，已开发出一种有效的连续流动工艺，用于使用二元醇对 seco 酸和二酸进行大环内酯化，用于中型到大型大环内酯。与其他方法相比，连续流动过程在较短的反应时间内提供了良好的高收率。通过使用这种方法，在短短 35 分钟的停留时间内合成了具有不同环大小（核心 12-26 个原子）的各种大环内酯（11 种化合物）、双内酯（15 种化合物）和四内酯衍生物（2 种化合物）时间。有利地，流动过程下的大环内酯化非常优雅地处理具有定义的全氟烷氧基烷烃（PFA）管反应器体积（7 mL）的反应物的高度稀释。

  DOI：

  10.1021/acs.joc.2c03000

文献信息

• Biomimetic ion transport: a functional model of a unimolecular ion channel
  作者：V. E. Carmichael、P. J. Dutton、T. M. Fyles、T. D. James、J. A. Swan、M. Zojaji

  DOI：10.1021/ja00184a075

  日期：1989.1
• 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.
• Continuous Flow Inter- and Intramolecular Macrolactonization under High Dilution Conditions
  作者：Dashrat Vishambar Sutar、Neha Uttamrao Sarang、Akash Bandu Jamdade、Boopathy Gnanaprakasam

  DOI：10.1021/acs.joc.2c03000

  日期：2023.3.17

  iodide) has been developed for medium to large sized macrocyclic lactones. In comparison with other methods, the continuous flow process provided good to high yield in a short reaction time. By using this methodology, a wide range of macrocyclic lactones (11 compounds), dilactones (15 compounds), and tetralactone derivatives (2 compounds) with various ring sizes (12–26 atoms in the core) were synthesized

  在 Mukaiyama 试剂（ N -methyl-2-chloropyridinium iodide）存在的情况下，已开发出一种有效的连续流动工艺，用于使用二元醇对 seco 酸和二酸进行大环内酯化，用于中型到大型大环内酯。与其他方法相比，连续流动过程在较短的反应时间内提供了良好的高收率。通过使用这种方法，在短短 35 分钟的停留时间内合成了具有不同环大小（核心 12-26 个原子）的各种大环内酯（11 种化合物）、双内酯（15 种化合物）和四内酯衍生物（2 种化合物）时间。有利地，流动过程下的大环内酯化非常优雅地处理具有定义的全氟烷氧基烷烃（PFA）管反应器体积（7 mL）的反应物的高度稀释。