Pyren-4-carbonsaeure | 22245-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: Pyren-4-carbonsaeure
• 英文别名: 4-pyrenecarboxylic acid；Pyrene-4-carboxylic acid
• CAS: 22245-48-3
• 化学式: C₁₇H₁₀O₂
• 分子量: 246.265
• InChiKey: DQDBGGOQZVBKDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Pyren-4-carbonsaeure 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 芘-4-基甲醇
  参考文献：
  名称：

  对映选择性Rh催化叠氮化物-内炔环加成制备轴向手性1,2,3-三唑

  摘要：

  通过过渡金属催化的不对称叠氮化物-炔烃环加成，构建含有 1,2,3-三唑的手性骨架取得了重大进展；然而，它们中的大多数仅限于通过去对称化和动态/动态动力学拆分合成中心手性的末端炔烃。对映选择性过渡金属催化的叠氮化物-内炔环加成反应极为有限。此外，通过过渡金属催化的不对称叠氮化物-内-炔烃环加成构建具有挑战性的五元（杂）联芳基轴向手性分子仍处于探索阶段。在此，我们首先报告了轴向手性 1,4,5-三取代 1,2,3-三唑的阻转选择性和原子经济合成，直接作为具有挑战性的五元阻转异构体的核心手性单元，通过内部炔烃和叠氮化物的对映选择性Rh催化叠氮化物-炔烃环加成（E-RhAAC）。该反应表现出优异的官能团耐受性，在温和条件下以中等至优异的产率（高达 99% 产率）和通常高至优异的对映选择性（高达 99%）锻造各种 C–C 轴向手性 1,2,3-三唑ee) 以及特定的区域控制。密度泛函理论 (DFT)

  DOI：

  10.1021/jacs.2c01985
• 作为产物：
  描述：

  1-芘-4-基-乙酮 在 sodium hydroxide 、 溴 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以88%的产率得到Pyren-4-carbonsaeure
  参考文献：
  名称：

  Efficient oxidation of promutagenic hydroxymethylpyrenes by cDNA-expressed human alcohol dehydrogenase ADH2 and its inhibition by various agents

  摘要：

  Alkylated polycyclic aromatic hydrocarbons can be metabolically activated via benzylic hydroxylation and sulphation to electrophilically reactive esters. However, we previously found that the predominant biotransformation route for the hepatocarcinogen 1-hydro-xymethylpyrene (1-HMP) in the rat in vivo is the oxidation of the side chain by alcohol dehydrogenases (ADHs) and aldehyde dehydrogenases to the carboxylic acid. Inhibition of this pathway by ethanol (competing ADH substrate) or 4-methylpyrazole (ADH inhibitor) led to a dramatic increase in the 1-HMP-induced DNA adduct formation in rat tissues in the preceding study. In order to elucidate the role of individual ADHs in the metabolism of alkylated polycyclic aromatic hydrocarbons, we expressed the various members of the human ADH family in bacteria. Cytosolic preparations from bacteria expressing ADH2 clearly oxidized hydroxymethylpyrene isomers (1-, 2- and 4-HMP) with the highest rate. This form was purified to near homogeneity to perform detailed kinetic analyses. High catalytic efficiencies (V-max/K-m) were observed with HMPs. Thus, this value was 10,000-fold higher for 2-HMP than for the reference substrate, ethanol. The corresponding aldehydes were also efficiently reduced by ADH2. 4-Methylpyrazole inhibited the oxidation of the HMP isomers as well as the reverse reaction. Daidzein, cimetidine and the competing substrate ethanol were further compounds that inhibited the ADH2-mediated oxidative detoxification of 1-HMP. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2007.08.030

文献信息

• 신규의 트리아졸로티아디아졸 화합물, 이의 용도, 및 이를 포함한 유기발광소자
  申请人：KONGJU NATIONAL UNIVERSITY INDUSTRY-UNIVERSITY COOPERATION FOUNDATION 공주대학교 산학협력단(220040332376) BRN ▼307-82-06478

  公开号：KR20170004492A

  公开（公告）日：2017-01-11

  본 발명은 하기 화학식 1로 표시되는 트리아졸로티아디아졸 화합물(여기서, R은 치환 또는 비치환된 탄소수 10 ~ 25의 다환식 아릴기 또는 메탈로세닐기이다)에 관한 것이다. 본 발명의, R을 포함하는 신규의 트리아졸로티아디아졸 화합물은 적색에서 청색 영역의 넓은 파장범위를 가지는 우수한 발광 특성 및 열 안정성을 가짐으로써 발광소자 또는 염료감응태양전지와 같은 유기전자소자에서 발광층의 재료로써 유용하게 사용될 수 있다. [화학식 1]

  这是关于三唑硫二唑化合物的专利，具有广泛的红至蓝光区域发光特性和热稳定性，可用作有机电子器件中发光层的材料，如发光二极管或染料敏化太阳能电池。
• Photo-induced energy transfer relay of N-heterocyclic carbene catalysis: an asymmetric α-fluorination/isomerization cascade
  作者：Xinhang Jiang、En Li、Jiean Chen、Yong Huang

  DOI：10.1039/d0cc07264h

  日期：——

  transfer process that leads to selective access of chiral allylic fluorides with a cis-olefin geometry. In the absence of a photocatalyst or light, the reaction proceeds smoothly to give (E)-olefin products, while the (Z)-isomer can be obtained under photosensitizing conditions. Preliminary mechanistic experiments suggest that an energy transfer process might be operative.

  烯烃产物的几何构型通常由合成中的热力学控制来驱动。能够切换顺/反选择性的方法很少。最近，光敏方法已经成为完成该任务的有力工具。在此报告中，我们报告了N-杂环卡宾（NHC）结合的中间体通过光致能量转移过程的原位异构化，该过程导致具有顺式-烯烃几何形状的手性烯丙基氟化物的选择性进入。在没有光催化剂或光的情况下，反应平稳进行，得到（E）-烯烃产物，而（Z异构体可以在光敏条件下获得。初步的机械实验表明，能量传递过程可能有效。
• Evolving Fluorophores into Circularly Polarized Luminophores with a Chiral Naphthalene Tetramer: Proposal of Excimer Chirality Rule for Circularly Polarized Luminescence
  作者：Kazuto Takaishi、Kazuhiro Iwachido、Ryosuke Takehana、Masanobu Uchiyama、Tadashi Ema

  DOI：10.1021/jacs.9b02582

  日期：2019.4.17

  A versatile method for converting various fluorescent polycyclic aromatic hydrocarbons into circularly polarized luminescence (CPL) excimer dyes with high glum and ΦFL values is reported. This method involves the functionalization of a chiral quaternaphthyl with six fluorophores via ester linkages in the last step of the synthesis. The usefulness of this approach was demonstrated for 1-, 2-, and 4-pyrenyl

  报告了一种将各种荧光多环芳烃转化为具有高 glum 和 ΦFL 值的圆偏振发光 (CPL) 准分子染料的通用方法。该方法涉及在合成的最后一步通过酯键用六个荧光团对手性季萘进行功能化。这种方法对 1-、2- 和 4-芘基、2- 和 3- 苝基以及 2-蒽基染料的有效性得到了证明。它们中的大多数是 CPL 染料的第一个或罕见的例子。在基态，荧光团通过累积空间和电子效应紧密排列。在激发态，荧光团形成扭曲准分子，维持基态构象。局部手性准分子直接影响 CPL 性能。
• Tuning the mechanistic pathways of peptide self-assembly by aromatic interactions
  作者：Goutam Ghosh、Kalathil K. Kartha、Gustavo Fernández

  DOI：10.1039/d0cc07199d

  日期：——

  Herein, we have unravelled the key influence of aromatic interactions on the mechanistic pathways of peptide self-assembly by introducing suitable chromophores (pyrene vs. naphthalene). Although both self-assembled peptides are indistinguishable in their morphologies, this minor structural difference strongly affects the packing modes (parallel vs. antiparallel) and the corresponding self-assembly

  本文中，我们通过引入合适的生色团（py与萘），揭示了芳香族相互作用对肽自组装机理的关键影响。尽管两种自组装肽在形态上都无法区分，但是这种微小的结构差异会强烈影响包装模式（平行与反平行）和相应的自组装机制（合作与同构）。
• Orientational Control of Circularly Polarized Luminescence from Pyrene Clusters by Using a DNA Scaffold
  作者：Hiromu Kashida、Yuka Ito、Takahiro Kakuta、Tomoki Ogoshi、Hiroyuki Asanuma

  DOI：10.1002/chem.202300182

  日期：——

  Not just any which way: Circularly polarized luminescence from a pyrene cluster in DNA duplexes has been systematically investigated. CPL properties varied depending not only on the distance but also on the relative orientation between two pyrene dimers.

  不仅仅是任何方式：已经系统地研究了 DNA 双链体中芘簇的圆偏振发光。CPL 特性不仅取决于距离，还取决于两个芘二聚体之间的相对方向。