(2Z)-4-乙基-2-[(4-乙基-3,5-二甲基-1H-吡咯-2-基)亚甲基]-3,5-二甲基吡咯 | 2407-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: (2Z)-4-乙基-2-[(4-乙基-3,5-二甲基-1H-吡咯-2-基)亚甲基]-3,5-二甲基吡咯
• 英文名称: (Z)-3-ethyl-5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)-methyl)-2,4-dimethyl-1H-pyrrole
• 英文别名: (Z)-3-ethyl-5-((4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene)methyl)-2,4-dimethyl-1H-pyrrole；4,4'-diethyl-3,3',5,5'-tetramethyldipyrrolylmethene；4,4'-diethyl-3,5,3',5'-tetramethyl-1H,2'H-2,2'-methanylylidene-bis-pyrrole；4,4'-Diaethyl-3,5,3',5'-tetramethyl-2,2'-dipyrrylmethen；3,3',5,5'-Tetramethyl-4,4'-diethyldipyrromethen；4,4'-Diethyl-3,5,3',5'-tetramethyldipyrromethen；(2Z)-4-ethyl-2-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylene]-3,5-dimethyl-pyrrole；(2Z)-4-ethyl-2-[(4-ethyl-3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-3,5-dimethylpyrrole
• CAS: 2407-83-2
• 化学式: C₁₇H₂₄N₂
• 分子量: 256.391
• InChiKey: QSPGBUOFJNDGBP-MFOYZWKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2Z)-4-乙基-2-[(4-乙基-3,5-二甲基-1H-吡咯-2-基)亚甲基]-3,5-二甲基吡咯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到lithium;(2Z)-4-ethyl-2-[(4-ethyl-3,5-dimethylpyrrol-1-id-2-yl)methylidene]-3,5-dimethylpyrrole
  参考文献：
  名称：

  The first series of alkali dipyrrinato complexes

  摘要：

  报告了第一个碱二吡咯烷酮配合物系列，包括中位未取代和中位芳基取代衍生物的锂、钠和钾盐。通过改变中位取代基，两个氮原子之间的分子间距发生了变化，从而改变了κ2-N,N-二齿咬合角，这一点通过比较二吡咯啉游离基在固态下的晶体结构得到了证实。成键模式随金属离子的离子半径增大而变化：固态结构显示锂被容纳在二吡咯烷单元的平面内，而钠则被容纳在平面外。类似的锂、钠和钾二吡咯烷酮络合物的反应性随着金属离子的离子半径的增加而增加，这与络合物的离子性随着碱金属尺寸的增加而增加这一概念是一致的。

  DOI：

  10.1139/v09-180
• 作为产物：
  描述：

  1,3,7,9-tetramethyl-2,8-diethyl-4,6-dipyrrin hydrobromide 在 水 、 三乙胺 、 potassium hydroxide 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 生成 (2Z)-4-乙基-2-[(4-乙基-3,5-二甲基-1H-吡咯-2-基)亚甲基]-3,5-二甲基吡咯
  参考文献：
  名称：

  Use of F-BODIPYs as a Protection Strategy for Dipyrrins: Optimization of BF₂ Removal

  摘要：

  We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of the corresponding free-base dipyrrin. Further optimization of the reaction has resulted in a more convenient and accessible protocol. The availability of this new methodology enables BF2-complexation to be used as a dipyrrin protection strategy. Herein lies a detailed examination of the deprotection reaction, with a view to optimization and gaining mechanistic insight, and its application in facilitating a multistep synthesis of pyrrolyldipyrrins.

  DOI：

  10.1021/jo3002003

文献信息

• Conversion of 4,4-Difluoro-4-bora-3a,4a-diaza-<i>s</i>-indacenes <b>(</b><i>F</i>-BODIPYs) to Dipyrrins with a Microwave-Promoted Deprotection Strategy
  作者：Sarah M. Crawford、Alison Thompson

  DOI：10.1021/ol902908j

  日期：2010.4.2

  4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) have been deprotected to give the corresponding free-base dipyrrins by heating a solution of the F-BODIPY In tert-butanol under 600 W of microwave irradiation in the presence of 6 equiv of potassium tert-butoxide for 40 min at 92 degrees C. Investigations of BODIPY modification at the meso position have also been undertaken and a meso-butyl product has been isolated.
• Use of <i>F</i>-BODIPYs as a Protection Strategy for Dipyrrins: Optimization of BF₂ Removal
  作者：Deborah A. Smithen、Alexander E. G. Baker、Matthew Offman、Sarah M. Crawford、T. Stanley Cameron、Alison Thompson

  DOI：10.1021/jo3002003

  日期：2012.4.6

  We recently reported the first general method for the deprotection of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) involving a microwave-assisted procedure for the removal of the BF2 moiety, and liberation of the corresponding free-base dipyrrin. Further optimization of the reaction has resulted in a more convenient and accessible protocol. The availability of this new methodology enables BF2-complexation to be used as a dipyrrin protection strategy. Herein lies a detailed examination of the deprotection reaction, with a view to optimization and gaining mechanistic insight, and its application in facilitating a multistep synthesis of pyrrolyldipyrrins.
• The first series of alkali dipyrrinato complexes
  作者：Adeeb Al-Sheikh Ali、Judy Cipot-Wechsler、Sarah M. Crawford、Omar Selim、Rhonda L. Stoddard、T. Stanley Cameron、Alison Thompson

  DOI：10.1139/v09-180

  日期：2010.8

  The first series of alkali dipyrrinato complexes is reported, encompassing lithium, sodium, and potassium salts of meso-unsubstituted and meso-aryl-substituted derivatives. By varying the substituents at the meso position, the intermolecular distance between the two nitrogen atoms and thus the κ²-N,N-bidentate bite angle was altered, as confirmed by comparison of crystallographic structures of dipyrrin free-bases in the solid-state. The mode of bonding varies as the ionic radius of the metal ion increases: solid-state structures reveal lithium to be accommodated in the plane of the dipyrrinato unit, whilst sodium is accommodated out of plane. The reactivity of analogous lithium, sodium, and potassium dipyrrinato complexes increases as the ionic radius of the metal ion increases, in keeping with the concept that the complexes tend towards an increasingly ionic nature as the size of the alkali metal increases.

  报告了第一个碱二吡咯烷酮配合物系列，包括中位未取代和中位芳基取代衍生物的锂、钠和钾盐。通过改变中位取代基，两个氮原子之间的分子间距发生了变化，从而改变了κ2-N,N-二齿咬合角，这一点通过比较二吡咯啉游离基在固态下的晶体结构得到了证实。成键模式随金属离子的离子半径增大而变化：固态结构显示锂被容纳在二吡咯烷单元的平面内，而钠则被容纳在平面外。类似的锂、钠和钾二吡咯烷酮络合物的反应性随着金属离子的离子半径的增加而增加，这与络合物的离子性随着碱金属尺寸的增加而增加这一概念是一致的。