6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heptadecafluoro-tridecanal | 172916-11-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heptadecafluoro-tridecanal
• 英文别名: 6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heptadecafluorotridecanal
• CAS: 172916-11-9
• 化学式: C₁₃H₉F₁₇O
• 分子量: 504.187
• InChiKey: MURQUJINLCNFFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heptadecafluoro-tridecanal 在 palladium on activated charcoal 氢气 、 三乙酰氧基硼氢化钠 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， 反应 5.0h， 生成 6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heptadecafluoro-tridecylamine
  参考文献：
  名称：

  方便合成一系列易于回收的含氟伯、仲和叔脂肪族胺 NH3−x[(CH2)m(CF2)7CF3]x(m = 3−5;x = 1−3) − 微调碱度和氟相亲和力

  摘要：

  醇 HOCH2(CH2)m−1(CF2)7CF3 [m = 3−5; (CF2)7CF3 = Rf8] 被氧化成醛 O=CH(CH2)m-1Rf8（Dess-Martin 试剂，90-96%），与 NH2CH2C6H5 和 Na(AcO)3BH 缩合得到苄胺 NH(CH2C6H5) [(CH2)mRf8]（过量的胺，88-90%）或 N(CH2C6H5)[(CH2)mRf8]2（过量的醛，85-91%）。随后的氢解 (Pd/C, 1 atm H2) 得到标题伯胺 NH2[(CH2)mRf8] (10-12; 98-99%) 或仲胺 NH[(CH2)mRf8]2 (13-15; 92) −99%）。醛缩合与 13-15 重复，得到叔胺 N[(CH2)mRf8]3 (16-18；86-97%)，具有非常高的氟相亲和力。随着 CH2 基团数量的增加或 Rf8 基团的减少，这些单调减少（CF3C6F11/甲苯，24

  DOI：

  10.1002/1099-0690(200007)2000:14<2621::aid-ejoc2621>3.0.co;2-h
• 作为产物：
  描述：

  全氟辛基碘烷 在 盐酸 、 锌 作用下， 生成 6,6,7,7,8,8,9,9,10,10,11,11,12,12,13,13,13-Heptadecafluoro-tridecanal
  参考文献：
  名称：

  Hetero Diels-Alder cyclocondensation of F-alkyl aldehydes with the Danishefsky diene

  摘要：

  The heterocyclocondensation of F-alkylated aldehydes R-F(CH2)(n)CHO with Danishefsky's diene depends on the mutual vicinity of the carbonyl and the F-alkyl chain: when n = 4 it leads to 4-oxo pyr-2-ene 4, but when n = 0 the trimethylsilyloxypyrene 3 without methoxy elimination only results. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01366-x

文献信息

• Synthesis of Per(poly)fluoroalkyl aldehydes RF(CH2)nCHO
  作者：Laurence Le´veˆque、Maurice Le Blanc、Raphae¨l Pastor

  DOI：10.1016/s0040-4039(98)02029-2

  日期：1998.11

  We report the preparation of polyfluoroalkyl aldehydes RF(CH2)nCHO in high yields by direct oxidation of polyfluoroalkyl alcohols; the Swern oxidation, pyridinium chlorochromate and Dess-Martin periodinane are used and compared

  我们报道了通过直接氧化多氟烷基醇来制备高产率的多氟烷基醛R F（CH 2）n CHO；比较了Swern氧化法，氯铬酸吡啶鎓盐和Dess-Martin高碘烷
• New anionic glycophospholipids with two perfluorocarbon or two hydrocarbon or mixed hydrophobic chains
  作者：Frédéric Guillod、Jacques Greiner、Jean G. Riess

  DOI：10.1016/0009-3084(95)02492-2

  日期：1995.11

  Novel amphiphilic anionic sugar phosphates esterified by various hydrophobic double-chain tails were synthesized. They differ primarily by the design of their hydrophobic tail. Amphiphile 12a derives from phosphogalactose and has two perfluoroalkylated hydrophobic chains; 12b has a pentenyloxy spacer between the mixed hydrocarbon/fludrocarbon double-chain and the same head group; 12c and 14c are galactose and glucose derivatives with two hydrocarbon tail chains. All were prepared through a three-step H-phosphonate route: reaction of the hydrophobic double-chain alcohol on phosphorus trichloride (27-60%), followed by the addition of the appropriately protected sugar, by oxidation (50-81%), and finally by deprotection of the sugar (58-95%). The starting alcohols were prepared through conventional reactions. Their synthesis was however, difficult, essentially as a result of lesser reactivity, and of low solubility of some of the intermediates related to the presence of the bulky, strongly hydrophobic chains. Preliminary biocompatibility assays indicate a reduction in hemolytic activity by increasing the number of fluorinated chains or by increasing the total length, hence the hydrophobicity of the amphiphile. Acute toxicity tests indicate maximum intravenously tolerated doses in mice of ca. 500 mg/kg body weight for 12a and 12b.
• Asymmetric heterocyclocondensation of polyfluorinated aldehydes catalysed by a chiral titanium(IV) complex
  作者：Laurence Lévêque、Maurice Le Blanc、Raphaël Pastor

  DOI：10.1016/s0040-4039(00)00762-0

  日期：2000.6

  The Binol/Ti(OiPr)(4) chiral titanium complex catalyses the asymmetric cyclocondensation of polyfluoroalkylaldehydes with the Danishefsky's diene leading to chiral polyfluoroalkyl dihydropyrenones with high enantiomeric excesses. (C) 2000 Published by Elsevier Science Ltd.
• A convenient access to (F-alkyl)alkanals
  作者：Gianluca Pozzi、Silvio Quici、Ian Shepperson

  DOI：10.1016/s0040-4039(02)01290-x

  日期：2002.8

  Aldehydes R-F(CH2)(m)CHO (R-F=n-CnF2n+1) have been prepared in good yields by oxidation of the corresponding alcohols using inexpensive and safe oxidants such as phenyliodine (III) diacetate and trichloroisocyanuric acid in the presence of 2,2.6,6-tetramethyl-1-piperidinyloxyl free-radical (TEMPO) as a catalyst. (C) 2002 Elsevier Science Ltd. All rights reserved.