anti-7-trifluoroacetoxynadic anhydride | 1428307-29-2

• 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: anti-7-trifluoroacetoxynadic anhydride
• CAS: 1428307-29-2
• 化学式: C₁₁H₇F₃O₅
• 分子量: 276.169
• InChiKey: QNKBYHLWKPKBNM-OUXNELDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.59
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  anti-7-hydroxynadic acid 、 三氟乙酸酐 反应 72.0h， 以89%的产率得到anti-7-trifluoroacetoxynadic anhydride
  参考文献：
  名称：

  The synthesis of fluorinated endcaps: Part 2. Preserving the endo,endo configuration in the monohydrolysis of 7-fluorinated nadic diesters

  摘要：

  Fluorination should impart greater thermal-oxidative stability to the versatile norbonenyl system. Anti-7-Fluoronadic and 7,7-difluoro nadic acid esters (5-norbornenyl-2-endo,3-endo-acid esters) 5c and 5d were synthesized as precursors for a variety of uses including the manufacture of high temperature aerospace polyimides (7c and 7d). Acid ester 5c and 5d cannot be simply prepared by the saponification of symmetrical diesters 3c and 3d because of concomitant epimerization. We have developed an alternative approach, involving the preparation and monohydrolysis of the mixed t-butyl methyl diesters 8c and 8d - while maintaining the cis-endo,endo configuration around the C-2 and C-3 linkage. Selective ester hydrolysis of the mixed esters mediated by formic acid produced the desired acid ester 5c and 5d. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.01.030