4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)phenol | 522609-22-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)phenol
• CAS: 522609-22-9
• 化学式: C₁₇H₁₁F₁₇O
• 分子量: 554.247
• InChiKey: PSBAXECRYHICMC-UHFFFAOYSA-N

物化性质

• 沸点：
  322.8±42.0 °C(Predicted)
• 密度：
  1.530±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.72
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)phenol 在 溴 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2-bromo-4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-1-isopropoxybenzene
  参考文献：
  名称：

  Synthesis, Reaction, and Recycle of Light Fluorous Grubbs−Hoveyda Catalysts for Alkene Metathesis

  摘要：

  Light fluorous versions of first- and second-generation Grubbs-Hoveyda metathesis catalysts are introduced. These exhibit the expected reactivity profile, are readily recovered from reaction mixtures by fluorous solid-phase extraction, and can be routinely reused five or more times. The catalysts can be used in a stand alone fashion, or supported on fluorous silica gel.

  DOI：

  10.1021/jo048001n
• 作为产物：
  描述：

  1-Benzyloxy-4-((E)-4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undec-1-enyl)-benzene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 以91%的产率得到4-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)phenol
  参考文献：
  名称：

  Convenient syntheses of fluorous phenols of the formula HOC6H5−n((CH2)3(CF2)7CF3)n (n=1, 2) and the corresponding triarylphosphites

  摘要：

  The aldehydic benzyl ethers PhCH2OC6H4CHO (2; a/b = para/meta series) are readily available from the corresponding phenols and react with Wittig reagents derived from LPh3PCH2CH2Rf8]I-+(-) (R-f8 = (CF2)(7)CF3) to give PhCH2OC6H4CH=CHCH2Rf8 (86-93%, Z major). Reactions with H-2 over Pd/C give the fluorous phenols HOC6H4(CH2)(3)R-f8 (4a,b; 87-91%). Condensations with PCl3 and NEt3 (3.0:1.0:3.3 mol ratio) give the fluorous phosphites P[OC6H4(CH2)(3)R-f8](3) (5a,b; 92-94%), but traces of 4a,b are difficult to remove. The phthalate-based benzyl ethers PhCH2OC6H3 (COOR)(2) (7; c/d = 3,5/3,4 -OC6H3-3,n-(R)(2) series) are easily accessed and reduced with LiAlH4 to the diols PhCH2OC6H3(CH2OH)(2) (8c,d; 89-90%). Diol 8c and the Dess-Martin periodinane react to give the dialdehyde PhCH2OC6H3(CHO)(2) (9C; 95%). This is elaborated by a sequence analogous to 2 --> 4 --> 5 to the fluorous phenol HOC6H3((CH2)(3)R-f8)(2) (11C; 97%/96%, two steps) and phosphite P[OC6H3((CH2)(3)R-f8)(2)](3) (12c, 92%), from which traces of 11c are difficult to remove. Diol 8d can be similarly elaborated to 11d, but the dialdehyde 9d is labile and the combined yield of the Dess-Martin[Wittig steps is 32%. The CF3C6F11/toluene partition coefficients of 11c,d, and 12c (two pony tails; 70:30, 72:28, 92:8) are much higher than those of 4a and b (one pony tail; 12:88, 14:86). (C) 2002 Elsevier Science B.V.. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00242-7