1,4-双(3-碘丙基)苯 | 650604-04-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,4-双(3-碘丙基)苯
• 英文名称: 1,4-bis(3-iodopropyl)benzene
• 英文别名: 1,4-Bis(3-iodopropyl)benzene
• CAS: 650604-04-9
• 化学式: C₁₂H₁₆I₂
• 分子量: 414.068
• InChiKey: RMNFVLWZSYVWAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4-双(3-碘丙基)苯 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 生成 5,5'-(1,4-phenylene)bis[2-(methylthio)pentanal]
  参考文献：
  名称：

  Highly Regioselective Transformation of out/out-equatorial Bis(formylmethano)[60]fullerenes:  Construction of Dissymmetric [60]Fullerene-Centered Triads

  摘要：

  [GRAPHICS]Three kinds of out/out-equatorial bis( formylmethano)[ 60] fullerenes ( 1b-d) were obtained by the tether-directed bifunctionalization of [ 60] fullerene with bis( alpha-formylsulfonium ylide) s. The condensation of aromatic amines with 1b-d proceeded with an unexpectedly high regioselectivity to give one of two possible regioisomers of mono-imines as the main products ( the ratio of the regioisomers, up to 97: 3). By the transformation of the remaining formyl group in the mono-imines thus obtained, the corresponding dissymmetric bis-imines were efficiently synthesized.

  DOI：

  10.1021/jo060110+
• 作为产物：
  描述：

  [1,4-亚苯基]双(3-羟基丙烷) 在 氢碘酸 作用下， 反应 16.0h， 以76%的产率得到1,4-双(3-碘丙基)苯
  参考文献：
  名称：

  分子间和分子内 AD-Aπ-π 堆积的选择性形成：双（吡啶并丙基）苯的固态结构

  摘要：

  双(吡啶基丙基)苯衍生物[1,4-(4-R-C5H4N+CH2CH2CH2)2C6H4][X−]2的合成和分子结构(1, R = H, X = I; 2, R = tBu , X = Br) 进行了研究。化合物 1 在固态时采用线性结构，晶体堆积几何可以定义为由一个分子的亚苯基环和两个相邻分子的两个吡啶环形成的孤立的三联体。相比之下，化合物2呈S形排列，分子内受体-供体-受体三联体形成在同一分子的中心亚苯基环和两个末端吡啶环之间。1和2的晶体结构的这种明显差异可归因于吡啶鎓单元上的取代基。庞大的叔丁基的空间排斥阻碍了分子间 ADA π-π 堆积。

  DOI：

  10.1002/ejoc.200300310

文献信息

• Selective Formation of Inter- and Intramolecular A-D-Aπ-π Stacking: Solid-State Structures of Bis(pyridiniopropyl)benzenes
  作者：Take-aki Koizumi、Kanako Tsutsui、Koji Tanaka

  DOI：10.1002/ejoc.200300310

  日期：2003.12

  The synthesis and molecular structures of bis(pyridiniopropyl)benzene derivatives, [1,4-(4-R-C5H4N+CH2CH2CH2)2C6H4][X−]2 (1, R = H, X = I; 2, R = tBu, X = Br) have been investigated. Compound 1 adopts a linear structure in the solid state and the crystal packing geometry can be defined as isolated triplets formed by the phenylene ring of one molecule and two pyridinium rings of two neighboring molecules

  双(吡啶基丙基)苯衍生物[1,4-(4-R-C5H4N+CH2CH2CH2)2C6H4][X−]2的合成和分子结构(1, R = H, X = I; 2, R = tBu , X = Br) 进行了研究。化合物 1 在固态时采用线性结构，晶体堆积几何可以定义为由一个分子的亚苯基环和两个相邻分子的两个吡啶环形成的孤立的三联体。相比之下，化合物2呈S形排列，分子内受体-供体-受体三联体形成在同一分子的中心亚苯基环和两个末端吡啶环之间。1和2的晶体结构的这种明显差异可归因于吡啶鎓单元上的取代基。庞大的叔丁基的空间排斥阻碍了分子间 ADA π-π 堆积。
• Potent Antimalarial Activity of 2-Aminopyridinium Salts, Amidines, and Guanidines
  作者：Michèle Calas、Mahama Ouattara、Gilles Piquet、Zyta Ziora、Y. Bordat、Marie L. Ancelin、Roger Escale、Henri Vial

  DOI：10.1021/jm0704752

  日期：2007.12.13

  We describe the design, synthesis, and antimalarial activity of 60 bis-tertiary amine, bis-2(1H)-imino-heterocycle, bis-amidine, and bis-guanidine series. Bis-tertiary amines with a linker from 12 to 16 methylene groups were active against the in vitro growth of Plasmodium falciparum within the 10(-6)-10(-7) M concentration range. IC50 decreased by 2 orders of magnitude for bis-2-aminopyridinium salts, bis-amidines, and bis-guanidines (27 compounds with IC50 < 10 nM). Increasing the alkyl chain length from 6 to 12 methylene groups led to increased activity, while beyond this antimalarial activity decreased. Antimalarial activities appear to be strictly related to the basicity of the cationic head with an optimal pK(a) over 12.5. Maximal activity occurs for bis-2-aminopyridinium, two C-duplicated bis-amidines, and three bis-guanidines, with IC50 values lower than 1 nM. In. comparison to similar quaternary ammonium salts, amidinium compounds have distinct structural requirements for antimalarial activity and likely additional binding opportunities on account of their hydrogen-bond-forming properties.
• Highly Regioselective Transformation of <i>out</i>/<i>out</i>-<i>e</i><i>quatorial</i> Bis(formylmethano)[60]fullerenes:  Construction of Dissymmetric [60]Fullerene-Centered Triads
  作者：Hiroshi Ito、Yasuhiro Ishida、Kazuhiko Saigo

  DOI：10.1021/jo060110+

  日期：2006.6.1

  [GRAPHICS]Three kinds of out/out-equatorial bis( formylmethano)[ 60] fullerenes ( 1b-d) were obtained by the tether-directed bifunctionalization of [ 60] fullerene with bis( alpha-formylsulfonium ylide) s. The condensation of aromatic amines with 1b-d proceeded with an unexpectedly high regioselectivity to give one of two possible regioisomers of mono-imines as the main products ( the ratio of the regioisomers, up to 97: 3). By the transformation of the remaining formyl group in the mono-imines thus obtained, the corresponding dissymmetric bis-imines were efficiently synthesized.
• Regio- and diastereo-controlled synthesis of bis(formylmethano)[60]fullerenes and their application to the formation of [60]fullerene pearl-necklace polyimines
  作者：Hiroshi Ito、Yasuhiro Ishida、Kazuhiko Saigo

  DOI：10.1016/j.tetlet.2006.02.148

  日期：2006.5

  The tether-directed method was firstly applied to the biscyclopropanation of [60]fullerene via the addition-elimination reaction of bis(sulfonium ylide)s to give bis(formylmethano)[60]fullerenes with satisfactory regio- and stereoselectivity. The equatorialbisadduct thus obtained was used for the polycondensation with an aromatic diamine to afford the corresponding pearl-necklace polyimine with satisfactorily high degree of polymerization. (c) 2006 Elsevier Ltd. All rights reserved.