1-phenyl-5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoroundecane | 6145-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-phenyl-5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoroundecane
• 英文别名: 1H,1H,2H,2H,3H,3H-perfluoroundecylbenzene；4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoroundecylbenzene
• CAS: 6145-10-4
• 化学式: C₁₇H₁₁F₁₇
• 分子量: 538.247
• InChiKey: VXQOUCIQYIJLFE-UHFFFAOYSA-N

物化性质

• 沸点：
  143 °C(Press: 11 Torr)
• 密度：
  1.479±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  1-phenyl-5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoroundecane 、 六羰基铬 以 四氢呋喃 、 二丁醚 为溶剂， 以92%的产率得到[(η6-C6H5((CH2)3(CF2)7CF3)2)Cr(CO)3]
  参考文献：
  名称：

  π Complexes of Fluorous Alkynes, Cyclobutadienes, and Benzenes:  Syntheses and Phase Properties of Cobalt and Chromium Tricarbonyl Adducts

  摘要：

  Reactions of Cr(CO)(6) and fluorous benzenes C6H6-x((CH2)(3)R-f8)(x) (x = a, 1; b, 2 (1,2); c, 2 (1,3); d, 2 (1,4); e, 3 (1,3,5); R-f8 = (CF2)(7)CF3; dibutyl ether, 140 degrees C) give the pi complexes (eta(6)-C6H6-x((CH2)(3)R-f8)Cr(CO)(3) (1a-e; 92-42%); p-R-f8(CH2)(3)C6H4CH(S(CH2)(3)Rf(8))(CH2)(2)R-f8 affords an analogous adduct (If; 47%). The CF3C6F11/toluene partition coefficients of 1a-f increase with the number of ponytails (three, 99:1 to 97:3; two, 91:9; one, 49:51); the fluorophilicities are only slightly less than a-f. The IR v(CO) values show any residual inductive effect of the perfluoroalkyl groups at chromium to be slight. The reaction of LiC equivalent to CSi(CH3)(3) and R-f8(CH2)(3)I gives the fluorous alkyne R-f8(CH2)(3)C CSi(CH3)(3) (2; 63%). Addition of wet n-Bu4N+ F- affords Rf(8)(CH2)(3)C equivalent to CH (71%), which upon treatment with t-BuLi and R-f8(CH2)(3)I yields R-f8(CH2)(3)C equivalent to C(CH2)(3)R-f8 (4; 58%). The reaction of 2 and CO2(CO)(8) gives the alkyne complex Co-2(CO)(6)(eta(2)-mu-R-f8(CH2)(3)CCSi(CH3)(3)) (88%). Reactions of 2 or 4 with (eta(5)-C5H5)CO(CO)(2) (2: 1, decane, 150-160 degrees C) give the pi cyclobutadiene complexes (eta(5)-C5H5)Co{eta(4)-C-4[Z](2)[(CH2)(3)R-f8](2)} (Z = Si(CH3)(3), 6, 70%; (CH2)(3)R-f8, 7, 32%). The CF3C6F11/toluene partition coefficients show 6 and 7 to be more fluorophilic than their precursors 2 and 4, despite the added (eta(5)-C5H5)CO groups.

  DOI：

  10.1021/om050950z
• 作为产物：
  描述：

  (4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundec-1-enyl)benzene 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 正己烷 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 24.0h， 以90%的产率得到1-phenyl-5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoroundecane
  参考文献：
  名称：

  荧光相固定的策略和设计：对马尾辫效果的系统研究？(CH2)3(CF2)n?1CF3对苯类化合物分配系数的影响

  摘要：

  氟溶剂通常表现出与有机溶剂的温度依赖性混溶性。因此，对含氟溶剂具有高亲和力的催化剂和试剂可用于结合单相化学（较高温度）和双相产物分离（较低温度）优点的方案。描述了苯甲醛（通过 Wittig 和氢化反应）向具有一到三个“马尾”（CH2）3（CF2）n-1CF3（n = 6、8、10）的烷基苯的高产率转化。甲苯-CF3C6F11 分配系数表明三个马尾辫是实现高度氟相固定所必需的。版权所有 © 2000 John Wiley & Sons, Ltd.

  DOI：

  10.1002/1099-1395(200010)13:10<596::aid-poc284>3.0.co;2-m

文献信息

• Stille Cross-Coupling of Activated Alkyltin Reagents under “Ligandless” Conditions
  作者：Agnes Herve、Alain L. Rodriguez、Eric Fouquet

  DOI：10.1021/jo047907q

  日期：2005.3.1

  Monoalkyltins activated by a fluoride source are shown to be as reactive as their vinyl or aryl homologues in the Stille coupling reaction, thus providing an easy entry into the pallado-catalyzed formation of Csp3−Csp2 bonds. In addition to this uncommon reactivity, this methodology holds several advantages such as (i) a quantitative preparation of stable and easy to handle alkyltin reagents 2, (ii) a simplified

  在Stille偶联反应中，由氟化物源活化的单烷基锡显示出与它们的乙烯基或芳基同系物一样的反应性，因此提供了容易进入Pallado催化的Csp 3 -Csp 2键的形成的能力。除了这种不常见的反应性之外，这种方法还具有一些优点，例如（i）定量制备稳定且易于处理的烷基锡试剂2，（ii）在中性条件下无需任何膦添加配体的简化偶联步骤，以及（iii）从无机无毒锡副产物中轻松纯化有机产物的步骤。
• 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。
• π Complexes of Fluorous Alkynes, Cyclobutadienes, and Benzenes:  Syntheses and Phase Properties of Cobalt and Chromium Tricarbonyl Adducts
  作者：Long V. Dinh、Crestina S. Consorti、Charlotte Emnet、J. A. Gladysz

  DOI：10.1021/om050950z

  日期：2006.2.1

  Reactions of Cr(CO)(6) and fluorous benzenes C6H6-x((CH2)(3)R-f8)(x) (x = a, 1; b, 2 (1,2); c, 2 (1,3); d, 2 (1,4); e, 3 (1,3,5); R-f8 = (CF2)(7)CF3; dibutyl ether, 140 degrees C) give the pi complexes (eta(6)-C6H6-x((CH2)(3)R-f8)Cr(CO)(3) (1a-e; 92-42%); p-R-f8(CH2)(3)C6H4CH(S(CH2)(3)Rf(8))(CH2)(2)R-f8 affords an analogous adduct (If; 47%). The CF3C6F11/toluene partition coefficients of 1a-f increase with the number of ponytails (three, 99:1 to 97:3; two, 91:9; one, 49:51); the fluorophilicities are only slightly less than a-f. The IR v(CO) values show any residual inductive effect of the perfluoroalkyl groups at chromium to be slight. The reaction of LiC equivalent to CSi(CH3)(3) and R-f8(CH2)(3)I gives the fluorous alkyne R-f8(CH2)(3)C CSi(CH3)(3) (2; 63%). Addition of wet n-Bu4N+ F- affords Rf(8)(CH2)(3)C equivalent to CH (71%), which upon treatment with t-BuLi and R-f8(CH2)(3)I yields R-f8(CH2)(3)C equivalent to C(CH2)(3)R-f8 (4; 58%). The reaction of 2 and CO2(CO)(8) gives the alkyne complex Co-2(CO)(6)(eta(2)-mu-R-f8(CH2)(3)CCSi(CH3)(3)) (88%). Reactions of 2 or 4 with (eta(5)-C5H5)CO(CO)(2) (2: 1, decane, 150-160 degrees C) give the pi cyclobutadiene complexes (eta(5)-C5H5)Coeta(4)-C-4[Z](2)[(CH2)(3)R-f8](2)} (Z = Si(CH3)(3), 6, 70%; (CH2)(3)R-f8, 7, 32%). The CF3C6F11/toluene partition coefficients show 6 and 7 to be more fluorophilic than their precursors 2 and 4, despite the added (eta(5)-C5H5)CO groups.
• Strategy and design in fluorous phase immobilization:�a systematic study of the effect of ?pony tails? (CH2)3(CF2)n?1CF3 on the partition coefficients of �benzenoid compounds
  作者：Christian Rocaboy、Drew Rutherford、Byron L. Bennett、J. A. Gladysz

  DOI：10.1002/1099-1395(200010)13:10<596::aid-poc284>3.0.co;2-m

  日期：2000.10

  Fluorous solvents commonly exhibit temperature-dependent miscibilities with organic solvents. Thus, catalysts and reagents that have high affinities for fluorous solvents can be used in protocols that combine the advantages of one-phase chemistry (higher temperature) and biphase product separation (lower temperature). The high-yield conversion of benzaldehydes (via Wittig and hydrogenation reactions)

  氟溶剂通常表现出与有机溶剂的温度依赖性混溶性。因此，对含氟溶剂具有高亲和力的催化剂和试剂可用于结合单相化学（较高温度）和双相产物分离（较低温度）优点的方案。描述了苯甲醛（通过 Wittig 和氢化反应）向具有一到三个“马尾”（CH2）3（CF2）n-1CF3（n = 6、8、10）的烷基苯的高产率转化。甲苯-CF3C6F11 分配系数表明三个马尾辫是实现高度氟相固定所必需的。版权所有 © 2000 John Wiley & Sons, Ltd.