2-Iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate | 83310-90-1

• 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: 2-Iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate
• 英文别名: 1-Acetoxy-2-iodo-3-perfluorohexylpropane；3-(F-hexyl)-2-iodopropyl acetate；Acetic acid=4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononyl ester；(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-iodononyl) acetate
• CAS: 83310-90-1
• 化学式: C₁₁H₈F₁₃IO₂
• 分子量: 546.067
• InChiKey: NYJOEEQEXZLXAN-UHFFFAOYSA-N

物化性质

• 沸点：
  62 °C(Press: 0.05 Torr)
• 密度：
  1.796±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  2-Iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate 在 锌 作用下， 以 二乙二醇 为溶剂， 126.0 ℃ 、15.07 kPa 条件下， 以88%的产率得到3-(perfluorohexyl)prop-1-ene
  参考文献：
  名称：

  Effect of a perfluoroalkyl group on the elimination and substitution reactions of two homologous series of perfluoroalkyl-substituted iodoalkanes

  摘要：

  DOI：

  10.1021/jo00187a012
• 作为产物：
  描述：

  乙酸烯丙酯 、 全氟己基碘烷 在 过氧化苯甲酰 作用下， 以95%的产率得到2-Iodo-4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl acetate
  参考文献：
  名称：

  新型氟化吗啉代丙烯酸酯和甲基丙烯酸酯的合成与聚合

  摘要：

  分四个步骤以非常高的产率合成了在侧链上带有吗啉代基团的四种氟化丙烯酸酯和甲基丙烯酸酯：将全氟烷基碘自由基自由基加到乙酸烯丙酯上，然后进行碱性环化，得到氟化环氧化物。这些化合物与过量的吗啉反应，生成吗啉代氟化的醇，它们与丙烯酸或甲基丙烯酸酐缩合，分别生成预期的氟化丙烯酸或甲基丙烯酸单体。这种新烯烃的均聚行为涉及对传播速率常数与终止速率常数之比的平方的研究（）通过两种不同的方法。GC动力学研究和收率计算表明，这些单体的反应性较差。值表明，它们的反应性比普通的氟化丙烯酸单体低两倍。我们最终提出了此类氟化单体的反应规模。

  DOI：

  10.1016/0022-1139(95)03281-h

文献信息

• Rearrangement of 2-iodo-3-perfluoroalkyl-1-propyl acetates to 1-iodo-3-perfluoroalkyl-2-propyl acetates
  作者：M. Kotora、M. Hájek、J. Kvíčala、B. Ameduri、B. Boutevin

  DOI：10.1016/s0022-1139(00)80559-x

  日期：1993.10

  2-Iodo-3-perfluoroalkylpropyl acetates, RFCH2CHICH2OAc (1) (RF = i-C3F7, C4F9, C6F13, C8F17), have been rearranged thermally to 1-iodo-3-perfluoroalkyl-2-propyl acetates, RFCH2CH(OAc)CH2I (2), in 89% yield over the temperature range 120–200 °C. The results indicate that the rearrangement is a reversible process which is shifted towards the formation of 2. The equilibrium regio isomer ratio (12 = 1:8)

  乙酸2-碘-3-全氟烷基丙基酯R F CH 2 CHICH 2 OAc（1）（R F = iC 3 F 7，C 4 F 9，C 6 F 13，C 8 F 17）已热重排为1 -碘-3-全氟烷基-2-丙基乙酸酯，R F CH 2 CH（OAc）CH 2 I（2），在120–200°C的温度范围内，产率为89％。结果表明，重排是一个可逆的过程，向2的形成转移。。平衡区域异构体比率（12 = 1：8）与温度和R F取代基的性质无关。提出重排通过自由基机理进行，所述自由基机理包括在C 1 I键热断裂后乙酰氧基的1，2-迁移。
• Radical-induced reaction of monoiodo- and diiodo-perfluoroalkanes with allyl acetate: telomer and rearranged products, mass-spectral distinguishing of regioisomers
  作者：V. Církva、B. Améduri、B. Boutevin、J. Kvíčala、O. Paleta

  DOI：10.1016/0022-1139(95)03242-6

  日期：1995.9

  (2a-c)] and 2:1 telomers (5a-c) underwent subsequent thermal rearrangement [formation of RFCH2CH(OCOCH3)CH2I, (3a-c), and telomers (6a-c), respectively] at elevated temperatures. In the reaction of diiodides IQI, monoadducts [CH3COOCH2CHICH2QI, (9a,b)] and diadducts [(CH3COOCH2CHICH2)2Q (10a,b)] were formed, but no telomeric and rearranged products were found under the reaction conditions employed. On the

  过氧化引发剂引发的单碘全氟烷烃R F I（R F = C 4 F 9，C 6 F 13，C 8 F 17）和二碘全氟烷烃IQI（Q = C 4 F 8，C 6 F 12）与乙酸烯丙酯的自由基反应描述。在所采用的反应条件下，大多数情况下，R F I和IQI的转化均完成。R F的反应我还产生了一些2：1端粒，它们是已表征的新化合物。在某些情况下，以高达34％的制备产率分离端粒。1：1的加合物[R F CH 2 CHICH 2 OCOCH 3，（2a-c） ]和2：1的端粒（5a-c）都进行了后续的热重排[R F CH 2 CH（OCOCH 3）CH 2 I的形成，（3a-c）和端粒（6a-c） ]。在二碘化物IQI的反应中，单加合物[CH 3 COOCH 2 CHICH 2 QI，形成（9a，b） ]和二加合物[（CH 3 COOCH 2 CHICH 2）2 Q（10a，b）]，但在所采用的反
• Some approaches to the synthesis of fluorinated alcohols and esters. II. Use of F-alkyl iodides for the synthesis of F-alkyl alkanols
  作者：Neal O. Brace

  DOI：10.1016/s0022-1139(00)82223-x

  日期：1982.5

  catalyst (strong base acid acceptor), can be done either in one step or via RFCHCHCH2OH; however, dehydrohalogenation may also give the epoxide, and reduction in this case leads to the secondary alcohol, RFCH2CH(CH3)OH. By contrast, reduction of RFCH2CHICH2OAc by tributyltin hydride or with hydrogen over palladium (diethylamine acid acceptor) goes smoothly. Zinc and acid reduction of RFCH2CHICH2OAc gives

  自由基加成的F-烷基碘（R的˚F I）中的烯醇或酯，接着进行适当的还原是用于制备同系物的相应F-烷基-链烷醇的有效方法，R ˚F（CH 2）ñ -哦。当n = 2.4或更高时，这两个步骤会顺利进行。然而，1,2,3-取代的体系R F CH 2 CHYCH 2 Z易受意料之外的困难的影响。的R还原˚F CH 2 CHICH 2 ON至R ˚F（CH 2）3 OH由氢和催化剂（强碱酸受体），既可以在一个步骤中或经由R个进行˚F CHCHCH 2 OH; 但是，脱卤化氢也可能产生环氧化物，在这种情况下的还原反应会生成仲醇R F CH 2 CH（CH 3）OH。相比之下，通过氢化三丁基锡或在钯（二乙胺酸受体）上用氢还原R F CH 2 CHICH 2 OAc可以顺利进行。锌和酸压下量R的˚F CH 2 CHICH 2 OAC给出消除至R ˚F CH 2 CHCH 2 ; 甚至ř ˚F CHCICH
• Highly selective synthesis of [(perfluoroalkyl) methyl] oxiranes (by the addition of iodoperfluoroalkanes to allyl acetate)
  作者：Vladimír Církva、Bruno Améduri、Bernard Boutevin、Oldřich Paleta

  DOI：10.1016/s0022-1139(97)00018-3

  日期：1997.7

  Mixtures of regioisomeric adducts of monoiodoperfluoroalkanes R-F-I (R-F = C4F9, C6F13 C8F17) with allyl acetate, RFCH2CHICH2OAc (1a-1c) and rearranged adducts RFCH2CH(OAc)-CH2I (2a-2c), were converted chemoselectively to the corresponding oxiranes RFCH2CH(-O-)CH2 (3a-3c) in yields of 94-96% (total yields of the two-step synthesis starting from R-F-I were 85-87%). The chemoselectivity of the oxirane formation appeared to be very dependent on the solvent used. Dependence on the reaction conditions on formation of byproducts RFCH=CHCH2OAc (4a-4c) and RFCH=CHCH2OH (5a-5c) in the epoxidation reaction was studied. (C) 1997 Elsevier Science S.A.
• Novel perfluoroalkylated derivatives of d-galactopyranose and xylitol for biomedical uses. Hemocompatibility and effect on perfluorocarbon emulsions
  作者：Vladimı́r Cı́rkva、Radek Polák、Oldřich Paleta、Karel Kefurt、Jitka Moravcová、Milan Kodı́ček、Stanislav Forman

  DOI：10.1016/j.carres.2004.06.019

  日期：2004.9

  6-O-(4,4,5,5,6,6,7,7,7-Nonafluoro-2-hydroxyheptyl)-, 6-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, and 6-O-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl)-D-galactopyranose (9, 10, and 11, resp.) were prepared by a two-step synthesis including the reaction of 1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose with 2-[(perfluoroalkyl)methyl]oxiranes under catalysis with BF3.Et2O. Similarly, 1-O-(4,4,5,5,6,6,7,7,7-nonafluoro-2-hydroxyheptyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-2-hydroxynonyl)-, 1-O-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-2-hydroxyundecyl)-DL-xylitol (18, 19, and 20, resp.) were prepared by a two-step synthesis from the corresponding 1,2:3,4-di-O-isopropylidene-DL-xylitol. Most of the both types of fluoroalkylated carbohydrate derivatives 9-11 and 18-20 generally displayed very low level of hemolytic activity and excellent co-emulsifying properties on testing on perfluorodecalin-Pluronic F-68 microemulsions. (C) 2004 Elsevier Ltd. All rights reserved.