2-oxo-2-([2.2]paracyclophane-4-yl)ethanoyl chloride | 108869-36-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-oxo-2-([2.2]paracyclophane-4-yl)ethanoyl chloride
• 英文别名: <2.2>Paracyclophan-4-glyoxylsaeurechlorid；(±)-2-oxo-2-([2.2]paracyclophan-4-yl)ethanoyl chloride；[2.2]paracyclophane-4-glyoxyloyl chloride；2-Oxo-2-(5-tricyclo[8.2.2.24,7]hexadeca-1(13),4,6,10(14),11,15-hexaenyl)acetyl chloride
• CAS: 108869-36-9
• 化学式: C₁₈H₁₅ClO₂
• 分子量: 298.769
• InChiKey: HYXCLUXZAQKPGG-UHFFFAOYSA-N

物化性质

• 熔点：
  92 °C
• 沸点：
  465.6±55.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-oxo-2-([2.2]paracyclophane-4-yl)ethanoyl chloride 在 palladium on activated charcoal sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氢气 、 三溴化磷 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 为溶剂， 25.0~40.0 ℃ 、500.0 kPa 条件下， 反应 4.84h， 生成 4-(2-Hydroxyethyl)-<2.2>paracyclophan
  参考文献：
  名称：

  Psiorz, Manfred; Schmid, Rolf, Chemische Berichte, 1987, vol. 120, p. 1825 - 1828

  摘要：

  DOI：
• 作为产物：
  描述：

  草酰氯 、 对二甲苯二聚体 在 aluminum (III) chloride 作用下， 以 二氯甲烷 为溶剂， 生成 2-oxo-2-([2.2]paracyclophane-4-yl)ethanoyl chloride
  参考文献：
  名称：

  基于伪双取代 [2.2] 对环芳烷的多层 2D π 堆叠共轭聚合物

  摘要：

  π 系统之间的链间相互作用对共轭有机材料的电子结构有很强的影响。先前已通过分子的光谱和电化学表征探索了这种影响，其中成对的共轭低聚物通过附着在刚性支架上以堆叠的方式保持。我们制备了一种新聚合物，该聚合物使用伪双取代 [2.2] 对环芳骨架将 1,4-双(苯乙炔基)-2,5-二烷氧基苯 (PE(3)) 发色团以 pi 堆叠的方式覆盖在整个发色团上。长度和扩展的多层排列。这种新聚合物的溶液显示出 171 nm 的斯托克斯位移，相比之下仅约 30 nm 对于以前的模型，其中只有 PE(3) 生色团的末端苯环保持在堆叠排列中。这表明 pi 系统在多层组件中在其整个长度上的链间相互作用提供了激发态松弛到负责发射的稳定“幻影”电子态。这种稳定在具有较小重叠度的聚合物的堆叠二聚体或其他区域异构体中是不可用的。因此，可溶性聚合物的结构模仿了半导体薄膜中共轭聚合物链段的结构，并将为探索这些重要材料中的电荷载

  DOI：

  10.1021/ja104696e

文献信息

• New Paracyclophanylthiazoles with Anti-Leukemia Activity: Design, Synthesis, Molecular Docking, and Mechanistic Studies
  作者：Ashraf A Aly、Stefan Bräse、Alaa A. Hassan、Nasr K. Mohamed、Lamiaa E. Abd El-Haleem、Martin Nieger、Nesrin M. Morsy、Elshimaa M. N. Abdelhafez

  DOI：10.3390/molecules25133089

  日期：——

  elucidate the structure of the products. The target compounds 3a–f were screened against 60 cancer cell lines. They displayed anticancer activity against a leukemia subpanel, namely, RPMI-8226 and SR cell lines. The activity of compound 3a was found as the most cytotoxic potency against 60 cancer cell lines. Consequently, it was selected for further five doses analysis according to National Cancer Institute

  由对环芳基-酰基氨基硫脲 2a- 反应合成了一系列新的 2-(2-(4'-[2.2] 对环芳基)-肼基亚基)-3-取代-4-氧噻唑烷-5-亚基) 乙酸甲酯 3a-f f 使用乙炔二羧酸二甲酯。基于核磁共振（NMR）、红外（IR）和质谱（HRMS），阐明了所得产物的结构。X 射线结构分析也被用作阐明产品结构的明确工具。针对 60 种癌细胞系筛选了目标化合物 3a-f。它们对白血病亚组（即 RPMI-8226 和 SR 细胞系）显示出抗癌活性。发现化合物 3a 的活性是对 60 种癌细胞系最具细胞毒性的。最后，根据美国国家癌症研究所 (NCI) 的协议，它被选为进一步的五次剂量分析。细胞毒性作用在 GI50 和总生长抑制 (TGI) 水平上分别显示出介于 0.63 和 1.28 之间以及介于 0.58 和 5.89 之间的选择性比率。因此，化合物 3a 对最敏感的白血病 RPMI-8226 和
• [2.2]Paracyclophane‐Based TCN‐201 Analogs as GluN2A‐Selective NMDA Receptor Antagonists
  作者：Remya Rajan、Dirk Schepmann、Ruben Steigerwald、Julian A. Schreiber、Ehab El‐Awaad、Joachim Jose、Guiscard Seebohm、Bernhard Wünsch

  DOI：10.1002/cmdc.202100400

  日期：2021.10.15

  antagonist TCN-201 and analogs adopt a U-shaped conformation. [2.2]Paracyclophane-based GluN2A antagonists were designed to mimic the U-shaped conformation of TCN-201 in the binding pocket. The synthesized benzamide shown here possesses 36 % of the GluN2A inhibitory activity of TCN-201, confirming that compounds with the [2.2]paracyclophane system are well accepted by GluN2A-NMDA receptors.

  在结晶的 GluN1/GluN2A 配体结合结构域的结合口袋中，原型拮抗剂 TCN-201 和类似物采用 U 形构象。 [2.2]基于对环芳烷的 GluN2A 拮抗剂被设计为模拟 TCN-201 在结合袋中的 U 形构象。这里显示的合成苯甲酰胺具有 TCN-201 36% 的 GluN2A 抑制活性，证实具有 [2.2] 对环芳烷系统的化合物可以被 GluN2A-NMDA 受体很好地接受。
• Synthesis of New Planar-Chiral Linked [2.2]Paracyclophanes-N-([2.2]-Paracyclophanylcarbamoyl)-4-([2.2]Paracyclophanylcarboxamide, [2.2]Paracyclophanyl-Substituted Triazolthiones and -Substituted Oxadiazoles
  作者：Ashraf A. Aly、Stefan Bräse、Alaa A. Hassan、Nasr K. Mohamed、Lamiaa E. Abd El-Haleem、Martin Nieger

  DOI：10.3390/molecules25153315

  日期：——

  manuscript describes the synthesis of new racemic and chiral linked paracyclophane assigned as N-5-(1,4(1,4)-dibenzenacyclohexaphane-12-yl)carbamoyl)-5’-(1,4(1,4)-dibenzenacyclohexaphane-12-yl)carboxamide. The procedure depends upon the reaction of 5-(1,4(1,4)-dibenzenacyclohexaphane-12-yl)hydrazide with 5-(1,4(1,4)-dibenzenacyclohexaphane-12-yl)isocyanate. To prepare the homochiral linked paracyclophane

  该手稿描述了新的外消旋和手性连接的对环芳烷的合成，指定为 N-5-(1,4(1,4)-dibenzenacyclohexaphane-12-yl)carbamoyl)-5'-(1,4(1,4)-二苯并环六烷-12-基）甲酰胺。该过程取决于 5-(1,4(1,4)-二苯并环六烷-12-基)酰肼与 5-(1,4(1,4)-二苯并环六烷-12-基)异氰酸酯的反应。为了制备化合物的同手性连接的对环芳烷，将 5-(1,4(1,4)-dibenzenenacyclohexaphane-12-yl) 甲醛（对映体纯度 60%ee）的对映选择性氧化成相应的酸，然后氯化，得到相应的 [2.2] 对环烷的酰氯。遵循与制备外消旋氨基甲酰基相同的程序并通过 HPLC 纯化，我们成功获得了目标 Sp-Sp-N-5-(1,4(1, 4)-二苯并环六烷-12-基)氨基甲酰基)-5'-(1,4(1,4)-二苯并环六烷-12-基)甲酰胺。将
• A Fast Photochromic Molecule That Colors Only under UV Light
  作者：Yuta Kishimoto、Jiro Abe

  DOI：10.1021/ja810032t

  日期：2009.4.1

  We demonstrate that photochromism based on light-driven reversible bond cleavage can enable rapid coloration upon UV light irradiation and successive fast thermal bleaching within tens of milliseconds at room temperature. We have succeeded in developing a bisimidazole derivative with a paracyclophane moiety, pseudogem-bisDP1[2.2]PC, that changes from colorless to blue when irradiated with UV light. The incident light homolytically cleaves the C-N bond that links the two imidazole rings, generating a pair of imidazotyl radicals. A paracyclophane moiety connects the two radicals, thereby preventing them from diffusing away from one another, and the radicals quickly bind with each other to flip back to the original bisimidazole. Photochromic materials showing such intense photocoloration and fast thermal bleaching performance could be promising materials for possible fast light modulator applications.
• Diastereomers Composed of Two Planar-Chiral Subunits: Bis([2.2]paracyclophan-4-yl)methane and Analogues
  作者：Ludger Ernst、Lars Wittkowski

  DOI：10.1002/(sici)1099-0690(199907)1999:7<1653::aid-ejoc1653>3.0.co;2-r

  日期：1999.7

  A series of compounds Q(2)Z was prepared, where Q = [2.2]-paracyclophan-4-yl and Z = C(=O) (4), CH2 (5), SiMe2 (6), S (7), P(=O)OMe (8), and C(=O)C(=O) (9). Because of the planar chirality of Q, these compounds occur as meso- (m) and chiral (c) diastereomers, which were formed in equal amounts. They were separated in the cases of 4-7 and enriched in the case of 9 (diastereomeric ratio ca. 7:3). Compound 8 possesses a pseudoasymmetric phosphorus centre and occurs as one chiral (8c) and two meso diastereomers (8m(1), 8m(2)), all three of which were isolated separately. The configurations of 5m/5c, 6m/6c, and 8c were directly determined by NMR spectroscopy, that of 4m/4c indirectly by reducing the separated compounds to 5m and 5c, respectively, and that of 7m by X-ray diffraction. The favoured conformations of 4-8 were studied by molecular mechanics computations by using the MM3(94) program. An attempt was made to rationalize some chemical shift differences between diastereomers on the basis of the conformers predicted.