1-iodo-4-(4-methoxybenzyloxy)benzene | 682756-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-iodo-4-(4-methoxybenzyloxy)benzene
• 英文别名: 4-[(4-Methoxyphenyl)methoxy]iodobenzene；1-iodo-4-[(4-methoxyphenyl)methoxy]benzene
• CAS: 682756-44-1
• 化学式: C₁₄H₁₃IO₂
• 分子量: 340.161
• InChiKey: KQKBBQFDQSRXEA-UHFFFAOYSA-N

物化性质

• 沸点：
  398.5±27.0 °C(Predicted)
• 密度：
  1.544±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-iodo-4-(4-methoxybenzyloxy)benzene 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 正丁基锂 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 108.5h， 生成 (1E,3E,5E)-1-{4-[(4-methoxyphenyl)methoxy]phenyl}-6-phenylhexa-1,3,5-triene
  参考文献：
  名称：

  磷酸化的1,6-二苯基-1,3,5-己三烯。

  摘要：

  制备了由（1E，3E，5E）-1,6-二苯基-1,3,5-己三烯（DPH）荧光基团附着在磷酸二酯上构成的亲脂性染料，其在不同溶剂体系中和在检查脂质体膜双层。染料功能化末端合成的关键步骤是受保护的碘酚与炔丙醇的Sonogashira偶联；全反式多烯核的其余苯环和双键是由与反式肉桂醛的Wittig反应产生的。像DPH本身一样，其磷酸化衍生物的发射强度在极性介质中被猝灭。

  DOI：

  10.1016/j.bmcl.2004.01.005
• 作为产物：
  描述：

  4-碘苯酚 、 4-甲氧基溴苄 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以88.9%的产率得到1-iodo-4-(4-methoxybenzyloxy)benzene
  参考文献：
  名称：

  Radioiodinated Benzyloxybenzene Derivatives: A Class of Flexible Ligands Target to β-Amyloid Plaques in Alzheimer’s Brains

  摘要：

  Benzyloxybenzene, as a novel flexible scaffold without rigid planarity, was synthesized and evaluated as ligand toward A beta plaques. The binding site calculated for these flexible ligands was the hydrophobic Val18_Phe20 channel on the flat surface of A beta fiber. Structure activity relationship analysis generated a common trend that binding affinities declined significantly from para-substituted ligands to ortho-substituted ones, which was also quantitatively illustrated by 3D-QSAR modeling. Autoradiography in vitro further confirmed the high affinities of radioiodinated ligands [I-125]4, [I-125]24, and [I-125]22 (K-i = 24.3, 49.4, and 17.6 nM, respectively). In biodistribution, [I-125]4 exhibited high initial uptake and rapid washout property in the brain with brain(2 min)/brain(60 min) ratio of 16.3. The excellent in vitro and in vivo biostability of [I-125]4 enhanced its potential for clinical application in SPECT imaging of A beta plaques. This approach could also allow the design of a new generation of A beta targeting ligands without rigid and planar framework.

  DOI：

  10.1021/jm5004396

文献信息

• Copper‐Photocatalyzed Borylation of Organic Halides under Batch and Continuous‐Flow Conditions
  作者：Antoine Nitelet、Damien Thevenet、Bruno Schiavi、Christophe Hardouin、Jean Fournier、Rodolphe Tamion、Xavier Pannecoucke、Philippe Jubault、Thomas Poisson

  DOI：10.1002/chem.201806345

  日期：——

  The copper‐photocatalyzed borylation of aryl, heteroaryl, vinyl and alkyl halides (I and Br) was reported. The reaction proceeded using a new heteroleptic Cu complex under irradiation with blue LEDs, giving the corresponding boronic‐acid esters in good to excellent yields. The reaction was extended to continuous‐flow conditions to allow an easy scale‐up. The mechanism of the reaction was studied and

  据报道，铜光催化的芳基，杂芳基，乙烯基和烷基卤化物（I和Br）的硼化反应。该反应在蓝色LED的照射下使用一种新型的杂铜配合物进行，从而得到了相应的硼酸酯，收率良好至极佳。反应扩展到连续流动条件，以易于放大。研究了该反应的机理，并提出了基于还原淬灭（Cu I / Cu I * / Cu 0）的机理。
• PHENYL BENZYL ETHER DERIVATIVE AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：ZHANG Zhiyong

  公开号：US20170037008A1

  公开（公告）日：2017-02-09

  Parts of compounds, after being labeled by radionuclide, of the phenyl benzyl ether derivative, are used as Aβ plaque imaging agent. The structural formula of the phenyl benzyl ether derivative is shown by formula (I). The present invention develops a kind of brand new phenyl benzyl ether derivative which has high affinity with Aβ plaques in brains of AD patients. The chemical structure of the phenyl benzyl ether derivative is different from that of compounds disclosed in the prior art and the phenyl benzyl ether derivative belongs to a brand new compound for diagnosing and treating AD. The obtained Aβ plaque imaging agent has the advantages that the in-vivo stability is good, the fat solubility is low, the removal speed for the brain is fast, the problem of removing the radionuclide in vivo does not exist, and the application prospect and the market value are great.

  化合物的部分，在被放射性核素标记后，苯基苄醚衍生物被用作Aβ斑块成像剂。苯基苄醚衍生物的结构式如公式（I）所示。本发明开发了一种全新的苯基苄醚衍生物，其与AD患者大脑中的Aβ斑块具有高亲和力。苯基苄醚衍生物的化学结构与先前公开的化合物不同，且该苯基苄醚衍生物属于一种全新的用于诊断和治疗AD的化合物。所得的Aβ斑块成像剂具有优点，即体内稳定性好，脂溶性低，对大脑的清除速度快，不存在体内去除放射性核素的问题，且应用前景和市场价值巨大。
• Palladium-Catalyzed Base-Promoted Arylation of Unactivated C(sp³)-H Bonds by Aryl Iodides: A Practical Approach To Synthesize β-Aryl Carboxylic Acid Derivatives
  作者：Quan Gou、Gang Liu、Lanxiu Zhou、Suiyun Chen、Jun Qin

  DOI：10.1002/ejoc.201701215

  日期：2017.11.16

  A highly efficient protocol for the β-arylation of carboxylic amides by aryl iodides under PdCl2(CH3CN)2/CsOAc catalysis was developed. This method was found to tolerate a broad scope of substrates and was successfully employed in the preparation of a variety of β-aryl α-amino and γ-amino acid derivatives. The utility of this method was further illustrated in the synthesis of the psychotropic drug

  开发了一种高效的方案，用于在 PdCl2(CH3CN)2/CsOAc 催化下芳基碘化物对羧酰胺进行 β-芳基化。发现该方法可耐受广泛的底物，并成功用于制备各种 β-芳基 α-氨基和 γ-氨基酸衍生物。这种方法的效用在精神药物 (±)-phenibut 和 β-芳基胆汁酸类似物的合成中得到了进一步说明。
• SHP2抑制剂及其组合物和应用
  申请人：贝达药业股份有限公司

  公开号：CN115515947A

  公开（公告）日：2022-12-23

  本发明涉及一种作为含Src同源区2蛋白质酪氨酸磷酸酶2(SHP2)抑制剂的化合物(如式Ⅰ所示)，及其药物组合物、制备方法，以及其在治疗SHP2介导的疾病中的用途。本发明的化合物通过参与调节细胞增殖、凋亡、迁移、新生血管生成等多个过程而发挥作用。
• Radioiodinated Benzyloxybenzene Derivatives: A Class of Flexible Ligands Target to β-Amyloid Plaques in Alzheimer’s Brains
  作者：Yanping Yang、Mengchao Cui、Xiaoyang Zhang、Jiapei Dai、Zhiyong Zhang、Chunping Lin、Yuzhi Guo、Boli Liu

  DOI：10.1021/jm5004396

  日期：2014.7.24

  Benzyloxybenzene, as a novel flexible scaffold without rigid planarity, was synthesized and evaluated as ligand toward A beta plaques. The binding site calculated for these flexible ligands was the hydrophobic Val18_Phe20 channel on the flat surface of A beta fiber. Structure activity relationship analysis generated a common trend that binding affinities declined significantly from para-substituted ligands to ortho-substituted ones, which was also quantitatively illustrated by 3D-QSAR modeling. Autoradiography in vitro further confirmed the high affinities of radioiodinated ligands [I-125]4, [I-125]24, and [I-125]22 (K-i = 24.3, 49.4, and 17.6 nM, respectively). In biodistribution, [I-125]4 exhibited high initial uptake and rapid washout property in the brain with brain(2 min)/brain(60 min) ratio of 16.3. The excellent in vitro and in vivo biostability of [I-125]4 enhanced its potential for clinical application in SPECT imaging of A beta plaques. This approach could also allow the design of a new generation of A beta targeting ligands without rigid and planar framework.