1-iodo-4-(phenoxymethyl)benzene | 91718-22-8

• 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-(phenoxymethyl)benzene
• CAS: 91718-22-8
• 化学式: C₁₃H₁₁IO
• 分子量: 310.134
• InChiKey: YJHGKSUSTGKZQF-UHFFFAOYSA-N

物化性质

• 沸点：
  177-178 °C(Press: 2 Torr)
• 密度：
  1.580±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-iodo-4-(phenoxymethyl)benzene 在 NiCl₂(H₂O)6 吡啶 、 sodium hydroxide 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 56.25h， 生成 3-(4-(phenoxymethyl)phenyl)propanoic acid
  参考文献：
  名称：

  Structure−Activity Relationships of α-Ketooxazole Inhibitors of Fatty Acid Amide Hydrolase

  摘要：

  A systematic study of the structure-activity relationships of 2b (OL-135), a potent inhibitor of fatty acid amide hydrolase (FAAH), is detailed targeting the C2 acyl side chain. A series of aryl replacements or substituents for the terminal phenyl group provided effective inhibitors (e.g., 5c, aryl = 1- napthyl, K-i = 2.6 nM), with 5hh (aryl = 3-ClPh, K-i = 900 pM) being 5-fold more potent than 2b. Conformationally restricted C2 side chains were examined, and many provided exceptionally potent inhibitors, of which 11j (ethylbiphenyl side chain) was established to be a 750 pM inhibitor. A systematic series of heteroatoms (O, NMe, S), electron-withdrawing groups (SO, SO2), and amides positioned within and hydroxyl substitutions on the linking side chain were investigated, which typically led to a loss in potency. The most tolerant positions provided effective inhibitors (12p, 6-position S, K-i = 3 nM, or 13d, 2-position OH, K-i = 8 nM) comparable in potency to 2b. Proteome-wide screening of selected inhibitors from the systematic series of > 100 candidates prepared revealed that they are selective for FAAH over all other mammalian serine proteases.

  DOI：

  10.1021/jm061414r
• 作为产物：
  描述：

  (benzyloxy)benzene 在 aluminum oxide 、 过碘酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以40%的产率得到1-iodo-4-(phenoxymethyl)benzene
  参考文献：
  名称：

  HIO 4 / Al 2 O 3作为用于活化芳族化合物和1,3-二羰基化合物加碘的新系统

  摘要：

  描述了将高碘酸/氧化铝体系用于活化的芳族化合物和1，3-二羰基化合物的碘化的用途。

  DOI：

  10.1016/j.tetlet.2006.03.102

文献信息

• Base‐Mediated O‐Arylation of Alcohols and Phenols by Triarylsulfonium Triflates
  作者：Xiao‐Xia Ming、Ze‐Yu Tian、Cheng‐Pan Zhang

  DOI：10.1002/asia.201900968

  日期：2019.10

  A mild and efficient protocol for O-arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition-metal-free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron-donating or electron-withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent

  在不含过渡金属的条件下，开发了温和有效的三芳基ulf三氟甲磺酸酯进行醇和酚（ROH）芳基化的方案。各种醇，包括在芳基环上带有给电子或吸电子基团的伯，仲和叔醇以及苯酚，可以平稳转化为相应的芳族醚，产率中等至优异。反应在一定的碱存在下于50或80°C进行24小时，并显示出良好的官能团耐受性。不对称的三芳基ulf盐的碱介导的芳基化反应可以选择性地将sulf的芳基转移到ROH上，具体取决于它们固有的电子性质。
• Catalytic Aerobic Synthesis of Aromatic Ethers from Non-Aromatic Precursors
  作者：Marc-Olivier Simon、Simon A. Girard、Chao-Jun Li

  DOI：10.1002/anie.201200698

  日期：2012.7.23

  Only little waste: Aryl ether formation is accomplished by oxidative condensation of alcohols and 2‐cyclohexenones. The reaction complements the existing methods used by synthetic chemists to obtain aryl ethers, and allows a straightforward access to a wide range of functionalized products. In addition, the catalytic reaction with O2 as the oxidant generates water as the only by‐product and provides

  只有很少的浪费：芳基醚的形成是通过醇和2-环己烯酮的氧化缩合完成的。该反应是合成化学家用于获得芳基醚的现有方法的补充，并允许直接获得各种功能化的产物。此外，以O 2为氧化剂的催化反应生成水作为唯一的副产物，并为芳基醚提供了“更绿色”的方法。
• 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。
• Ring Opening of Pymisyl‐Protected Aziridines with Organocuprates
  作者：Jan Bornholdt、Jakob Felding、Rasmus P. Clausen、Jesper L. Kristensen

  DOI：10.1002/chem.201001026

  日期：2010.11.2

  The pyrimidine‐2‐sulfonyl (pymisyl) group is introduced as a new protecting group that can be used to activate aziridines towards ring opening. It is readily introduced and removed under mild conditions. Regioselective ring opening of pymisyl‐protected 2‐methyl‐aziridine with organocuprates gives the corresponding sulfonamides in high yields, and the pymisyl group can subsequently be removed upon treatment

  引入了嘧啶-2-磺酰基（嘧啶基）作为新的保护基，可用于激活氮丙啶向开环的方向移动。它很容易在温和的条件下引入和除去。嘧啶保护的2-甲基氮丙啶与有机铜的区域选择性开环可得到高产率的相应磺酰胺，随后可在用硫醇盐处理后除去嘧啶基。这种新的氮保护基团的多功能性可以通过新合成的司来吉兰（一种用于治疗帕金森氏病的单胺氧化酶-B抑制剂）的合成来说明。
• Deep Eutectic Solvent Compatible Metallic Catalysts: Cationic Pyridiniophosphine Ligands in Palladium Catalyzed Cross-Coupling Reactions
  作者：Xavier Marset、Abbas Khoshnood、Lia Sotorríos、Enrique Gómez-Bengoa、Diego A. Alonso、Diego J. Ramón

  DOI：10.1002/cctc.201601544

  日期：2017.4.7

  combination with PdCl2, have been successfully applied to different palladium‐catalyzed cross coupling reactions, such as Suzuki–Miyaura, Sonogashira, or Heck couplings. While traditional palladium ligands in DES medium failed to reproduce the results obtained in VOC solvents, these cationic phosphines improved the catalytic activity of palladium as no other traditional ligand could in such a polar medium

  阳离子吡啶碘膦配体已经合成，以尝试开发与低共熔溶剂（DESs）兼容的催化体系。这些配体与PdCl 2结合，已成功应用于各种钯催化的交叉偶联反应，例如Suzuki–Miyaura，Sonogashira或Heck偶联。尽管DES介质中的传统钯配体无法重现在VOC溶剂中获得的结果，但这些阳离子膦却改善了钯的催化活性，这是其他传统配体无法在这种极性介质中实现的。此外，还研究了这些工艺的可回收性，使我们在铃木和Sonogashira反应中最多可重复使用5次催化剂和溶剂，而催化活性却没有显着下降。关于Pd催化剂的结构，滴定，NMR和DFT研究已经清楚地证明了DES相容性阳离子膦配体的配位性能。