ethyl 1-methyl-4H-pyrrolo[3,2-b]pyrrole-5-carboxylate | 35357-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-methyl-4H-pyrrolo[3,2-b]pyrrole-5-carboxylate
• 英文别名: ethyl 4-methyl-1,4-dihydropyrrolo[3,2-b]pyrrole-2-carboxylate；4-methyl-1,4-dihydro-pyrrolo[3,2-b]pyrrole-2-carboxylic acid ethyl ester；Ethyl 4H-1-methylpyrrolo[3,2-b]pyrrole-5carboxylate
• CAS: 35357-55-2
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: BJZSJXBOHBVOKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 1-methyl-4H-pyrrolo[3,2-b]pyrrole-5-carboxylate 、 碘甲烷 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到ethyl 1,4-dimethylpyrrolo[3,2-b]pyrrole-5-carboxylate
  参考文献：
  名称：

  Di-tungsten Bis-carbene Complexes Linked by Condensed Heteroaromatic Spacers

  摘要：

  3,6-二甲基噻吩并[3,2-b]噻吩、N,N′-二甲基吡咯并[3,2-b]吡咯和N-甲基噻吩并[3,2-b]吡咯的2,7-二锂基底物与W(CO)₆反应，经过随后的乙基化反应与Et₃OBF₄，得到二钨双卡宾配合物[(CO)₅W{C(OEt)XXC(OEt)} W(CO)₅]（XX = 紧凑的杂芳烃间隔）。研究和比较了在对紧凑环进行二锂化时的攻击位点，并通过根据环中杂原子的作用改变反应条件来优化所需的二钨双卡宾配合物的产率。报告了三种二钨双卡宾配合物的晶体学数据，并比较了它们的结构特征。紧凑杂芳烃环上的甲基取代基在确定分子构型方面起着重要作用。

  DOI：

  10.1515/znb-2007-0316
• 作为产物：
  描述：

  ethyl (Z)-2-azido-3-(1-methylpyrrol-2-yl)prop-2-enoate 生成 ethyl 1-methyl-4H-pyrrolo[3,2-b]pyrrole-5-carboxylate
  参考文献：
  名称：

  ARATANI, TADATOSHI;YOSHIHARA, HIROSHI;SUZUKAMO, GOHFU, TETRAHEDRON LETT., 30,(1989) N3, C. 1655-1656

  摘要：

  DOI：

文献信息

• Di-tungsten Bis-carbene Complexes Linked by Condensed Heteroaromatic Spacers
  作者：Marilé Landmana、Helmar Görls、Chantelle Crause、Hubert Nienaber、Andrew Olivier、Simon Lotz

  DOI：10.1515/znb-2007-0316

  日期：2007.3.1

  The 2,7-dilithiated substrates of 3,6-dimethylthieno[3,2-b]thiophene, N,N′-dimethylpyrrolo[3,2- b]pyrrole and N-methylthieno[3,2-b]pyrrole were reacted with W(CO)₆ to give, after subsequent alkylation with Et₃OBF₄, the ditungsten biscarbene complexes [(CO)₅WC(OEt)XXC(OEt)} W(CO)₅] (XX = condensed heteroaromatic spacers). Sites of attack during the dilithiation of the condensed rings were studied and compared, and the yields of the desired ditungsten biscarbene complexes optimized by changing the reaction conditions according to the role of the heteroatoms in the rings. The crystallographic data of the three ditungsten biscarbene complexes are reported and their structural features compared. The methyl substituents on the condensed heteroaromatic rings play an important role in determining the molecular configurations.

  3,6-二甲基噻吩并[3,2-b]噻吩、N,N′-二甲基吡咯并[3,2-b]吡咯和N-甲基噻吩并[3,2-b]吡咯的2,7-二锂基底物与W(CO)₆反应，经过随后的乙基化反应与Et₃OBF₄，得到二钨双卡宾配合物[(CO)₅WC(OEt)XXC(OEt)} W(CO)₅]（XX = 紧凑的杂芳烃间隔）。研究和比较了在对紧凑环进行二锂化时的攻击位点，并通过根据环中杂原子的作用改变反应条件来优化所需的二钨双卡宾配合物的产率。报告了三种二钨双卡宾配合物的晶体学数据，并比较了它们的结构特征。紧凑杂芳烃环上的甲基取代基在确定分子构型方面起着重要作用。
• FLUORO-SUBSTITUTED INHIBITORS OF D-AMINO ACID OXIDASE
  申请人：Heffernan L. R. Michele

  公开号：US20080004327A1

  公开（公告）日：2008-01-03

  This invention provides novel inhibitors of the enzyme D-amino acid oxidase as well as pharmaceutical compositions including the compounds of the invention. The invention also provides methods for the treatment and prevention of neurological disorders, such as neuropsychiatric and neurodegenerative diseases, as well as pain, ataxia and convulsion. The compounds of the invention have the general structure: wherein A is NH or S. Q is a member selected from CR 1 and N. X and Y are members independently selected from O, S, CR 2 , N and NH. R 1 , R 2 and R 4 are members independently selected from H and F, provided that at least one member selected from R 1 , R 2 and R 4 is F. R 6 is a member selected from O − X + and OH, wherein X + is a positive ion, which is a member selected from inorganic positive ions and organic positive ions.

  这项发明提供了D-氨基酸氧化酶的新型抑制剂，以及包括该发明中化合物的药物组合物。该发明还提供了用于治疗和预防神经系统疾病，如神经精神病和神经退行性疾病，以及疼痛、共济失调和抽搐的方法。该发明中的化合物具有一般结构：其中A为NH或S。Q是从CR1和N中选择的成员。X和Y分别是从O、S、CR2、N和NH中独立选择的成员。R1、R2和R4是从H和F中独立选择的成员，前提是至少选择R1、R2和R4中的一个成员为F。R6是从O−X+和OH中选择的成员，其中X+是正离子，从无机正离子和有机正离子中选择的成员。
• SUBSTITUTED THIENOPYRROLE CARBOXYLIC ACID AMIDES, PYRROLOTHIAZOLE CARBOXYLIC ACID AMIDES, AND RELATED ANALOGS AS INHIBITORS OF CASEIN KINASE I
  申请人：Fink Marc David

  公开号：US20070299112A1

  公开（公告）日：2007-12-27

  The present invention discloses and claims compounds of formula (I) and formula (II), as inhibitors of human casein kinase Iε and methods for using said compounds for treating central nervous system diseases and disorders including mood disorders and sleep disorders. Pharmaceutical compositions comprising compounds of formula (I) or formula (II) and a method for the preparation of compounds of formula (I) or formula (II) are also disclosed and claimed.

  本发明揭示和声明公式(I)和公式(II)的化合物，作为人类酪蛋白激酶Iε的抑制剂，并提供使用这些化合物治疗中枢神经系统疾病和紊乱，包括情绪障碍和睡眠障碍的方法。还揭示和声明了包含公式(I)或公式(II)化合物的药物组合物，以及制备公式(I)或公式(II)化合物的方法。
• A synthesis of 4,7-dihydro-1H-dipyrrolo[3,2-b:2′,3′-d]pyrrole and 4,7-dihydro-4H-thieno[3,2-b]pyrrolo[2,3-d]pyrrole systems
  作者：Tadatoshi Aratani、Hiroshi Yoshihara、Gohfu Suzukamo

  DOI：10.1016/s0040-4039(00)99545-5

  日期：1989.1

  The titled two systems (3 and 6), both new members of linearly fused heteroaromatics, were prepared using pyrrolo-annulation reaction: condensation of an aromatic aldehyde with azidoacetate followed by thermolysis of the resulting azidoacrylate.

  标题为两个系统（3和6），都是线性稠合杂芳族化合物的新成员，是使用吡咯环化反应制备的：芳族醛与叠氮基乙酸酯的缩合反应，然后热解生成的叠氮基丙烯酸酯。
• Synthesis and fluorescence properties of unsymmetrical 1,4-dihydropyrrolo[3,2-<i>b</i>]pyrrole dyes
  作者：Yasuhiro Kubota、Kenta Koide、Yuka Mizuno、Masato Nakazawa、Toshiyasu Inuzuka、Kazumasa Funabiki、Hiroyasu Sato、Masaki Matsui

  DOI：10.1039/d1nj04663b

  日期：——

  derivative 5 showed solvatochromic fluorescence (from 393 nm in n-hexane to 446 nm in acetonitrile). In contrast, the 6-substituted derivative 6 showed locally excited fluorescence (e.g., λfl = 406 nm in n-hexane) in nonpolar solvents, twisted intramolecular charge transfer fluorescence (e.g., λfl = 538 nm in acetonitrile) in polar solvents, and dual fluorescence (e.g., λfl = 392 and 517 nm in dichloromethane)

  合成了不对称的1,4-二氢吡咯并[3,2- b ]吡咯并研究了它们的吸收和荧光特性。由于有效的供体-π-受体结构，5-对-二乙氨基苯基取代的衍生物5（λ ab = 346 nm）与6-对-二乙氨基苯基取代的衍生物6（λ ab = 308 nm）相比显示出红移的λ ab前者促进分子内电荷从二乙氨基转移到乙氧羰基。5-取代衍生物5显示出溶剂化显色荧光（从 393 nm in n-己烷至 446 nm，在乙腈中）。与此相反，6-取代的衍生物6局部地表明激发荧光（例如，λ FL = 406纳米Ñ己烷）在非极性溶剂的，扭曲的分子内电荷转移荧光（例如，λ FL在极性溶剂= 538纳米的乙腈溶液），和双荧光（例如，λ fl = 392 和 517 nm 在二氯甲烷中）在氯化溶剂中。结果，6-取代的衍生物6在极性溶剂中表现出很大的斯托克斯位移（在乙腈中高达 230 nm）。6-取代衍生物6在固态下没有表现出荧光，而