1-异丙基-2,3,4,5-四甲基-1H-吡咯 | 115695-70-0

• 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-异丙基-2,3,4,5-四甲基-1H-吡咯
• 英文名称: 1-(1-methylethyl)-2,3,4,5-tetramethylpyrrole
• 英文别名: 2,3,4,5-Tetramethyl-1-propan-2-ylpyrrole
• CAS: 115695-70-0
• 化学式: C₁₁H₁₉N
• mdl: MFCD18809996
• 分子量: 165.279
• InChiKey: VPIRGKXUPXGFDG-UHFFFAOYSA-N

物化性质

• 沸点：
  249.9±9.0 °C(Predicted)
• 密度：
  0.88±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.636
• 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：

  2,3,5,6-四溴对二甲苯 、 1-异丙基-2,3,4,5-四甲基-1H-吡咯 在 正丁基锂 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 3.0h， 以65%的产率得到1,3,5,6,7,8,10,12,13,14-decamethyl-15,16-di(propan-2-yl)-15,16-diazapentacyclo[10.2.1.15,8.02,11.04,9]hexadeca-2(11),3,6,9,13-pentaene
  参考文献：
  名称：

  xxx作为多环axxx合成中的di-xxxxxx等价物

  摘要：

  1,2,4,5-四溴苯和类似的萘并萘烷与一或两当量的丁基锂和各种二烯（呋喃，吡咯，环戊二烯，富烯）反应形成单环或双环加合物。通过从呋喃或吡咯加合物中除去氧或氮桥，可以获得高度取代的芳烃。通过选择条件，可以将两个相同或两个不同的环稠合至二芳烃表位。描述了改进的全甲基萘，-蒽和-并四苯的短合成方法。提出了一种新的三苯撑合成。

  DOI：

  10.1016/s0040-4020(01)87696-1
• 作为产物：
  描述：

  3,4-二甲基-己烷-2,5-二酮 、 异丙胺 在 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 1-异丙基-2,3,4,5-四甲基-1H-吡咯
  参考文献：
  名称：

  Electrochemical Oxidation and EPR Spectroscopy of Radical Cations of N-Substituted 2,3,4,5-Tetramethylpyrroles.

  摘要：

  Electrochemical oxidation of 19 N-substituted 2,3,4,5-tetramethylpyrroles has been studied in acetonitrile and dichloromethane by means of slow cyclic voltammetry and coulometry. The first oxidation consumes one electron and occurs within the potential range 0.60-0.94 V in acetonitrile and 0.78-1.17 V in dichloromethane (vs. SCE). Twelve in situ generated primary radical cations were sufficiently stable al lowered temperature in dichloromethane for EPR measurement and showed well resolved HFS. The g-values (approximate to 2.0026) and the coupling constants of 2,5-methyls (a(H) approximate to 1.5 mT), 3,4-methyls (a(H) approximate to 0.35 mT), and of the pyrrole nitrogen (a(N) approximate to 0.42 mT) are very proximate for all 12 radical cations. It can be concluded, with support from quantum chemical calculations, that the odd electron is localised entirely on the pyrrole ring in the a(2) HOMO of the parent molecule. Despite the odd electron distribution, the stability of the radical cations depends on the particular substituent attached to the pyrrole nitrogen.

  DOI：

  10.3891/acta.chem.scand.52-0399

文献信息

• Intermediates in the Paal-Knorr synthesis of pyrroles
  作者：Venkataraman Amarnath、Douglas C. Anthony、Kalyani Amarnath、William M. Valentine、Lawrence A. Wetterau、Doyle G. Graham

  DOI：10.1021/jo00024a040

  日期：1991.11

  The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored. In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m). This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step. The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:03:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.
• HART, HAROLD;LAI, CHUNG-YIN;NWOKOGU, GODSON CHUKUEMEKA;SHAMOUILIAN, SHAMO+, TETRAHEDRON, 43,(1987) N 22, 5203-5224
  作者：HART, HAROLD、LAI, CHUNG-YIN、NWOKOGU, GODSON CHUKUEMEKA、SHAMOUILIAN, SHAMO+

  DOI：——

  日期：——
• METHOD OF TREATMENT OR PROPHYLAXIS OF INFLAMMATORY PAIN
  申请人：Smith Maree Therese

  公开号：US20100292159A1

  公开（公告）日：2010-11-18

  This invention discloses the use of angiotensin II receptor 2 (AT 2 receptor) antagonists for the treatment, prophylaxis, reversal and/or symptomatic relief of inflammatory pain, including hyperalgesia, thermal or mechanical allodynia, in vertebrate animals and particularly in human subjects. The AT 2 receptor antagonists may be provided alone or in combination with other compounds such as those that are useful in the control of inflammatory conditions.
• METHOD OF TREATMENT OR PROPHYLAXIS
  申请人：SMITH MAREE THERESE

  公开号：US20110318329A1

  公开（公告）日：2011-12-29

  The present invention is directed to methods and agents that are useful in the prevention and amelioration of signs and symptoms associated with neuropathic conditions. More particularly, the present invention discloses the use of angiotensin II receptor 2 (AT 2 receptor) antagonists for the treatment, prophylaxis, reversal and/or symptomatic relief of neuropathic pain, including mechanical hyperalgesia, thermal or mechanical allodynia, diabetic pain and entrapment pain, in vertebrate animals and particularly in human subjects. The AT 2 receptor antagonists may be provided alone or in combination with other compounds such as those that are useful in the control of neuropathic conditions.
• Method of Treatment or Prophylaxis
  申请人：SPINIFEX PHARMACEUTICALS PTY LTD

  公开号：US20130296350A1

  公开（公告）日：2013-11-07

  The present invention is directed to methods and agents that are useful in the prevention and amelioration of signs and symptoms associated with neuropathic conditions. More particularly, the present invention discloses the use of angiotensin II receptor 2 (AT 2 receptor) antagonists for the treatment, prophylaxis, reversal and/or symptomatic relief of neuropathic pain, including mechanical hyperalgesia, thermal or mechanical allodynia, diabetic pain and entrapment pain, in vertebrate animals and particularly in human subjects. The AT 2 receptor antagonists may be provided alone or in combination with other compounds such as those that are useful in the control of neuropathic conditions.