5,5'-diformyl-2,2'-dimethoxydiphenyliodonium bromide | 129866-90-6

• 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: 5,5'-diformyl-2,2'-dimethoxydiphenyliodonium bromide
• 英文别名: 2,2'-dimethoxy-5,5'-diformyl-diphenyl-iodonium bromide；Bis(5-formyl-2-methoxyphenyl)iodanium;bromide
• CAS: 129866-90-6
• 化学式: Br*C₁₆H₁₄IO₄
• 分子量: 477.093
• InChiKey: ODRDOTMNSKXBLP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -3.54
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,5'-diformyl-2,2'-dimethoxydiphenyliodonium bromide 在 sodium hydroxide 、 sodium methylate 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 144.75h， 生成 N¹-4<2-methoxy-5-(3-oxo-3-pentafluorophenoxy-1-propenyl)-phenoxy>-cinnamoyl-N²,N³-di-t-butoxycarbonyl-spermidine
  参考文献：
  名称：

  Nogradi, M.; Lukacs, A.; Szoelloesy, A., ACH - Models in Chemistry, 1994, vol. 131, # 3-4, p. 337 - 344

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲氧基苯甲醛 在 potassium iodate 、 硫酸 、 乙酸酐 、 溶剂黄146 、 potassium bromide 作用下， 生成 5,5'-diformyl-2,2'-dimethoxydiphenyliodonium bromide
  参考文献：
  名称：

  Studies directed toward the synthesis of glycopeptide antibiotic teicoplanin: first synthesis of the N-terminal 14-membered ring

  摘要：

  The N-terminal 14-membered ring formed by an ether linkage between the phenyl moieties of amino acids 1 and 3 of glycopeptide antibiotic teicoplanin 1 plays a crucial role in binding of C-terminal D-Ala-D-Ala residues of the peptidoglycan precursor, thereby inhibiting bacterial cell wall biosynthesis. Herein, the first stereocontrolled synthesis of this very important cyclic peptide 2 is described. The two alpha-arylglycines present in this segment are constructed in optically pure form by diastereoselective Strecker synthesis using alpha-phenylglycinol as chiral auxiliary. Finally, the coupling between the acid function of amino acid 1 and the amino function of amino acid 2 leads to the desired macrocyclization. Optical purity of the synthetic product is determined by NMR studies.

  DOI：

  10.1021/jo00046a031

文献信息

• A general synthetic route towards bastadins. Part 1: Synthesis of the eastern part of bastadins 4–16
  作者：Elias A. Couladouros、Vassilios I. Moutsos

  DOI：10.1016/s0040-4039(99)01429-x

  日期：1999.9

  A general synthetic route for the construction of the eastern part of the macrocyclic bastadins 4–16 is presented. The brominated biaryl ethers are synthesized using the iodonium salt method. The synthesis is accomplished within 18 steps in 15.5% overall yield.

  提出了大环Bastadins 4-16东部的一般合成路线。使用碘鎓盐方法合成溴化的联芳基醚。该合成在18个步骤内完成，总产率为15.5％。
• A general synthetic route towards bastadins. Part 2: Synthesis of the western part of bastadins 4–16, and fully functionalized macrocycle of bastadin 12
  作者：Elias A. Couladouros、Vassilios I. Moutsos

  DOI：10.1016/s0040-4039(99)01430-6

  日期：1999.9

  A general synthetic route for the construction of the western part of the macrocyclic bastadins 4–16 is presented. The western and the eastern segements were coupled using the imidazolide of the corresponding acid. The bromine at position Y2 may be added at this advanced step regiospecifically, strengthening the convergence of the presented approach. Finally, the fully functionalized α,ω-aminoacid

  介绍了大环巴斯塔丁4–16西部构建的一般合成路线。使用相应酸的咪唑内酯偶联西方和东方部分。可以在该高级步骤上区域特异性地添加位置Y 2处的溴，从而增强了所提出方法的收敛性。最后，用EDC使完全官能化的α，ω-氨基酸环化，以72％的收率（总收率3.5％）得到basastin-12的大环。
• Synthesis of diaryl ethers from tyrosine derivatives
  作者：Michael J Crimmin、Allan G Brown

  DOI：10.1016/s0040-4039(00)88904-2

  日期：1990.1

  Diaryl ethers of tyrosine, maintaining optical activity, have been formed through the reaction of a tyrosine derivative with an aryl iodonium salt.

  通过酪氨酸衍生物与芳基碘鎓盐的反应，形成了保持光学活性的酪氨酸二芳基醚。