hydroxy(tosyloxy)iodobenzene | 124515-97-5

• 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: hydroxy(tosyloxy)iodobenzene
• 英文别名: Koser's reagent；Hydroxy(phenyl)iodanium;4-methylbenzenesulfonate
• CAS: 124515-97-5
• 化学式: C₆H₆IO*C₇H₇O₃S
• 分子量: 392.214
• InChiKey: LPJGVFLGVZVERG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.25
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  hydroxy(tosyloxy)iodobenzene 以 乙腈 为溶剂， 反应 3.0h， 生成 iodocubyl-1-ammonium tosylate
  参考文献：
  名称：

  Moriarty, R. M.; Khosrowshahi, J. S.; Awasthi, A. K., Synthetic Communications, 1988, vol. 18, # 11, p. 1179 - 1186

  摘要：

  DOI：

文献信息

• Palladium-catalysed cross-coupling reactions of aryl-, alkenyl- and alkynyl-iodonium salts and iodanes with terminal alkynes in aqueous medium
  作者：Suk-Ku Kang、Hong-Woo Lee、Su-Bum Jang、Pil-Su Ho

  DOI：10.1039/cc9960000835

  日期：——

  The ligand-free Pd(OAc)2-catalysed coupling reaction of aryl-, alkenyl- and alkynyl-iodonium tetraflouroborate and iodanes with terminal alkynes proceeds readily in the presence of NaHCO2 in aqueous medium to afford the substituted alkynes in high yields under mild conditions.

  在没有配体的情况下，Pd(OAc)2催化的芳基、烯基和炔基碘鎓四氟硼酸盐与末端炔烃的碘化物在NaHCO2存在下的水相中顺利进行反应，在温和条件下高效地获得了取代炔烃。
• Hypervalent Iodine in Synthesis XXXIII: Palladium-Catalyzed Cross-Coupling Reaction of Potassium Aryltrifluoroborates with Diaryliodonium Salts and Hydroxy(tosyloxy)iodobenzene
  作者：Min Xia、Zhen-Chu Chen

  DOI：10.1080/00397919908086252

  日期：1999.7

  Abstract Potassium aryltrifluoroborates react smoothly with diaryliodonium salts and hydroxy(tosyloxy)iodobenzene, PhI(OH)OTs, under mild conditions in the presence of a palladium catalyst and without added base to afford biaryls in excellent yields.

  摘要 芳基三氟硼酸钾与二芳基碘盐和羟基（甲苯磺酰氧基）碘苯 PhI(OH)OTs 在温和条件下，在钯催化剂存在且不添加碱的情况下顺利反应，以优异的收率得到联芳基化合物。
• (4S)-2,4-Dimethyl-2,4-dihydro-3,6-dioxo-(1H)-pyrazino[2,1-b]quinazolyl tosylate as an electrophilic glycine template
  作者：Sonsoles Martín-Santamaría、Modesta Espada、Carmen Avendaño

  DOI：10.1016/s0040-4020(98)01188-0

  日期：1999.2

  (4S)-2,4-Dimethyl-2,4-dihydro-(1H)-pyrazino[2,1- b]quinazoline-3,6-dione was converted into to the cis- tosylate 2, whose reactivity as an electrophilic glycine template is discussed. It was found that this compound does not give direct S(N)2-type displacement of the tosyloxy group. However, the 1-hydoxy derivative 3, obtained by hydrolysis of 2 with net retention of the stereochemistry, and its 1-methoxy derivative 4a are electrophilic glycine templates. (C) 1999 Elsevier Science Ltd. All rights reserved.

  (4S)-2,4-二甲基-2,4-二氢(1H)-吡嗪并[2,1-b]喹唑啉-3,6-二酮被转化为顺式硫酸酯2，文中讨论了其作为电亲性甘氨酸模板的活性。发现该化合物不会直接发生S(N)2型的硫酸酯基取代反应。然而，其通过水解获得的1-羟基衍生物3（保留了立体化学），及其1-甲氧基衍生物4a则是电亲性甘氨酸模板。 © 1999 Elsevier Science Ltd. 保留所有权利。
• Functionalized cubanes. Oxidative displacement upon methyl 4-iodocubane carboxylate using hypervalent iodine reagents
  作者：Robert M. Moriarty、Jaffar S. Khosrowshahi、Raju Penmasta

  DOI：10.1016/s0040-4039(01)80615-8

  日期：1989.1

  Methyl 4-iodocubane carboxylate undergoes substitution via ligand exchange with the hypervalent reagents C6H5I(OH)OTs, C6H5I(OH)OMs and C6H5ICl2.

  通过与高价试剂C 6 H 5 I（OH）OT，C 6 H 5 I（OH）OM和C 6 H 5 ICl 2进行配体交换，使4-碘古巴甲基甲酸甲酯发生取代。
• Rapid Syntheses of [¹¹C]Arylvinyltrifluoromethanes through Treatment of (<i>E</i>)-Arylvinyl(phenyl)iodonium Tosylates with [¹¹C]Trifluoromethylcopper(I)
  作者：Susovan Jana、Sanjay Telu、Bo Yeun Yang、Mohammad B. Haskali、Jimmy E. Jakobsson、Victor W. Pike

  DOI：10.1021/acs.orglett.0c01705

  日期：2020.6.5

  We report a method for labeling arylvinyltrifluoromethanes with carbon-11 (t(1/2) = 20.4 min) as representatives of a new radiolabeled chemotype that has potential for developing radiotracers for biomedical imaging with positron emission tomography. Treatment of (E)-arylvinyl(phenyl)iodonium tosylates (1a - 1k) with [C-11]CuCF3 gave the corresponding [C-11]arylvinyltrifluoromethanes ([C-11]2a-[C-11]2k) in high radiochemical yields (90-97%) under rapid (2 min) and mild (60 degrees C) conditions.