1-甲基-2-[(1-甲基吡咯-2-基)甲基]吡咯 | 81263-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-甲基-2-[(1-甲基吡咯-2-基)甲基]吡咯
• 英文名称: N,N'-dimethyldipyrromethane
• 英文别名: 1-methyl-2-[(1-methyl-1H-pyrrol-2-yl)methyl]-1H-pyrrole；1-methyl-2-[(1-methylpyrrol-2-yl)methyl]pyrrole
• CAS: 81263-87-8
• 化学式: C₁₁H₁₄N₂
• mdl: MFCD16875702
• 分子量: 174.246
• InChiKey: GIRSHINZLWWKIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  9.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-甲基-2-[(1-甲基吡咯-2-基)甲基]吡咯 在 rhodium contaminated with carbon 、 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、10.0 MPa 条件下， 反应 96.0h， 以85%的产率得到bis(1-methylpyrrolidin-2-yl)methane
  参考文献：
  名称：

  C桥联双吡咯烷和双哌啶为新配体

  摘要：

  描述了作为新型配体的亚甲基桥接的C 2对称氮杂环的制备，包括脂族和芳族体系。非对映异构体的分离以及这些配体的铜配合物在环丙烷化反应中的应用证明了这些新型配体的适用性

  DOI：

  10.1002/ejoc.201801075
• 作为产物：
  描述：

  双(1-甲基吡咯-2-基)甲酮 在 吗啉 、 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以81%的产率得到1-甲基-2-[(1-甲基吡咯-2-基)甲基]吡咯
  参考文献：
  名称：

  Groot, J. A. de; Steen, R. van der; Fokkens, R., Recueil des Travaux Chimiques des Pays-Bas, 1982, vol. 101, # 1, p. 35 - 40

  摘要：

  DOI：

文献信息

• Mannich reactions of π-excessive heterocycles using bis-(dialkylamino)methanes and alkoxydialkylaminomethanes activated with acetyl chloride or sulphur dioxide
  作者：Stephen C Eyley、Harry Heaney、George Papageorgiou、Robert F Wilkins

  DOI：10.1016/0040-4039(88)85070-6

  日期：1988.1

  Π-Excessive heterocycles react rapidly with bis(dialkylamino)methanes (aminals) and alkoxydialkylaminomethanes (aminol ethers) in acetonitrile to afford Mannich bases in good yields when activated by means of an acidic reagent such as acetyl chloride or sulphur dioxide: the principal compound studied was -methylpyrrole.

  过量的杂环与乙腈中的双（二烷基氨基）甲烷（缩醛）和烷氧基二烷基氨基甲烷（氨基醚）迅速反应，当通过酸性试剂（如乙酰氯或二氧化硫）活化时，可以高收率得到曼尼希碱。是-甲基吡咯。
• Copper(ii)-catalyzed C–H (sp3) oxidation and C–N cleavage: synthesis of methylene-bridged compounds using TMEDA as a carbon source in water
  作者：Dan Zhao、Yue Wang、Min-Xue Zhu、Qi Shen、Lei Zhang、Yun Du、Jian-Xin Li

  DOI：10.1039/c3ra40695d

  日期：——

  A green, simple, and efficient protocol for the selective methylenation via CuCl2/oxygen-mediated C–H (sp3) oxidation and C–N cleavage using tetramethylethylenediamine (TMEDA) as a carbon source has been developed. The reactions were achieved in green solvent water under atmospheric conditions. The protocol exhibited a broad substrate scope including indoles, anilines, pyrroles and 1,3-dicarbonyls. Furthermore, two key intermediates of the reaction were successfully identified and the mechanism was explored.

  以四甲基乙二胺（TMEDA）为碳源，通过 CuCl2/氧气介导的 CâH (sp3) 氧化和 CâN 裂解进行选择性亚甲基化的绿色、简单而高效的方案已经开发出来。反应在大气条件下的绿色溶剂水中进行。该方案的底物范围很广，包括吲哚、苯胺、吡咯和 1,3-二羰基。此外，还成功鉴定了反应的两个关键中间体，并探索了反应机理。
• METHOD FOR THE HYDROFORMYLATION OF OLEFINS
  申请人：Sigl Marcus

  公开号：US20100048959A1

  公开（公告）日：2010-02-25

  The present invention relates to a process for preparing hydroformylation products of olefins having at least four carbon atoms, in which a high proportion of both the linear C i -olefins having a terminal double bond comprised in the olefin-comprising feed used and of the linear C i -olefins having an internal double bond is converted into hydroformylation products. Furthermore, the invention relates to a process for preparing 2-propylheptanol which comprises such a hydroformylation process.

  本发明涉及一种制备至少具有四个碳原子的烯烃的羰基化产物的过程，其中将含有末端双键的线性C1-烯烃和含有内部双键的线性C1-烯烃的高比例转化为羰基化产物。此外，本发明涉及一种制备2-丙基庚醇的方法，其中包括这样的羰基化过程。
• New Melanoidin-like Maillard Polymers from 2-Deoxypentoses
  作者：Roland Tressl、Georg T. Wondrak、Ralph-Peter Krüger、Dieter Rewicki

  DOI：10.1021/jf970657c

  日期：1998.1.1

  In the 2-deoxy-D-ribose/methyl 4-aminobutyrate Maillard system a trapped N-substituted 2-(hydroxymethyl)pyrrole is one of the major products. However, nontrapped representatives of this type of compound were hitherto not found in other Maillard model systems, indicating their extraordinary reactivity. Model experiments with 2-deoxy-D-ribose/methylamine enabled the detection of N-methyl-2-(hydroxymethyl)pyrrole (1) and some derived linear oligomers (2, 3) as minor components. Consequently, 1 was synthesized and its oligomerization studied under very mild acidic conditions. The deformylated dimeric bis(N-methyl-2-pyrrolyl)methane (2) and trimeric N-methyl-2,5-bis(N-methyl-2-pyrrolylmethyl)pyrrole (3) were characterized by GC/MS and NMR. Higher regular oligomers up to 6 N-methyl-2-pyrrolylmethyl units as well as corresponding dehydro-oligomers up to 12 units were identified by MALDI-TOF-MS. A complementary experiment starting with N-methyl-2-hydroxy[C-13]methylpyrrole ([(CH2OH)-C-13]-1) confirmed the structure and the oligomerization pathway. The possible significance of this type of model oligomer for the melanoidin formation in Maillard reactions is discussed. The antioxidative activity of the isolated dimer and trimer was tested in Fe(III)-thiocyanate and DPPH assays.
• An unprecedented regioselective lithiation of dipyrromethanes. Synthesis of meso-functionalized dipyrromethanes
  作者：Kamaljit Singh、Amit Sharma

  DOI：10.1016/j.tetlet.2006.11.056

  日期：2007.1

  Functionalization of meso-positions of dipyrromethanes, gives valuable intermediates through a highly regioselective lithiation-substitution sequence. (c) 2006 Elsevier Ltd. All rights reserved.