1,10-diiodo-3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorodecane | 1813-83-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机碘化物
• 英文名称: 1,10-diiodo-3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorodecane
• 英文别名: 3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-1,10-diiododecane；1,10-diiodo-1H,1H,2H,2H,9H,9H,10H,10H-perfluorodecane；3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-1,10-diiodo-decane；3,3,4,4,5,5,6,6,7,7,8,8-Dodecafluor-1,10-diiod-decan；Decane, 3,3,4,4,5,5,6,6,7,7,8,8-dodecafluoro-1,10-diiodo-
• CAS: 1813-83-8
• 化学式: C₁₀H₈F₁₂I₂
• 分子量: 609.963
• InChiKey: FPHLHLVYLCQBKG-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C
• 沸点：
  301.7±10.0 °C(Predicted)
• 密度：
  2.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1,10-diiodo-3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorodecane 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 四氢呋喃 、 水 、 二甲基亚砜 为溶剂， 反应 54.0h， 生成 4,4,5,5,6,6,7,7,8,8,9,9-Dodecafluoro-undecanenitrile
  参考文献：
  名称：

  Synthesis and preliminary assessments of hybrid hydrocarbon–fluorocarbon anionic and non-ionic surfactants

  摘要：

  We describe the synthesis and preliminary physico-chemical assessments of ionic and non-ionic hybrid hydrofluorocarbon amphiphiles. Monoreduction reaction of the symmetrical starting material 1,10-diiodo-3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorodecane provides the ethyl terminated fluorocarbon chains. These non-symmetrical hydrofluorocarbon surfactants contain an ethyl segment, a fluorocarbon core and either nonionic or anionic polar heads (sulfate. sulfonate, phosphate. carboxylate or glycosidic groups). The lactobionolactone can be reacted with hydrofluorocarbon amines to obtain the non-ionic hydrophilic moiety whereas the anionic heads come from monoiodo and/or hydroxyl hydrofluorocarbon substrates. The critical micellar concentration (CMC) values of these novel surfactants were determined by surface tension and conductivity measurements. The results are compared to those measured with fluorinated homologues previously described. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00506-8
• 作为产物：
  描述：

  乙烯 、 1,6-二碘代十二氟己烷 生成 1,10-diiodo-3,3,4,4,5,5,6,6,7,7,8,8-dodecafluorodecane
  参考文献：
  名称：

  氟化双官能单体的合成

  摘要：

  为了获得用于氟聚氨酯的氟化双官能单体，我们从相应的二醇[HOCH 2 CH 2（CF 2）n CH 2 CH 2 OH]合成了新型氟化脂肪族二异氰酸酯[OCNCH 2（CF c2）n CH 2 NCO ]。用三氧化铬-硫酸将二醇氧化，得到高产率的α，α，ω，ω-四氢全氟亚烷基二羧酸。然后用五氯化磷处理酸，得到相应的二羧基氯化物，其易于与肼酸-吡啶配合物转化为二羧基叠氮化物。最后，在叠氮化物的库尔修斯重排上，从起始二醇得到的终产物α，α，ω，ω-四氢全氟亚烷基二异氰酸酯的产率为53％（n = 4）和19％（n = 6）。

  DOI：

  10.1016/s0022-1139(00)81542-0

文献信息

• Crosslinking of fluoroelastomers by “click” azide-nitrile cycloaddition
  作者：Guillaume Tillet、Gérald Lopez、Ming-Hong Hung、Bruno Améduri

  DOI：10.1002/pola.27549

  日期：2015.5.15

  A fluoroelastomer that bears pendant nitrile groups is crosslinked with a telechelic bis‐azido fluorinated curing agent by “click” azide–nitrile cycloaddition. Thermogravimetric analyses of the resulting press cured films reveal an improvement by 20 °C of the thermal degradation profile under air, compared to that of the corresponding uncured fluoroelastomer.

  带有悬垂腈基的含氟弹性体通过“点击”叠氮化物-腈环加成反应与远螯双叠氮基氟化固化剂交联。与相应的未固化的含氟弹性体相比，所得压制固化的膜的热重分析显示在空气中的热降解曲线提高了20°C。
• Copper catalyzed grignard cross-coupling reaction with β-perfluoroalkyl-substituted alkyl halides
  作者：Rie Shimizu、Eiichi Yoneda、Takamasa Fuchikami

  DOI：10.1016/0040-4039(96)01155-0

  日期：1996.7

  Coupling reaction of β-perfluoroalkyl-substituted alkyl halides with Grignard reagents such as phenyl-, vinyl-, allyl-, benzyl-, and alkyl-magnesium halides was catalyzed by copper salts or complexes to give the corresponding cross-coupling products in good yields. α,ω-Diiodoalkane bearing a polyfluoroalkylene moiety also reacted with 2 equiv. of Grignard reagent in the presence of copper catalyst

  铜盐或配合物催化β-全氟烷基取代的烷基卤化物与格氏试剂如苯基卤，乙烯基卤，烯丙基卤，苄基卤和烷基镁卤的偶合反应，从而以高收率得到相应的交叉偶合产物。带有多氟亚烷基部分的α，ω-二碘链烷也与2当量反应。铜催化剂存在下，用格氏试剂制备α，ω-双官能化产物。
• Fluorine-containing .alpha.,.beta.-bifunctional compounds and process
  申请人：Sagami Chemical Research Center

  公开号：US05151535A1

  公开（公告）日：1992-09-29

  A fluorine-containing .alpha.,.omega.-bifunctional compound having the formula: ##STR1## wherein each of R.sup.1 and R.sup.2 independently is a hydrogen atom, an alkyl group or an aralkyl group; X is --COOH, --COOR.sup.3, --COY or --NCO, wherein R.sup.3 is an alkyl group or an aralkyl group and Y is a halogen atom or N.sub.3 ; and n is an integer of at least 1 provided that when X is --COOH, n is an integer of at least 4.

  一种含氟的α，ω-双官能团化合物，其化学式为：##STR1##其中R.sup.1和R.sup.2中的每一个独立地是氢原子、烷基团或芳基烷基团；X为--COOH、--COOR.sup.3、--COY或--NCO，其中R.sup.3为烷基团或芳基烷基团，Y为卤素原子或N.sub.3；n为至少为1的整数，但当X为--COOH时，n为至少为4的整数。
• Synthesis of telechelic dienes from fluorinated α,ω-diiodoalkanes. Part I. Divinyl and diallyl derivatives from model I(C2F4)nI compounds
  作者：A. Manseri、B. Améduri、B. Boutevin、M. Kotora、M. Hajek、G. Caporiccio

  DOI：10.1016/0022-1139(95)03231-2

  日期：1995.8

  The synthesis of five fluorinated non-conjugated dienes from commercially available α,ω-diiodoperfluoroalkanes is described. Preparation of the fluorinated divinyl derivatives H2C=CH(CF2)nCH=CH2 (n = 2, 4, 6) (2,2, 2,4 and 2,6) was effected by ethylenation of these diiodinated compounds in various ways followed by dehydroiodination in ethanolic potassium hydroxide. Allyl diolefines, H2C=CHCH2(CF2)nCH2CH=CH2

  描述了由市售的α，ω-二碘全氟烷烃合成五个氟化的非共轭二烯。氟化二乙烯基衍生物的制备H 2 C = CH（CF 2）Ñ CH = CH 2（Ñ = 2，4,6）（2,2，2,4-和2,6-）通过这些二碘化化合物的ethylenation实现以各种方式，然后在乙醇氢氧化钾中进行加氢碘化。烯丙基二烯烃，H 2 C = CHCH 2（CF 2）n CH 2 CH = CH 2（4,4和4,6）是通过乙酸烯丙酯的α，ω-双端聚反应，然后在锌的存在下进行脱碘乙酰乙酸化而产生的。由于最终通过β-断裂分解α，ω-二碘全氟乙烷，因此获得了各自的二烯丙基4,4和4,6的二乙酸酯前体3,4和3,6，而不是二乙酸酯3,2。这五个氟化的非共轭二烯已通过1 H，13 C和19 F NMR光谱进行了表征。
• Synthesis of fluorine-containing nitro compounds
  作者：A.A. Malik、T.G. Archibald、D. Tzeng、L.C. Garver、K. Baum

  DOI：10.1016/s0022-1139(00)82947-4

  日期：1989.5

  were synthesized from 1-iodo-1H,1H,2H-perfluoroalkanes by displacing the iodide with sodium nitrite and then oxidatively nitrating the 1-nitro-1H,1H,2H,2H-perfluoroalkanes with tetranitromethane. Reaction with formaldehyde gave the dinitroalcohols, 6a and 6b. α,ω-Diiodo-perfluoroalkanes (1c and 1d) were similarly converted to tetranitrofluoroalkanes (5c and 5d), characterized as tetranitrodiols, 6c

  通过用亚硝酸钠置换碘化物，然后氧化硝化1的碘化物，由1-碘-1H，1H，2H-全氟烷烃合成具有结构-CF 2 CH 2 CH（NO 2）2的氟硝基烷烃（5a和5b）。-硝基-1H，1H，2H，2H-全氟烷烃与四硝基甲烷 与甲醛反应得到二硝基醇6a和6b。α，ω-二碘全氟烷烃（1c和1d）类似地转化为四硝基氟烷烃（5c和5d），其特征为四硝基二醇6c和6d，以及迈克尔与丙烯酸甲酯的加成物7c和7d。