3,3''-diformyl-p-terphenyl | 341556-92-1

• 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: 3,3''-diformyl-p-terphenyl
• 英文别名: [3,3''-(1,1':4',1''-terphenyl)]dicarboxaldehyde；1,4-bis(3-formylphenyl)benzene；4'-(3-Formylphenyl)-[1,1'-biphenyl]-3-carbaldehyde；3-[4-(3-formylphenyl)phenyl]benzaldehyde
• CAS: 341556-92-1
• 化学式: C₂₀H₁₄O₂
• 分子量: 286.33
• InChiKey: GILFUNUROHDJOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3,3''-diformyl-p-terphenyl 在 哌啶 、 吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 C₅₂H₃₈Cl₂F₆N₄O₈
  参考文献：
  名称：

  带有3，3′-亚芳基双丙烯酰基作为接头的新型癸二环丙烷[c]吡咯并[3，2-e]吲哚双烷基化剂。

  摘要：

  我们合成了新型山高环丙烷[c]吡咯并[3,2-e]吲哚（CPI）双烷基化剂并评估了其抗肿瘤活性。在这些衍生物中，发现其中11a（AT-760）的两个Seco 3-甲氧基羰基-2-三氟甲基CPI（MCTFCPI）部分与3,3'-（1,4-亚苯基）双丙烯酰基相连。分别对HeLaS3人子宫颈癌细胞和结肠26腺癌细胞具有比8（bizelesin，U-77,779）更强的细胞毒性和抗肿瘤活性。还显示出与化合物8或丝裂霉素C（MMC）相比，化合物11a在人结肠CX-1模型中表现出改善的体内功效。发现11a的有效剂量比8a的有效剂量低2倍。

  DOI：

  10.1021/jm000107x
• 作为产物：
  描述：

  1,4-苯二硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 二氟化氢钾 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 生成 3,3''-diformyl-p-terphenyl
  参考文献：
  名称：

  基于一锅双 Suzuki-Miyaura 偶联物的共轭三（杂）芳基衍生物的合成，使用双功能亚苯基-1,4-双（三氟硼酸）二钾

  摘要：

  描述了双官能亚苯基-1,4-双（三氟硼酸钾）与芳基和杂芳基溴化物之间的高效一锅双 Suzuki-Miyaura 交叉偶联反应。还探讨了这种方法的范围和局限性，可以合成三（杂）芳基衍生物，可能用作药物和材料科学领域。

  DOI：

  10.1055/s-0030-1260581

文献信息

• High yielding self-assembly favored by preorganization
  作者：Chi Zhang、Tianyu Jiao、Lu Tong、Hongye Wang、Yuanjiang Pan、Hao Li

  DOI：10.1039/d0cc00898b

  日期：——

  A series of macrocyclic molecules were self-assembled via imine condensation. Their yields result from preorganization of the precursors.

  一系列大环分子通过亚胺缩合自组装形成。它们的产率是由前体的预组织所决定的。
• Access to Amide‐Linked Organic Cages by in situ Trapping of Metastable Imine Assemblies: Solution Phase Bisamine Recognition
  作者：Keith G. Andrews、Kirsten E. Christensen

  DOI：10.1002/chem.202300063

  日期：——

  majority of shape-persistent self-assembled organic cages are accessed via precipitation and studied in the solid state. Herein, we show that metastable imine cages (unsuitable for precipitation) can be trapped directly by in situ Pinnick oxidation conditions, yielding soluble, robust amide cages. Unlike the by-passed imine cages, the resulting cages are tolerant of hydrolysis conditions to unmask internal

  大多数形状持久的自组装有机笼是通过沉淀获得的，并在固态下进行研究。在此，我们表明亚稳态亚胺笼（不适合沉淀）可以通过原位 Pinnick 氧化条件直接捕获，产生可溶性、坚固的酰胺笼。与旁路亚胺笼不同，由此产生的笼能够耐受水解条件以暴露内部羧酸，这些羧酸会与胺（不适合亚胺笼的客体）发生 2 点结合。
• Enantioselective and Diastereoselective Molecular Recognition of Cyclic Dipeptides by a C2 Macrolactam Host
  作者：Michael F. Cristofaro、A. Richard Chamberlin

  DOI：10.1021/ja00091a010

  日期：1994.6

  Two synthetic, optically active, C-2 symmetric macrolactam hosts 11b and 11c have been synthesized from L-leucine, and other simple starting materials, in an 11-step, convergent synthesis. These new macrocycles, which were conceived with the aid of current molecular modeling software, were designed to complex neutral amides in organic solvents through complementary intermolecular hydrogen bonding. The hosts, which are made up of two short peptide strands alternately interlinked with two rigid aromatic spacer units to form a large macrocyclic structure, feature a binding site that consists of a convergent, ordered array of amide functions. H-1 NMR and solution FT-IR spectroscopy demonstrated that in CDCl3 11b and 11c each bound the five various stereoisomers of the cyclic dipeptides cycle-Gly-Leu and cyclo-Leu-Leu, with association constants ranging from 70 to 2260 M(-1) (+/-15%). 11b was capable of moderately high enantioselective and diastereoselective molecular recognition (Delta Delta(enan) = 0.97-1.23 kcal/mol, Delta Delta G(dia) = 0.28-0.95 kcal/mol) of the various chiral diketopiperazines and preferred guests bearing one or more side chains of the L configuration. In contrast, the diastereomeric host 11c showed very little enantioselectivity (Delta Delta G(enan) = 0.09-0.17 kcal/mol), but did show diastereoselectivity (Delta Delta G(dia) = 0.44-0.54 kcal/mol) and showed a modest preference for guests with side chains of the D configuration. Molecular modeling studies, as well as H-1 NMR data, suggest that these hosts are conformationally flexible and bind to the guests with an induced-fit mechanism. The host-guest complexes are stabilized through the formation of three to four intermolecular amide-amide hydrogen bonds in the binding cavity of the macrocycle as well as favorable van der Waals contacts between the hydrocarbon surfaces of the host and guest. The stereoselective binding observed is most likely due to the slight energetic differences in the intermolecular hydrogen bonding patterns that stabilize the host-guest complexes, which are in turn due to the varying degrees of steric interactions that occur between the side chains of the guest and of the host. It is anticipated that the strength, and the degree, of the selectivity in binding of the guests by hosts 11b,c could be improved upon through additional structural modifications.
• US3948861A
  申请人：——

  公开号：US3948861A

  公开（公告）日：1976-04-06
• Novel Seco Cyclopropa[<i>c</i>]pyrrolo[3,2-<i>e</i>]indole Bisalkylators Bearing a 3,3‘-Arylenebisacryloyl Group as a Linker
  作者：Yasumichi Fukuda、Shigeki Seto、Hirosuke Furuta、Hiroyuki Ebisu、Yasuo Oomori、Shiro Terashima

  DOI：10.1021/jm000107x

  日期：2001.4.1

  We synthesized the novel seco cyclopropa[c]pyrrolo[3,2-e]indole (CPI) bisalkylators and evaluated their antitumor activity. Among these derivatives, 11a (AT-760), in which the two seco 3-methoxycarbonyl-2-trifluoromethyl CPI (MCTFCPI) moieties are connected with a 3,3'-(1,4-phenylene)bisacryloyl group, was found to exhibit more potent cytotoxicity and antitumor activity against HeLaS3 human uterine

  我们合成了新型山高环丙烷[c]吡咯并[3,2-e]吲哚（CPI）双烷基化剂并评估了其抗肿瘤活性。在这些衍生物中，发现其中11a（AT-760）的两个Seco 3-甲氧基羰基-2-三氟甲基CPI（MCTFCPI）部分与3,3'-（1,4-亚苯基）双丙烯酰基相连。分别对HeLaS3人子宫颈癌细胞和结肠26腺癌细胞具有比8（bizelesin，U-77,779）更强的细胞毒性和抗肿瘤活性。还显示出与化合物8或丝裂霉素C（MMC）相比，化合物11a在人结肠CX-1模型中表现出改善的体内功效。发现11a的有效剂量比8a的有效剂量低2倍。