4,4'-diethyl-3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2-carbaldehyde | 967-68-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4'-diethyl-3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2-carbaldehyde
• 英文别名: 3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrrylmethane-5,5'-dicarboxaldehyde；5,5’-methylenebis(4-ethyl-3-methyl-1H-pyrrole-2-carbaldehyde)；5,5′-methylenebis(4-ethyl-3-methyl-1H-pyrrole-2-carbaldehyde)；3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrrylmethane-5,5'-dialdehyde；5,5'-diformyl-4,4'-dimethyl-3,3'-diethyl-2,2'-dipyrrolylmethane；5,5'-diformyl-3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrrylmethane；1H-Pyrrole-2-carboxaldehyde, 5,5'-methylenebis[4-ethyl-3-methyl-；4-ethyl-5-[(3-ethyl-5-formyl-4-methyl-1H-pyrrol-2-yl)methyl]-3-methyl-1H-pyrrole-2-carbaldehyde
• CAS: 967-68-0
• 化学式: C₁₇H₂₂N₂O₂
• 分子量: 286.374
• InChiKey: OGOATYJXXAAJJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  65.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-diethyl-3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2-carbaldehyde 在 氢溴酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 zinc(II) 10-phenyl-2,18-diethyl-3,17-dimethylporphyrinate
  参考文献：
  名称：

  Complexation of zinc(II) and ruthenium(II) porphyrinates with methyl glycinate and methyl m-aminobenzoate

  摘要：

  Zinc(II) and ruthenium(II) monohydroxyporphyrinates with a different arrangement of the reaction center in the meso-aryl moiety of the macrocycle were synthesized, and their ability of complexing with the methyl esters of glycine and m-aminobenzoic acid in toluene were studied using the methods of spectrophotometric titration and H-1 NMR spectroscopy. The stability constants of the resulting complexes and concentration ranges of their existence were determined.

  DOI：

  10.1134/s1070363213050204
• 作为产物：
  描述：

  5,5-亚甲基双(4-乙基-3-甲基-2-吡咯羧酸二乙酯) 在 sodium hydroxide 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 4,4'-diethyl-3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  Simple Methodology for the Synthesis of meso-Unsubstituted β-Substituted Alkyl Porphyrins

  摘要：

  无内消旋的β-烷基二吡咯甲烷与不同的无内消旋的1,9-双(甲酰基)二吡咯甲烷的麦克唐纳[2+2]型缩合产生新的不对称空间无阻碍的卟啉。

  DOI：

  10.1055/s-2006-950263

文献信息

• Synthesis and Structure–Activity Relationships of Tambjamines and B-Ring Functionalized Prodiginines as Potent Antimalarials
  作者：Papireddy Kancharla、Jane Xu Kelly、Kevin A. Reynolds

  DOI：10.1021/acs.jmedchem.5b00560

  日期：2015.9.24

  Synthesis and antimalarial activity of 94 novel bipyrrole tambjamines (TAs) and a library of B-ring functionalized tripyrrole prodiginines (PGs) against a panel of Plasmodium falciparum strains are described. The activity and structure–activity relationships demonstrate that the ring-C of PGs can be replaced by an alkylamine, providing for TAs with retained/enhanced potency. Furthermore, ring-B of

  描述了94种新型联吡咯他布明胺（TAs）的合成和抗疟活性以及针对一系列恶性疟原虫菌株的B环功能化三联吡咯酮（PGs）库。活性和结构-活性之间的关系表明，PGs的C环可以被烷基胺取代，从而为TAs提供保留/增强的效力。此外，PG / TA的B环可以在4位（取代OMe）或3位和4位上被短烷基取代而不影响效能。已评估了八个代表性TA和两个PG对耐多药疟原虫的抗疟活性口服给药的小鼠剂量范围为5-100 mg / kg×4天。KAR425 TA的功效比以前任何PG所观察到的都要大，在25天和50 mg / kg×4天的剂量下，直到28天之前，对感染疟疾的小鼠提供100％的保护，并且在该模型中也可以单次口服治疗（80毫克/公斤）。这项研究提出了TAmbjamines中抗疟活性的第一个解释。
• [EN] TAMBJAMINES AND B-RING FUNCTIONALIZED PRODIGININES<br/>[FR] TAMBJAMINES ET PRODIGININES FONCTIONNALISÉES À CYCLE B
  申请人：UNIV PORTLAND STATE

  公开号：WO2016176450A1

  公开（公告）日：2016-11-03

  Embodiments of tambjamines and B-ring functionalized prodiginines are disclosed. Methods of synthesizing and using the disclosed compounds are also disclosed. Some embodiments of the disclosed compounds have antimalarial activity. Certain embodiments of the disclosed compounds have been shown to clear parasitemia in mice, and/or are curative in a single dose without toxicity.

  本文披露了tambjamine和B环功能化的prodiginines的实施例。还披露了合成和使用所披露化合物的方法。所披露化合物的一些实施例具有抗疟活性。已经证明所披露化合物的某些实施例能够清除小鼠体内的寄生虫，或者在单剂量下具有治愈作用且无毒性。
• Electron transfer in bis-porphyrin donor-acceptor compounds with polyphenylene spacers shows a weak distance dependence
  作者：Anna Helms、David Heiler、George McLendon

  DOI：10.1021/ja00041a047

  日期：1992.7

  containing one, two, or three phenyl bridges. Complete synthetic details are provided. For studies of photochemical electron transfer, mixed metals were incorporated, with zinc in one porphyrin macrocycle and Fe III (bis-imidazole) in the other macrocycle. When photoexcited, an electron is transferred from Zn to Fe III

  已经合成了一系列亚苯基桥连的双卟啉加合物，包含一个、两个或三个苯桥。提供了完整的合成细节。为了研究光化学电子转移，加入了混合金属，锌在一个卟啉大环中，而 Fe III（双咪唑）在另一个大环中。当光激发时，一个电子从 Zn 转移到 Fe III
• Porphyrins with exocyclic rings. Part 12. Synthesis of meso,β-butano- and meso,β-pentanoporphyrins from cycloalka[b]pyrroles
  作者：Jolie A. Bastian、Timothy D. Lash

  DOI：10.1016/s0040-4020(98)00327-5

  日期：1998.6

  Knorr-type condensations with cycloheptanone or cyclooctanone, respectively. Treatment with lead tetraacetate in dichloromethane afforded the labile ω-acetates 8 and subsequent acid catalyzed condensation with α-unsubstituted pyrrole-2-carboxylates yielded the related pyrrolylcycloalka[b]pyrroles 29 and 30. The α-unsubstituted pyrroles 14 and 23 were prepared by condensing α,β-unsubstituted ketones, or their

  具有b面稠合的七元或八元碳环的吡咯5分别通过与环庚酮或环庚酮的克诺尔缩合反应以高收率制备。在二氯甲烷中用四乙酸铅处理得到不稳定的ω-乙酸酯8，随后酸催化与α-未取代的吡咯-2-羧酸酯的缩合反应，产生了相关的吡咯基环烷基[b]吡咯29和30。α-未取代的吡咯14和23的制备方法是：在DBU存在下，将N，甲苯磺酰基苄基乙酸酯与α，β-未取代的酮或其β-乙酰氧基羰基前体缩合，然后用POCl 3脱水。-吡啶和碱催化消除对甲苯磺酸。将二吡咯二苄基酯29和30在10％Pd-C上氢解，得到相应的二羧酸。在改良的MacDonald“ 2 + 2”条件下，酸与二甲酰基二吡咯基甲烷33的缩合反应得到一系列带有7或8元环外环的四个环烷卟啉4a-d。尽管以良好的产率分离出内消旋的β-丁卟啉4a和4b，但相关的内消旋的β-五杂卟啉4c和4d的结果却较差。。有人提出，八元碳环会扭曲开环四吡咯中间体的几何形状，这种有害影响导致所观察到的较低收率。
• Synthesis and characterization of novel cobalt aluminum cofacial porphyrins. First crystal and molecular structure of a heterobimetallic biphenylene pillared cofacial diporphyrin
  作者：Roger Guilard、Michel Angel Lopez、Alain Tabard、Philippe Richard、Claude Lecomte、Stephane Brandes、James E. Hutchison、James P. Collman

  DOI：10.1021/ja00051a021

  日期：1992.12

  The synthesis of the novel family of heterodinuclear complexes (DP)CoAl(OR) (where DP 4- is the tetraanion of the diporphyrin biphenylene DPB or the diporphyrin anthracene DPA, and R=CH 3 , CH 2 CH 3 , or CH 2 C 6 H 5 ) is reported. These complexes were obtained by selective metalation of the cofacial diporphyrins with cobalt and aluminium. Each (DP)CoAl(OR) complex was characterized by mass spectrometry

  新型异双核配合物家族 (DP)CoAl(OR) 的合成（其中 DP 4- 是双卟啉联苯 DPB 或双卟啉蒽 DPA 的四阴离子，并且 R=CH 3 、CH 2 CH 3 或 CH 2 C 6 H 5 ) 被报道。这些配合物是通过用钴和铝对共面二卟啉进行选择性金属化而获得的。每个 (DP)CoAl(OR) 复合物都通过质谱和 UV-vis、IR、ESR 和 1 H NMR 光谱进行表征。