((E)-1-propenyl)-1H-pyrrole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ((E)-1-propenyl)-1H-pyrrole
• 英文别名: (E)-1-(Prop-1-enyl)pyrrole；N-[(E)-1-propenyl]pyrrole；N-methylvinylpyrrole；1-[(E)-prop-1-enyl]pyrrole
• 化学式: C₇H₉N
• 分子量: 107.155
• InChiKey: FXWBVPHFFCAGCZ-GORDUTHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-(丙-2-烯基)吡咯 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 生成 ((Z)-1-propenyl)-1H-pyrrole 、 ((E)-1-propenyl)-1H-pyrrole
  参考文献：
  名称：

  Comparison of the electronic and steric structures of 1-vinyl-and 1-(prop-1-en-1-yl)pyrroles according to the 1H and 13C NMR data

  摘要：

  According to the H-1 and C-13 NMR data, 1-isopropenylpyrroles are characterized by larger dihedral angles between the heteroring and exocyclic double bond planes, as compared to isostructural 1-vinylpyrroles, due to steric effect of the alpha-methyl group in the propenyl fragment. As a result, p-pi conjugation with the propenyl group is weaker than with the vinyl group. The propenyl group in 1-isopropenylpyrrole having no other substituents in the heteroring is forced out from the heteroring plane, while the 1-vinylpyrrole molecule is planar. If substituents are present in positions 2 and 5 of the pyrrole ring, the propenyl group on the nitrogen atom becomes orthogonal with respect to the pyrrole ring plane, so that no p-pi conjugation is possible. The steric structures of (E)-1-(prop-1-en-1-yl)pyrrole and (Z)-1-(prop-l-en-l-yl)pyrrole are different: the propenyl group in the former is turned relative to the heteroring plane, while the latter molecule is planar.

  DOI：

  10.1134/s1070428007030116

文献信息

• Heterocyclic substituted metallocene compounds for olefin polymerization
  申请人：Voskoboynikov Z. Alexander

  公开号：US20050261449A1

  公开（公告）日：2005-11-24

  This invention relates to compounds represented by formula: wherein M is a group 3, 4, 5 or 6 transition, lanthanide, or actinide metal atom; E is an indenyl ligand substituted in any position with at least one aromatic or pseudoaromatic heterocyclic substituent that is bonded to the indenyl ring through a nitrogen or phosphorous ring heteroatom; A is a substituted or unsubstituted cyclopentadienyl, heterocyclopentadienyl, indenyl, heteroindenyl, fluorenyl, or heterofluorenyl ligand, or other mono-anionic ligand, or A may, independently, be E; Y is an optional bridging group; y is zero or one; X are, independently, univalent anionic ligands, and provided that when A is E, and y is one, and Y is bonded to the one position of each indenyl ligand, and per indenyl ligand there is only one aromatic heterocyclic or pseudoaromatic heterocyclic that is bonded to the indenyl ligand.

  本发明涉及以下式表示的化合物： 其中，M是3、4、5或6族过渡金属、镧系金属或锕系金属原子；E是任何位置上至少带有一种芳香或伪芳香杂环取代基的茚基配体，该取代基通过氮或磷杂环原子与茚环相连；A是取代或未取代的环戊二烯基、杂环戊二烯基、茚基、杂茚基、芴基或杂芴基配体，或其他单阴离子配体，或A可以独立地是E；Y是可选的桥接基团；y为零或一；X是独立的一价阴离子配体，且当A为E，y为一，并且Y与每个茚基配体的一位置相连时，每个茚基配体仅与一个芳香杂环或伪芳香杂环相连。
• Verfahren zur Herstellung von Iminen und Enaminen und gegebenenfalls deren Weiterhydrierung zu Aminen
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0982293A1

  公开（公告）日：2000-03-01

  Verfahren zur Herstellung von Iminen und/oder Enaminen durch Anlagerung von Ammoniak, primären Aminen oder sekundären Aminen an Acetylene und/oder Allene, bei denen man die Umsetzung in der Gasphase bei erhöhter Temperatur in Gegenwart von einem amorphes und/oder kristallines Zink- und/oder Cadmiumsilikat enthaltenden Heterogenkatalysator durchführt.

  将氨、伯胺或仲胺加到炔和/或烯中制备亚胺和/或烯胺的工艺，其中反应在气相中于高温下在含有无定形和/或结晶锌和/或硅酸镉的异相催化剂存在下进行。
• ——
  作者：B. A. Trofimov、O. A. Tarasova、M. A. Shemetova、A. V. Afonin、L. V. Klyba、L. V. Baikalova、A. I. Mikhaleva

  DOI：10.1023/a:1025502016921

  日期：——

  A number of previously unknown N-isopropenyl-substituted pyrroles, indoles, and di- and -triazoles were synthesized in 20-86% yield by reaction of the corresponding azole with an equilibrium mixture of propyne with allene or pure propyne and allene in the system KOH-DMSO (105-145degreesC, 5-15 h, atmospheric or elevated pressure). The reaction is regioselective. The electronic and steric structure and the degree of conjugation between the exocyclic double bond and the azole ring are discussed on the basis of the H-1 and C-13 NMR spectra. Almost complete absence of p-pi conjugation in alpha,alpha'-disubstitutecl N-isopropenylazoles have been found.
• Tarasova; Shmidt; Albanov, Russian Journal of Organic Chemistry, 1999, vol. 35, # 10, p. 1499 - 1502
  作者：Tarasova、Shmidt、Albanov、Mikhaleva、Brandsma、Trofimov

  DOI：——

  日期：——
• US7276567B2
  申请人：——

  公开号：US7276567B2

  公开（公告）日：2007-10-02