5-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dipyrromethane | 389799-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dipyrromethane
• 英文别名: 2-[1H-pyrrol-2-yl-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]-1H-pyrrole
• CAS: 389799-72-8
• 化学式: C₂₁H₂₅BN₂O₂
• 分子量: 348.253
• InChiKey: USFNUJSTDMBUDT-UHFFFAOYSA-N

物化性质

• 沸点：
  523.9±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dipyrromethane 在 盐酸 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 13.75h， 生成 5,15-bis(4-dioxylborylphenyl)porphyrin
  参考文献：
  名称：

  Design and studies of novel polyoxysterol-based porphyrin conjugates

  摘要：

  New types of steroid-porphyrin conjugates derived from 20-hydroxyecdysone (20E) and 24-epibrassinolide (EBI) were synthesized. An exceptional regioselectivity in the reaction of both steroids with porphyrin boronic acids was found to give side-chain-conjugated boronic esters as sole products. UV-Vis-, fluorescence and NMR spectroscopy yielded similar data for all the studied compounds confirming the solvent driven supramolecular assembly with formation of J-aggregates. CD measurements of water diluted solutions showed a clear difference between 20E and EBI conjugates. The latter showed a strong supramolecular chirality, whereas 20E J-aggregates did not. (C) 2012 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2012.07.005
• 作为产物：
  描述：

  4-甲酰基苯硼酸 在 三氟乙酸 作用下， 以 乙醚 为溶剂， 反应 15.08h， 生成 5-[4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dipyrromethane
  参考文献：
  名称：

  Investigation of two rational routes for preparing p-phenylene-linked porphyrin trimers

  摘要：

  Multiporphyrin arrays with p-phenylene linkers, aryl groups at the non-linking meso positions, and no beta -substiments are attractive constructs for light-harvesting applications. Condensation of a free base porphyrin-benzaldehyde and 5-mesityldipyrromethane (10 mM each) in CH2Cl2 containing 100 mM TFA at room temperature for 30-40 min followed by oxidation with DDQ afforded a p-phenylene-linked porphyrin trimer in 36% yield. Suzuki coupling of an iodo-porphyrin and a bis(dioxaborolane)-porphyrin (20 and 10 mM, respectively) in toluene/DMF (2:1) containing K2CO3 (8 equiv.) at 90-95 degreesC for similar to 20 h afforded the same trimer in 66% yield. The former route was used to prepare a diethynyl substituted p-phenylene-linked porphyrin trimer. While the two routes are somewhat complementary in scope, both are convergent and proceed in a rational manner. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00928-0

文献信息

• Methods and intermediates for the synthesis of dipyrrin-substituted porphyrinic macrocycles
  申请人：——

  公开号：US20040254383A1

  公开（公告）日：2004-12-16

  The present invention provides dipyrrin substituted porphyrinic macrocycles, intermediates useful for making the same, and methods of making the same. Such compounds may be used for purposes including the making of molecular memory devices, solar cells and light harvesting arrays.

  本发明提供了取代二吡啶基卟啉宏环、制备相同化合物有用的中间体，以及制备相同化合物的方法。这些化合物可用于制造分子存储设备、太阳能电池和光收集阵列等用途。
• Excited-State Energy-Transfer Dynamics in Self-Assembled Triads Composed of Two Porphyrins and an Intervening Bis(dipyrrinato)metal Complex
  作者：Lianhe Yu、Kannan Muthukumaran、Igor V. Sazanovich、Christine Kirmaier、Eve Hindin、James R. Diers、Paul D. Boyle、David F. Bocian、Dewey Holten、Jonathan S. Lindsey

  DOI：10.1021/ic034559m

  日期：2003.10.1

  synthesis and characterization of various triads composed of a linear array of two zinc porphyrins joined via an intervening bis(dipyrrinato)metal(II) complex are reported. The preparation exploits the facile complexation of dipyrrins with divalent metal ions to give bis(dipyrrinato)metal(II) complexes [abbreviated (dp)(2)M]. Copper(II) and palladium(II) chelates of dipyrrins (available by oxidation

  报道了由三元锌卟啉的线性阵列组成的各种三联体的合成和表征，所述二元锌卟啉通过中间双（dipyrrinato）金属（II）配合物连接。该制备方法利用双吡啶与二价金属离子的简易络合生成双（dipyrrinato）金属（II）络合物[缩写为（dp）（2）M]。以50-80％的收率制备二吡喃铜（II）和钯（II）螯合物（可通过二吡咯甲烷的氧化获得）。在Zn（OAc）（2）.2H（2）O在THF中（约80 ％ 屈服）。开发了制备卟啉-联吡啶的三种途径：（1）。硼酸酯取代的卟啉锌（ZnP）和双[5-（4-碘苯基）二吡喃酮对] Pd（II）的Suzuki偶联，得到（ZnP-dp）（2）Pd三元组（50％收率），然后进行选择性（dp）（2）Pd单元通过在中性条件下用1,4-二硫苏糖醇处理进行脱金属（71％收率）; （2）。在Zn（OAc）（2）.2H（2）O存在下，用对氯苯胺氧化卟啉-二吡咯甲烷，然后在硅
• [EN] PORPHYRIN-HYDROPORPHYRIN COMPOUNDS, COMPOSITIONS COMPRISING THE SAME AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS DE PORPHYRINE-HYDROPORPHYRINE, COMPOSITIONS LES COMPRENANT ET LEURS PROCÉDÉS D'UTILISATION
  申请人：[en]NORTH CAROLINA STATE UNIVERSITY

  公开号：WO2022216927A1

  公开（公告）日：2022-10-13

  Described herein are compounds that include a first porphyrin; and a first hydroporphyrin, wherein the first porphyrin is attached to the first hydroporphyrin. The compound may be a luminescent compound (e.g., a fluorescent compound). Also provided are particles and compositions including compounds described herein. Further provided are methods of making and using the particles and methods of making the same.
• Investigation of two rational routes for preparing p-phenylene-linked porphyrin trimers
  作者：Lianhe Yu、Jonathan S Lindsey

  DOI：10.1016/s0040-4020(01)00928-0

  日期：2001.11

  Multiporphyrin arrays with p-phenylene linkers, aryl groups at the non-linking meso positions, and no beta -substiments are attractive constructs for light-harvesting applications. Condensation of a free base porphyrin-benzaldehyde and 5-mesityldipyrromethane (10 mM each) in CH2Cl2 containing 100 mM TFA at room temperature for 30-40 min followed by oxidation with DDQ afforded a p-phenylene-linked porphyrin trimer in 36% yield. Suzuki coupling of an iodo-porphyrin and a bis(dioxaborolane)-porphyrin (20 and 10 mM, respectively) in toluene/DMF (2:1) containing K2CO3 (8 equiv.) at 90-95 degreesC for similar to 20 h afforded the same trimer in 66% yield. The former route was used to prepare a diethynyl substituted p-phenylene-linked porphyrin trimer. While the two routes are somewhat complementary in scope, both are convergent and proceed in a rational manner. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Design and studies of novel polyoxysterol-based porphyrin conjugates
  作者：Halina A. Zhylitskaya、Vladimir N. Zhabinskii、Raisa P. Litvinovskaya、Raffaella Lettieri、Donato Monti、Mariano Venanzi、Vladimir A. Khripach、Pavel Drašar

  DOI：10.1016/j.steroids.2012.07.005

  日期：2012.9

  New types of steroid-porphyrin conjugates derived from 20-hydroxyecdysone (20E) and 24-epibrassinolide (EBI) were synthesized. An exceptional regioselectivity in the reaction of both steroids with porphyrin boronic acids was found to give side-chain-conjugated boronic esters as sole products. UV-Vis-, fluorescence and NMR spectroscopy yielded similar data for all the studied compounds confirming the solvent driven supramolecular assembly with formation of J-aggregates. CD measurements of water diluted solutions showed a clear difference between 20E and EBI conjugates. The latter showed a strong supramolecular chirality, whereas 20E J-aggregates did not. (C) 2012 Elsevier Inc. All rights reserved.