<4-N-(acetylamino)benzyl>triphenylphosphonium bromide | 139656-15-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: <4-N-(acetylamino)benzyl>triphenylphosphonium bromide
• 英文别名: [4-(N-acetylamino)benzyltriphenyl]phosphonium bromide；(4-acetamidobenzyl)triphenylphosphonium bromide；[4-N-(acetylamino)benzyl]triphenylphosphonium bromide；N-[4-(triphenylphosphaniumylmethyl)phenyl]ethanimidate;hydrobromide
• CAS: 139656-15-8
• 化学式: Br*C₂₇H₂₅NOP
• 分子量: 490.379
• InChiKey: RINOVWIVCNBHQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  <4-N-(acetylamino)benzyl>triphenylphosphonium bromide 在 吡啶 、 氢氧化钾 、 sodium methylate 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 11.5h， 生成 N-{4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-Tetramethyl-18-(2,6,6-trimethyl-cyclohex-1-enyl)-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-phenyl}-4-((1Z,4Z,9Z,15Z)-10,15,20-tri-p-tolyl-porphyrin-5-yl)-benzamide
  参考文献：
  名称：

  胡萝卜素-卟啉二元组中的三重态和单重态能量转移：连接键的作用。

  摘要：

  已经制备了一系列类胡萝卜素二元分子，其中类胡萝卜素在中间芳香环的邻位、间位或对位共价连接到四芳基卟啉，并使用稳态和瞬态荧光发射、瞬态荧光对这些分子进行了研究。吸收和 1 H NMR 方法。已经观察到从卟啉部分到类胡萝卜素的三线态能量转移，以及从类胡萝卜素多烯到卟啉的单线态能量转移

  DOI：

  10.1021/ja00036a002
• 作为产物：
  描述：

  对氨基苯甲醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 <4-N-(acetylamino)benzyl>triphenylphosphonium bromide
  参考文献：
  名称：

  供体 - 受体侧翼记者二苯乙烯的温和化学和生物合成：生理 Wittig 烯烃化反应的证明

  摘要：

  据报道，Wittig 烯化反应具有前所未有的化学选择性，导致在生理条件下形成报道二苯乙烯。

  DOI：

  10.1002/ejoc.201201042

文献信息

• Carotenoid Photoprotection in Artificial Photosynthetic Antennas
  作者：Miroslav Kloz、Smitha Pillai、Gerdenis Kodis、Devens Gust、Thomas A. Moore、Ana L. Moore、Rienk van Grondelle、John T. M. Kennis

  DOI：10.1021/ja1103553

  日期：2011.5.11

  A series of phthalocyanine carotenoid dyads in which a phenylamino group links a phthalocyanine to carotenoids having 8-11 backbone double bonds were examined by visible and near-infrared femtosecond pump-probe spectroscopy combined with global fitting analysis. The series of molecules has permitted investigation of the role of carotenoids in the quenching of excited states of cyclic tetrapyrroles. The transient behavior varied dramatically with the length of the carotenoid and the solvent environment. Clear spectroscopic signatures of radical species revealed photoinduced electron transfer as the main quenching mechanism for all dyads dissolved in a polar solvent (THF), and the quenching rate was almost independent of carotenoid length. However, in a nonpolar solvent (toluene), quenching rates displayed a strong dependence on the conjugation length of the carotenoid and the mechanism did not include charge separation. The lack of any rise time components of a carotenoid S-1 signature in all experiments in toluene suggests that an excitonic coupling between the carotenoid S-1 state and phthalocyanine Q state, rather than a conventional energy transfer process, is the major mechanism of quenching. A pronounced inhomogeneity of the system was observed and attributed to the presence of a phenyl-amino linker between phthalocyanine and carotenoids. On the basis of accumulated work on various caroteno phthalocyanine dyads and triads, we have now identified three mechanisms of tetrapyrrole singlet excited state quenching by carotenoids in artificial systems: (i) Car Pc electron transfer and recombination; (ii)(1) Pc to Car S-1 energy transfer and fast internal conversion to the Car ground state; (iii) excitonic coupling between Pc-1 and Car S-1 and ensuing internal conversion to the ground state of the carotenoid. The dominant mechanism depends upon the exact molecular architecture and solvent environment. These synthetic systems are providing a deeper understanding of structural and environmental effects on the interactions between carotenoids and tetrapyrroles and thereby better defining their role in controlling natural photosynthetic systems.
• THE USE OF CAROTENOPORPHYRINS AS TUMOR LOCALIZING AGENTS FOR DIAGNOSIS, VISUALIZATION AND DELIVERY OF SENSITIZERS TO TUMOR TISSUES
  申请人：ARIZONA BOARD OF REGENTS

  公开号：EP0626866A1

  公开（公告）日：1994-12-07
• EP0626866A4
  申请人：——

  公开号：EP0626866A4

  公开（公告）日：1994-12-21
• US5286474A
  申请人：——

  公开号：US5286474A

  公开（公告）日：1994-02-15
• [EN] THE USE OF CAROTENOPORPHYRINS AS TUMOR LOCALIZING AGENTS FOR DIAGNOSIS, VISUALIZATION AND DELIVERY OF SENSITIZERS TO TUMOR TISSUES<br/>[FR] UTILISATION DE CAROTENOPORPHYRINES COMME AGENTS DE LOCALISATION DE TUMEURS DANS LE DIAGNOSTIC ET LA VISUALISATION DES TISSUS TUMORAUX, ET DANS L'ADMINISTRATION DE SENSIBILISANTS A CES TISSUS
  申请人：ARIZONA BOARD OF REGENTS

  公开号：WO1994008631A1

  公开（公告）日：1994-04-28

  (EN) A process of tumor identification comprising administering a carotenoporphyrin to a tumor-bearing mammalian host and irradiating the mammalian host with light whereupon the carotenoporphyrin, which has been preferentially taken up by the tumor tissue, fluoresces and permits precise identification of the location, size and shape of the tumor tissue. An improved process of synthesizing carotenoporphyrins 1-5 is also provided.(FR) Procédé d'identification de tumeurs consistant à administrer une caroténoporphyrine à un hôte mammifère atteint d'une tumeur, et à éclairer l'hôte mammifère de manière que la caroténoporphyrine, de préférence absorbée par le tissu tumoral, devienne fluorescente, et qu'elle permette une identification précise de l'emplacement, de la taille et de la forme du tissu tumoral. On a également prévu un procédé amélioré de synthèse des caroténoporphyrines 1 à 5.