5,5'-di(tert-butyl)-7,7'-diiodo-2,2'-biindolyl | 876124-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5,5'-di(tert-butyl)-7,7'-diiodo-2,2'-biindolyl
• 英文别名: 5,5'-di(tert-butyl)-7,7'-diiodo-2,2'-biindole；5-tert-butyl-2-(5-tert-butyl-7-iodo-1H-indol-2-yl)-7-iodo-1H-indole
• CAS: 876124-84-4
• 化学式: C₂₄H₂₆I₂N₂
• 分子量: 596.293
• InChiKey: NSFDFSXHWPKLOI-UHFFFAOYSA-N

物化性质

• 沸点：
  647.3±50.0 °C(Predicted)
• 密度：
  1.669±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,5'-di(tert-butyl)-7,7'-diiodo-2,2'-biindolyl 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ copper(l) iodide 、 potassium carbonate 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 18.33h， 生成 5,5'-di(tert-butyl)-7,7'-diethynyl-2,2'-biindole
  参考文献：
  名称：

  吲哚基大环化合物是阴离子的一类受体。

  摘要：

  DOI：

  10.1002/anie.200503121
• 作为产物：
  描述：

  4-tert-butyl-2-ethynyl-6-iodoaniline 在 吡啶 、 copper(l) iodide 、 copper diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 生成 5,5'-di(tert-butyl)-7,7'-diiodo-2,2'-biindolyl
  参考文献：
  名称：

  吲哚基大环化合物是阴离子的一类受体。

  摘要：

  DOI：

  10.1002/anie.200503121

文献信息

• Biindole-Bridged Porphyrin Dimer as Allosteric Molecular Tweezers
  作者：Chi-Hwa Lee、Hongsik Yoon、Woo-Dong Jang

  DOI：10.1002/chem.200901988

  日期：2009.10.5

  Allosteric molecular tweezers: By the introduction of porphyrin units to anion‐acceptable biindole moiety (see scheme), the binding affinity of Cl− was significantly enhanced owing to the π–π interaction of porphyrin units. Furthermore, the biindole‐bridged zinc porphyrin dimer binds Cl− as well as 1,4‐diazabicyclo[2.2.2]octane (DABCO) in a strong positive allosteric manner.

  变构分子镊子：通过引入卟啉单位阴离子可接受biindole部分（参见方案）的，氯的结合亲和力-由于卟啉单元的π-π相互作用显著增强。此外，biindole-桥接锌卟啉二聚体结合氯-以及一个强有力的正变构地1,4-二氮杂双环[2.2.2]辛烷（DABCO）。
• Biased Helical Folding of Chiral Oligoindole Foldamers
  作者：Veluru Ramesh Naidu、Min Cheol Kim、Jae-min Suk、Ho-Joong Kim、Myongsoo Lee、Eunji Sim、Kyu-Sung Jeong

  DOI：10.1021/ol8022243

  日期：2008.12.4

  Oligoindole-based chiral foldamers have been synthesized by incorporating (S)- or (R)-1-phenylethylamine to both ends of the tetraindole scaffold. The oligoindoles fold into a helical conformation upon binding an anion by hydrogen bonds, which gives rise to an induced circular dichroism (CD) signal of large amplitude, implying the preferential formation of one helical isomer over another. Theoretical calculations suggest that the (P)-helix of the (SS)-oligoindole 8a be more energetically stable than the corresponding (M)-helix.
• Biindolyl-based molecular clefts that bind anions by hydrogen-bonding interactions
  作者：Kyoung-Jin Chang、Min Kyung Chae、Changsoon Lee、Ji-Yeon Lee、Kyu-Sung Jeong

  DOI：10.1016/j.tetlet.2006.06.157

  日期：2006.9

  Molecular clefts were synthesized from 2,2'-biindolyl scaffold that contains good hydrogen bond donors of two indole NHs. The molecular clefts were systematically modified in two different manners to increase binding affinities toward chloride. The association constant dramatically increased when additional hydrogen-bonding sites of two benzamide units were incorporated to the biindolyl scaffold. For example, the association constants of 1a and 1b are 5.1 x 10(3) and 1.4 x 10(4) M-1 in CH3CN at 22 +/- 1 degrees C, while reference molecule 10 having only two indole NHs showed the association constant of 340 M-1 under the same conditions. When the biindolyl backbone was structurally preorganized, the binding affinities toward anions were further increased with additional stabilization energy (-Delta Delta G) of 2.0 +/- 0.2 kcal/mol). (c) 2006 Elsevier Ltd. All rights reserved.