N,N'-dimethoxy-N,N'-dimethyl-[2,2'-bifuran]-5,5'-dicarboxamide | 380303-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: N,N'-dimethoxy-N,N'-dimethyl-[2,2'-bifuran]-5,5'-dicarboxamide
• 英文别名: N-methoxy-5-[5-[methoxy(methyl)carbamoyl]furan-2-yl]-N-methylfuran-2-carboxamide
• CAS: 380303-86-6
• 化学式: C₁₄H₁₆N₂O₆
• 分子量: 308.291
• InChiKey: TYLDLASYWJVWFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.81
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.36
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N,N'-dimethoxy-N,N'-dimethyl-[2,2'-bifuran]-5,5'-dicarboxamide 在 sodium tetrahydroborate 、 三苯基膦 、 肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 生成 (1R)-1-[5-[5-[(1S)-1-aminoundecyl]furan-2-yl]furan-2-yl]undecan-1-amine
  参考文献：
  名称：

  NOVEL CLASS OF DNA BINDING MOTIFS BASED ON BISTETRAHYDROFURAN AND BISFURAN SKELETON WITH LONG ALKYL CHAINS

  摘要：

  Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this paper, new DNA binding molecules; diamino-bistetrahydrofuran (bisTHF) and diamino-bisfuran are reported. The bisTHF ligand with RR configuration at the amino groups and C8 alkyl chains (RR8) stabilized GC-rich duplex. In contrast, bisfuran compounds stabilized AT-rich duplex. The binding affinity of RR8 with 12 mer duplex DNA was determined by isothermal titration calorimetry to be 3.3 x 10(8) M-1.

  DOI：

  10.1081/ncn-100002331
• 作为产物：
  描述：

  在 吡啶 、 sodium hydroxide 、 氯化亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N,N'-dimethoxy-N,N'-dimethyl-[2,2'-bifuran]-5,5'-dicarboxamide
  参考文献：
  名称：

  NOVEL CLASS OF DNA BINDING MOTIFS BASED ON BISTETRAHYDROFURAN AND BISFURAN SKELETON WITH LONG ALKYL CHAINS

  摘要：

  Small molecules with DNA-binding affinity within the minor groove have become of great interest. In this paper, new DNA binding molecules; diamino-bistetrahydrofuran (bisTHF) and diamino-bisfuran are reported. The bisTHF ligand with RR configuration at the amino groups and C8 alkyl chains (RR8) stabilized GC-rich duplex. In contrast, bisfuran compounds stabilized AT-rich duplex. The binding affinity of RR8 with 12 mer duplex DNA was determined by isothermal titration calorimetry to be 3.3 x 10(8) M-1.

  DOI：

  10.1081/ncn-100002331

文献信息

• Synthesis of [2,2’]Bifuranyl‐5,5’‐dicarboxylic Acid Esters <i>via</i> Reductive Homocoupling of <scp>5‐Bromofuran</scp> ‐2‐carboxylates Using Alcohols as Reductants ^†
  作者：Yi Xie、Bin Yu、Jiajun Luo、Biaolin Yin、Huanfeng Jiang

  DOI：10.1002/cjoc.202000303

  日期：2021.1

  alcohols to afford bifuranyl dicarboxylates. One of the final products in this protocol, [2,2’]bifuran‐5,5’‐dicarboxylic acid esters, are essential monomers of poly(ethylene bifuranoate), which can be served as an green and versatile alternative polymer for traditional poly(ethylene terephthalate) that is currently common in technical plastics.

  本文中，我们描述了一种环境友好且具有成本效益的方案，用于合成有价值的呋喃二甲酸二羧酸酯，首先是通过LiBr和K 2 S 2 O 8对易得的呋喃-2-羧酸酯进行α-溴化反应。此外，然后在醇存在下，在钯催化的还原均偶联反应中进行溴化中间产物5-溴呋喃-2-羧酸酯的合成，得到双呋喃基二羧酸酯。该协议的最终产品之一，[2,2'] bifuran-5,5'-二羧酸酯是聚（呋喃二甲酸乙二酯）的重要单体，可用作传统聚对苯二甲酸乙二醇酯的绿色多用途替代聚合物。 （对苯二甲酸乙二醇酯）目前在工业塑料中很常见。