(2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl)methanol | 1182723-37-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl)methanol
• 英文别名: [2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl]methanol
• CAS: 1182723-37-0
• 化学式: C₂₄H₁₈F₁₄O
• 分子量: 588.384
• InChiKey: MMEGATAFGJJGSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl)methanol 在 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 [2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl]methyl (2,5-dioxopyrrolidin-1-yl) carbonate
  参考文献：
  名称：

  Development of efficient processes for multi-gram scale and divergent preparation of fluorous-Fmoc reagents

  摘要：

  An optimized, multi-gram scale synthesis of fluorous-Fmoc reagents is described. Fmoc reagents bearing C3F7, C4F9, and C6F13 chains were prepared on multi-gram scale (ca. 1.0-7.0 g) in eight steps with overall yields of 73%, 60%, and 90%, respectively. The order of addition of the fluorous alkenes in a one-pot double tagging Heck reaction was also investigated in order to conduct an encoded mixture synthesis of f-Fmoc reagents. The target f-Fmoc reagents bearing C3F7, C4F9, and C6F13 chains could be effectively separated based on the fluorine content of the molecules. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.083
• 作为产物：
  描述：

  2,7-二硝基芴 在 sodium tetrahydroborate 、 tetrafluoroboric acid 、 palladium on activated charcoal 、 氢气 、 sodium hydride 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 反应 50.5h， 生成 (2,7-bis(3,3,4,4,5,5,5-heptafluoropentyl)-9H-fluoren-9-yl)methanol
  参考文献：
  名称：

  Development of efficient processes for multi-gram scale and divergent preparation of fluorous-Fmoc reagents

  摘要：

  An optimized, multi-gram scale synthesis of fluorous-Fmoc reagents is described. Fmoc reagents bearing C3F7, C4F9, and C6F13 chains were prepared on multi-gram scale (ca. 1.0-7.0 g) in eight steps with overall yields of 73%, 60%, and 90%, respectively. The order of addition of the fluorous alkenes in a one-pot double tagging Heck reaction was also investigated in order to conduct an encoded mixture synthesis of f-Fmoc reagents. The target f-Fmoc reagents bearing C3F7, C4F9, and C6F13 chains could be effectively separated based on the fluorine content of the molecules. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.083