1-isopropenyl-1H-pyrrole | 258832-42-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-isopropenyl-1H-pyrrole
• 英文别名: 1-isopropenylpyrrole；N-isopropenylpyrrole；N-2-Propenylpyrrole；1H-Pyrrole, 1-(1-methylethenyl)-；1-prop-1-en-2-ylpyrrole
• CAS: 258832-42-7
• 化学式: C₇H₉N
• 分子量: 107.155
• InChiKey: WIZPWTOFPFQRKV-UHFFFAOYSA-N

物化性质

• 沸点：
  126.9±13.0 °C(Predicted)
• 密度：
  0.85±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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

• 作为反应物：
  描述：

  1-isopropenyl-1H-pyrrole 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以21%的产率得到1-(3-iodoprop-1-en-2-yl)-1H-pyrrole
  参考文献：
  名称：

  Towards Rare-Functionalized N-Alkenyl-1H-pyrroles via Regioselectively Metalated N-Isopropenyl-1H-pyrroles

  摘要：

  摘要：研究了使用超碱对N-异丙烯基-1H-吡咯进行去质子化金属化反应，然后用各种电子亲和试剂捕捉的方法，作为1H-吡咯区域选择性官能化的有效工具。

  DOI：

  10.1055/a-1736-4200
• 作为产物：
  描述：

  吡咯 、 丙炔 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以59%的产率得到1-isopropenyl-1H-pyrrole
  参考文献：
  名称：

  A Novel Facile Synthesis of 2,5-Di- and 2,3,5-Trisubstituted Pyrroles

  摘要：

  在 MOR/DMSO（M = K、Cs；R = H、t-Bu）超基体系中，酮肟与丙炔或烯的异环化反应首次完成，该反应可生成 2-烷基（芳基、庚基）-5-甲基和 2,3-二烷基-5-甲基吡咯或 2-甲基-4,5,6,7-四氢吲哚，收率高达 63%。该反应大多具有区域选择性，主要或完全生成 2,5-二和 2,3,5-三取代的吡咯。在大多数情况下，次要异构体是相应的 2,4- 二和 2,3,4- 三取代吡咯，只有在乙酮肟的情况下，异构体比例约为 1:1。在甲基异丙基酮和频哪酮的肟中，4-甲基异构体占主导地位（分别为 78%和 83%）。

  DOI：

  10.1055/s-2000-7618

文献信息

• Regioselective Cross-Coupling of 1-Vinylpyrroles with Acylbromoacetylenes on Al₂O₃: Synthesis of 2-(2-Acylethynyl)-1-vinylpyrroles
  作者：B. Trofimov、L. Sobenina、Z. Stepanova、I. Ushakov、O. Petrova、O. Tarasova、K. Volkova、A. Mikhaleva

  DOI：10.1055/s-2007-965884

  日期：2007.2

  1-Vinyl- and 1-isopropenylpyrroles enter readily (ambient temperature) into cross-coupling reaction with acylbromoacet­ylenes on Al2O3 to furnish regioselectively 2-(2-acylethynyl)-1-vinyl- and 2-(2-acylethynyl)-1-isopropenylpyrroles in 39-70% yield.

  1-乙烯基-和1-异丙烯基吡咯很容易（环境温度）与Al2O3上的酰基溴乙炔发生交叉偶联反应，从而区域选择性地提供2-(2-酰基乙炔基)-1-乙烯基-和2-(2-酰基乙炔基)-1-异丙烯基吡咯产率 39-70%。
• CONJUGATED DIENE POLYMER PRODUCTION METHOD, AND CONJUGATED DIENE POLYMER COMPOSITION PRODUCTION METHOD
  申请人：Sumitomo Chemical Company, Limited

  公开号：US20150005440A1

  公开（公告）日：2015-01-01

  A method for producing a conjugated diene-based polymer is provided, in which compounds of formulas (2) and (3) and a conjugated diene compound are polymerized using a compound of formula (1), and then a compound containing a nitrogen atom and/or a silicon atom is reacted with an active end of the polymer formed via the polymerization, R 11 represents a hydrocarbylene group, R 12 and R 13 each represent an optionally substituted hydrocarbyl group or a trihydrocarbylsilyl group, or R 12 is bonded to R 3 and the group in which R 12 is bonded to R 13 represents a hydrocarbylene group optionally having a nitrogen and/or oxygen atom, —Si(R 14 ) 2 —(CH 2 ) x —Si(R 14 ) 2 —, or —Si(R 15 ) 2 —(CH 2 ) y − , and M represents an alkali metal atom, E 2 -A 2 (2) E 3 -A 3 (3) E 2 and E 3 each represent a hydrocarbyl group having a polymerizable carbon-carbon double bond, A 2 represents a substituted amino group or a nitrogen-containing heterocyclic group, and A 3 represents a substituted silyl group.

  提供一种制备基于共轭二烯的聚合物的方法，其中使用式(1)的化合物聚合式(2)和(3)的化合物以及共轭二烯化合物，然后使用含有氮原子和/或硅原子的化合物与通过聚合形成的聚合物的活性末端反应。其中，R11代表烃基烷基，R12和R13分别代表可选取代的烃基或三烷基硅基，或者R12与R3结合，R12与R13结合的基团可选地具有氮和/或氧原子，-Si(R14)2-(CH2)x-Si(R14)2-，或-Si(R15)2-( )y-，M代表碱金属原子，E2-A2(2)E3-A3(3)中，E2和E3分别代表具有可聚合碳-碳双键的烃基，A2代表取代的氨基或含氮杂环基团，A3代表取代的硅基。
• TREAD RUBBER COMPOSITION AND PNEUMATIC TIRE
  申请人：Sumitomo Rubber Industries, Ltd.

  公开号：EP2857446A1

  公开（公告）日：2015-04-08

  Provided are a tread rubber composition that can achieve a balanced improvement in fuel economy, wet-grip performance, and abrasion resistance, and a pneumatic tire including the composition. The tread rubber composition includes: a rubber component; silica; and a silane-coupling agent containing a mercapto group, the rubber component including per 100% by mass thereof 5% by mass or more of a conjugated diene polymer (A), the polymer (A) including a monomer unit derived from a conjugated diene, a monomer unit derived from a compound of formula (1), and a monomer unit derived from a compound of formula (2), at least one end of the copolymer (A) being modified by the following compound (G) or an alkoxysilane compound, the composition including 5-150 parts by mass of the silica per 100 parts by mass of the rubber component, Compound (G): at least one compound selected from the group consisting of compounds containing an optionally-substituted amino group and a carbonyl group and compounds containing an optionally-substituted amino group and a thiocarbonyl group,         V1-S1     (1)         V2-A2     (2) wherein V1 and V2 each represent a hydrocarbyl group containing a polymerizable carbon-carbon double bond; S1 represents a substituted silyl group, and A2 represents a substituted amino group or a nitrogen-containing heterocyclic group.

  本文提供了一种可均衡改善燃油经济性、湿抓地性能和耐磨性的胎面橡胶组合物，以及一种包含该组合物的充气轮胎。胎面橡胶组合物包括橡胶成分；白炭黑和含有巯基的硅烷偶联剂，橡胶成分包括每 100% 质量中 5%（质量）或更多的共轭二烯聚合物 (A)，聚合物 (A) 包括衍生自共轭二烯的单体单元、衍生自式 (1) 化合物的单体单元和源自式（2）化合物的单体单元，共聚物（A）的至少一端由下列化合物（G）或烷氧基硅烷化合物改性，该组合物包括每 100 份（质量）橡胶成分中含 5-150 份（质量）二氧化硅的化合物（G）：至少一种选自以下组别的化合物：含有任选取代的氨基和羰基的化合物，以及含有任选取代的氨基和硫代羰基的化合物、 V1-S1 (1) V2-A2 (2) 其中 V1 和 V2 分别代表含有可聚合碳碳双键的烃基，S1 代表取代的硅烷基，A2 代表取代的氨基或含氮杂环基。
• Modified conjugated diene polymer, and polymer composition containing said polymer
  申请人：SUMITOMO CHEMICAL COMPANY, LIMITED

  公开号：US10118973B2

  公开（公告）日：2018-11-06

  There is disclosed a modified conjugated diene polymer including a structural unit derived from a compound represented by formula (1), and a structural unit derived from a conjugated diene. When n is 0, at least two of R11, R12, R13, R16, R17 and R18 are substituted amino groups, and at least one is a hydroxy group or hydrocarbyloxy group.

  本发明公开了一种改性共轭二烯聚合物，包括一个由式（1）所代表的化合物衍生的结构单元和一个由共轭二烯衍生的结构单元。 当 n 为 0 时，R11、R12、R13、R16、R17 和 R18 中至少有两个是取代的氨基，至少有一个是羟基或羟基羰基。
• 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
  作者：A. V. Afonin、I. A. Ushakov、D. E. Simonenko、O. A. Tarasova、M. A. Maksimova、B. A. Trofimov

  DOI：10.1134/s1070428007030116

  日期：2007.3

  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.