4-(3,8-Ditert-butyl-1-iodo-11,12-dihydroindolo[2,3-a]carbazol-10-yl)-2-methylbut-3-yn-2-ol | 1268691-72-0

• 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: 4-(3,8-Ditert-butyl-1-iodo-11,12-dihydroindolo[2,3-a]carbazol-10-yl)-2-methylbut-3-yn-2-ol
• CAS: 1268691-72-0
• 化学式: C₃₁H₃₃IN₂O
• 分子量: 576.52
• InChiKey: RAFOVXXATRKSSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  51.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(3,8-Ditert-butyl-1-iodo-11,12-dihydroindolo[2,3-a]carbazol-10-yl)-2-methylbut-3-yn-2-ol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成
  参考文献：
  名称：

  Folding-Generated Molecular Tubes Containing One-Dimensional Water Chains

  摘要：

  A series of indolocarbazole-pyridine (IP) oligomers were prepared that fold into helical conformations, and their folding features in solution and in the solid state were revealed. Helical folding of these IP foldamers is induced by dipolar interactions through the ethynyl bond and pi-stacking between two repeating units. Upon helical folding, H-1 NMR signals of aromatic protons were significantly shifted upfield by Delta delta = 0.5-2.2 ppm. In addition, hypochromic shifts and fluorescence quenching were observed in the absorption and emission spectra. X-ray crystal structures clearly demonstrated that IP foldamers folded to helical structures with cylindrical internal cavities wherein 3 or 5 water molecules were occupied by hydrogen-bonding interactions in a 1-D array, reminiscent of transmembrane water channels, called aquaporins.

  DOI：

  10.1021/jacs.5b11808
• 作为产物：
  描述：

  3,8-Di-tert-butyl-1,10-diiodo-11,12-dihydro-11,12-diaza-indeno[2,1-a]fluorene 、 2-甲基-3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到4-(3,8-Ditert-butyl-1-iodo-11,12-dihydroindolo[2,3-a]carbazol-10-yl)-2-methylbut-3-yn-2-ol
  参考文献：
  名称：

  吲哚并咔唑三聚体具有扩大的阴离子结合腔。

  摘要：

  由阴离子丁二酰基单元连接的三个吲哚并咔唑组成的吲哚并咔唑三聚体已被制备为阴离子受体（见图）。该三聚体在通过多个氢键与阴离子结合后折叠成螺旋构象。与具有较短乙炔基接头的类似物相比，该受体与大阴离子（如磷酸二氢盐和乙酸盐）的亲和力大大提高。

  DOI：

  10.1002/asia.201100087

文献信息

• Selective sulfate binding induces helical folding of an indolocarbazole oligomer in solution and solid state
  作者：Jun-il Kim、Hemraj Juwarker、Xinfang Liu、Myoung Soo Lah、Kyu-Sung Jeong

  DOI：10.1039/b919519j

  日期：——

  Hydrogen bonding to anions drives the helical folding of an indolocarbazole oligomer, thus resulting in an internal cavity with six NHs and two OHs for binding sulfate with high selectivity.

  氢与阴离子的键合驱动吲哚并咔唑低聚物的螺旋折叠，从而形成一个内腔，其中有六个NH和两个OH以高选择性结合硫酸盐。
• Aromatic Hybrid Foldamer with a Hydrophilic Helical Cavity Capable of Encapsulating Glucose
  作者：Ji Young Hwang、Hae-Geun Jeon、Ye Rin Choi、Junyoung Kim、Philjae Kang、Seungwon Lee、Kyu-Sung Jeong

  DOI：10.1021/acs.orglett.7b02768

  日期：2017.10.20

  An indolocarbazole–naphthyridine hybrid oligomer capable of adopting a stable helical conformation was prepared, and its folding properties were thoroughly studied in the solid state and in solution. As a result of folding, a hydrophilic cavity was generated inside the helix wherein monosaccharides were able to be encapsulated in the order of glucose (9.6 × 104 M–1) > galactose (1.0 × 104 M–1) ≫ mannose

  制备了能够采用稳定的螺旋构象的吲哚并咔唑-萘啶杂化低聚物，并在固态和溶液中对其折叠性能进行了深入研究。折叠的结果是，在螺旋内部产生了一个亲水腔，单糖能够按照葡萄糖（9.6×10 4 M –1）>半乳糖（1.0×10 4 M –1）≫甘露糖（〜 0）在10％（v / v）DMSO / CH 2 Cl 2中。
• Foldamer-based helicate displaying reversible switching between two distinct conformers
  作者：Hae-Geun Jeon、Hyun Kyung Lee、Seungwon Lee、Kyu-Sung Jeong

  DOI：10.1039/c8cc02758g

  日期：——

  A new double-stranded dinuclear helicate that displays conformational switching in response to temperature was prepared by self-assembly of an aromatic helical foldamer and dichloropalladium(II). The relative populations of the two helicate conformers, syn–anti and syn–syn, were demonstrated to be reversibly modulated through temperature control.

  通过芳族螺旋折叠剂和二氯钯（II）的自组装制备了一种新的显示响应温度的构象转换的双链双核螺旋体。已证明通过温度控制可逆地调节了两个螺旋构象异构体syn - anti和syn - syn的相对种群。