3-碘-4-苯氧基苯甲酸甲酯 | 100725-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-碘-4-苯氧基苯甲酸甲酯
• 英文名称: 3-iodo-4-phenoxybenzoic acid methyl ester
• 英文别名: methyl 3-iodo-4-phenoxybenzoate；3-iodo-4-phenoxy-benzoic acid methyl ester；3-Jod-4-phenoxy-benzoesaeure-methylester
• CAS: 100725-29-9
• 化学式: C₁₄H₁₁IO₃
• mdl: MFCD02912489
• 分子量: 354.144
• InChiKey: GVEOVGCAYLUZEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  57 °C
• 沸点：
  387.1±37.0 °C(Predicted)
• 密度：
  1.609±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P261,P272,P280,P302+P352,P333+P313,P363,P501
• 危险性描述：
  H317

反应信息

• 作为反应物：
  描述：

  3-碘-4-苯氧基苯甲酸甲酯 在 palladium 10% on activated carbon 、 sodium acetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 16.0h， 以94%的产率得到methyl dibenzo[b,d]furan-2-carboxylate
  参考文献：
  名称：

  通过邻位碘代二芳基醚的C–H活化合成二苯并呋喃

  摘要：

  已经开发了一种在无配体条件下使用可重复使用的Pd / C由邻碘二芳基醚合成二苯并呋喃的有效方法。在温和的反应条件下，通过顺序碘化和苯酚的邻芳基化，可以在一锅中完成邻碘二芳基醚的合成。

  DOI：

  10.1021/acs.joc.5b00634
• 作为产物：
  描述：

  (5-(methoxycarbonyl)-2-(((trifluoromethyl)sulfonyl)oxy)phenyl)(phenyl)iodonium trifluoromethanesulfonate 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以85%的产率得到3-碘-4-苯氧基苯甲酸甲酯
  参考文献：
  名称：

  Diaryliodonium盐的分子内芳基迁移：获得邻碘二芳基醚的途径

  摘要：

  通过使用邻位的三氟甲磺酸取代的二芳基碘鎓盐，开发了一种通过分子内芳基迁移合成邻碘二芳基醚的新方法。反应条件温和，底物范围广。机械学的见解表明了磺酰基定向的亲核芳族取代途径。另外，产物邻碘二芳基醚可作为通用合成子，已通过数个偶联反应得到证明。此外，通过这种芳基迁移步骤合成了3-碘-1-甲状腺素（3-T 1）衍生物的有用的甲状腺素类似物。

  DOI：

  10.1002/anie.201806405

文献信息

• Synthesis of Dibenzofurans via C–H Activation of <i>o</i>-Iodo Diaryl Ethers
  作者：Niranjan Panda、Irshad Mattan、Dinesh Kumar Nayak

  DOI：10.1021/acs.joc.5b00634

  日期：2015.7.2

  An efficient method for the synthesis of dibenzofuran from o-iododiaryl ether using reusable Pd/C under ligand-free conditions has been developed. Synthesis of o-iododiaryl ether was achieved in one pot through sequential iodination and O-arylation of phenol under mild reaction conditions.

  已经开发了一种在无配体条件下使用可重复使用的Pd / C由邻碘二芳基醚合成二苯并呋喃的有效方法。在温和的反应条件下，通过顺序碘化和苯酚的邻芳基化，可以在一锅中完成邻碘二芳基醚的合成。
• Synthesis of medium-sized (6–7–6) ring compounds by iron-catalyzed dehydrogenative C–H activation/annulation
  作者：Niranjan Panda、Irshad Mattan、Subhadra Ojha、Chandra Shekhar Purohit

  DOI：10.1039/c8ob01496e

  日期：——

  afford a series of biologically potent fused seven-membered (6–7–6) ring compounds under mild reaction conditions. This reaction was believed to proceed through Friedel–Crafts type sequential carbometallation followed by protonation to produce phenyldibenz[b,f]oxepines. This method was also extended to synthesize seven-membered rings that are fused with coumarins.

  在本报告中，我们描述了FeCl 3催化的过程，该过程涉及通过氢芳基化作用使邻苯氧二芳基乙炔分子内环化，从而在温和的反应条件下提供一系列具有生物活性的稠合七元（6-7-6）环化合物。该反应被认为是通过Friedel-Crafts型连续碳金属化反应进行的，然后进行质子化反应生成苯基二苯并[ b，f ]氧杂环丁烷。该方法还扩展到合成与香豆素融合的七元环。
• One-pot syntheses of 2,6-diiododiaryl ethers from para-EWG-substituted phenols by diacetoxyiodobenzene
  作者：De-Jun Zhou、Shu-Qiang Yin、Yun-Chang Fan、Qiang Wang

  DOI：10.1007/s11164-015-2373-y

  日期：2016.6

  6-Diiododiaryl ethers are not only useful blocks to construct substituted diaryl ethers but are also characteristic drug precursors. In this research, a one-pot tandem oxidation of phenols substituted with electron-withdrawing group at the para position by excess diacetoxyiodobenzene is proven as a novel and efficient method for preparing 2,6-diiododiaryl ethers. Using this method, three new 2,6-diiododiaryl

  2,6-二碘二芳基醚不仅是构建取代的二芳基醚的有用嵌段，而且还是特征性的药物前体。在这项研究中，用过量的二乙酰氧基碘代苯对一位置被吸电子基团取代的苯酚进行一锅式串联氧化被证明是制备2，6-二碘二二芳基醚的一种新颖而有效的方法。使用此方法，三个新的2,6-二碘二芳基醚，即3,5-二碘-2-甲氧基-4-苯氧基苯甲酸甲酯（2），3,5-二碘-4-苯氧基苯甲酸甲酯（6）和1-从相应的酚类很容易获得（2,6-二碘-4-硝基苯氧基）苯（7），收率良好。
• Synthesis of carbazoles and dibenzofurans via cross-coupling of o-iodoanilines and o-iodophenols with silylaryl triflates and subsequent Pd-catalyzed cyclization
  作者：Zhijian Liu、Richard C. Larock

  DOI：10.1016/j.tet.2006.10.071

  日期：2007.1

  An efficient route to a variety of carbazoles and dibenzofurans has been developed. It involves the reaction of o-iodoanilines or o-iodophenols with silylaryl triflates in the presence of CsF to afford the N- or O-arylated products, which are subsequently cyclized using a Pd catalyst to carbazoles and dibenzofurans in good to excellent yields. By using this methodology, the carbazole alkaloid, mukonine has been synthesized in 76% overall yield in three steps. (c) 2006 Elsevier Ltd. All rights reserved.
• Structural Studies on Bioactive Compounds. 32. Oxidation of Tyrphostin Protein Tyrosine Kinase Inhibitors with Hypervalent Iodine Reagents
  作者：Geoffrey Wells、Angela Seaton、Malcolm F. G. Stevens

  DOI：10.1021/jm990947f

  日期：2000.4.1

  Hydroxylated styrenes (tyrphostins) undergo oxidation by hypervalent iodine oxidants such as [(diacetoxy)iodo]benzene (DAIB) to give a range of products depending on the structure of the phenolic substrate, the solvent, the oxidant stoichiometry, and the purification strategy. Conditions have been developed to modify the phenolic component of the tyrphostin without affecting the appended substituted-vinyl moiety. Novel products include: unstable 2-acyloxy-2-methoxy-4-(substituted-vinyl)cyclohexadienones and their rearrangement products 2-acyloxy-4-hydroxy-3 -methoxy-1-(substituted-vinyl)benzenes; phenyliodoniophenolates and their rearrangement products iodophenoxytyrphostins; and 3,3'-dialkoxy-2,2'-dihydroxy-5,5'-di(substituted-vinyl)biphenyls. None of these oxidation products displayed enhanced activity in vitro in the NCI 60-cell line panel or in a panel of human breast cancer cell lines, compared to their tyrphostin precursors. The inhibitory activity of three representative tyrphostins (3e,n, 28) was not modulated by aerobic/anaerobic conditions in MCF-7 and MDA 468 cells and was independent of EGFR status in clones of ZR75B cells transfected with this receptor. Basal growth of MCF-7 cells was unaffected by co-administration of the growth factors EGF, TGF-alpha, IGF-I, and IGF-II, and the new agents did not inhibit EGFR and c-erbB2 autaphosphorylation in cell lysates from MDA 468 or SkBr3 cells, respectively, suggesting that receptor tyrosine kinases are not targets for these compounds. Growth stimulation by the tyrphostin 3n in the ER+ breast cell lines MCF-7, T47D, and ZR75-1 was abolished by 1 mu M tamoxifen, suggesting that this compound has estrogen agonist activity.