2,8-diethyl-1,3,5,7,9-pentamethyldipyrrin hydrochloride | 134370-64-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,8-diethyl-1,3,5,7,9-pentamethyldipyrrin hydrochloride
• CAS: 134370-64-2
• 化学式: C₁₈H₂₆N₂*ClH
• 分子量: 306.879
• InChiKey: SIXMKPALQJSSAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.15
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,8-diethyl-1,3,5,7,9-pentamethyldipyrrin hydrochloride 在 三乙胺 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 2.25h， 以89%的产率得到硼,[3-乙基-5-[1-(4-乙基-3,5-二甲基-2H-吡咯-2-亚基-kN)乙基]-2,4-二甲基-1H-吡咯酸根-kN]二氟-,(T-4)-
  参考文献：
  名称：

  Conversion of 4,4-Difluoro-4-bora-3a,4a-diaza-s-indacenes (F-BODIPYs) to Dipyrrins with a Microwave-Promoted Deprotection Strategy

  摘要：

  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.

  DOI：

  10.1021/ol902908j

文献信息

• Robust synthesis of F-BODIPYs
  作者：Michael Helmut Reynolds Beh、Katherine Isabelle Biehn Douglas、Kelsey Taylor Elver House、Alexandra Celeste Murphy、Jackson Scott Testemale Sinclair、Alison Thompson

  DOI：10.1039/c6ob02238c

  日期：——

  A protocol is established for the high-yielding synthesis of F-BODIPYs involving non-anhydrous reagents and not requiring precautions to exclude moisture.

  建立了一种用于高产率合成F-BODIPYs的协议，该协议涉及非无水试剂，并且不需要采取预防措施来排除湿气。
• 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.
• Perfluoroaryl-Substituted Boron Dipyrrinato Complexes
  作者：Catherine Bonnier、Warren E. Piers、Adeeb Al-Sheikh Ali、Alison Thompson、Masood Parvez

  DOI：10.1021/om900402e

  日期：2009.8.24

  A methodology for the incorporation of fluoroaryl groups into boron dipyrrinato complexes (modified BODIPY dyes) is reported. Two hexaalkylated dipyrrinato ligands with either H or CH3 occupying the meso position were employed; when they were treated with fluoroaryl haloboranes in the presence of a weak base, the title compounds were prepared in good to excellent yields. The structures of seven derivatives were determined using X-ray crystallography, and their spectroscopic, photophysical, and redox properties are compared.
• Silicon Compounds of 1,1-Bis(pyrrol-2-yl)ethenes: Molecular Structures and Chemical and Spectroscopic Properties
  作者：Alexander Kämpfe、Edwin Kroke、Jörg Wagler

  DOI：10.1021/om400868w

  日期：2014.1.13

  The first examples of silicon compounds of 1,1-bis(pyrrol-2-yl)ethenes have been synthesized via salt metathesis from a 2-fold lithiated dipyrromethene and different diorganodichlorosilanes (i.e., dimethyldichlorosilane, diphenyldichlorosilane, and 1,1-dichlorosilacyclobutane). Herein we report on their molecular structures, their optical properties, and some reactivity patterns.
• Formation of Vinylic Dipyrroles by the Deprotonation of <i>meso</i>-Alkyl and <i>meso</i>-Benzyl Dipyrrin HCl Salts
  作者：Adeeb Al-Sheikh Ali、Judy Cipot-Wechsler、T. Stanley Cameron、Alison Thompson

  DOI：10.1021/jo900064y

  日期：2009.4.3

  Under basic conditions, dipyrrin salts bearing alkyl and benzyl groups at the meso-position undergo deprotonation to give vinylic dipyrroles, rather than the corresponding free-base dipyrrins. The deprotonation is reversible and quantitatively returns the dipyrrinato framework under acidic conditions.