1-acetoxy-1,2-benziodoxol-3(1H)-one 1-oxide | 135394-78-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1-acetoxy-1,2-benziodoxol-3(1H)-one 1-oxide
• 英文别名: 1-acetoxy-1,2-benziodoxol-2(1H)-one 1-oxide；1-(Acetyloxy)-1lambda~5~,2-benziodoxole-1,3(1H)-dione；(1,3-dioxo-1λ5,2-benziodoxol-1-yl) acetate
• CAS: 135394-78-4
• 化学式: C₉H₇IO₅
• 分子量: 322.056
• InChiKey: OAZJMZBCZRBVPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  频哪醇 、 1-acetoxy-1,2-benziodoxol-3(1H)-one 1-oxide 生成 1-((3-hydroxy-2,3-dimethylbutan-2-yl)oxy)-1-oxo-15-benzo[d][1,2]iodaoxol-3(1H)-one
  参考文献：
  名称：

  Hypervalent Iodine Oxidants:  Structure and Kinetics of the Reactive Intermediates in the Oxidation of Alcohols and 1,2-Diols by o-Iodoxybenzoic Acid (IBX) and Dess−Martin Periodinane. A Comparative ¹H-NMR Study

  摘要：

  Alcohols and 1,2-diols oxidation by o-iodoxybenzoic acid (IBX) has been examined by H-1-NMR spectroscopy. Reversible formation of reactive intermediates, iodic esters 5, has been observed, and their structures in DMSO-d(6) solution have been defined as 10-I-4 axial alkoxyiodinane oxides by comparison of the chemical shift difference data with those obtained for Dess-Martin periodinane (DMP)-alcoholate and -diolate adducts. The dichotomous behavior exhibited by IBX and DMP with 1,2-diols can be explained in terms of the different architecture of the reactive intermediates involved in the oxidation. With aliphatic alcohols, kinetic evidences support a two-step reaction mechanism involving a fast pre-equilibrium step leading to 5, followed by a rate-determining disproportionation step. With electronically activated benzyl alcohol, the attainment of preequilibrium is largely dependent on initial water concentration as a consequence of a particularly high k(2) value. The influence of the alcohol structure on measured equilibrium (K-eq) and rate constants (k(2)) and the effect of water on the overall reaction rate are discussed.

  DOI：

  10.1021/jo961044m
• 作为产物：
  描述：

  戴斯-马丁氧化剂 在 水 作用下， 以 氘代二甲亚砜 为溶剂， 生成 1-acetoxy-1,2-benziodoxol-3(1H)-one 1-oxide
  参考文献：
  名称：

  Hypervalent Iodine Oxidants:  Structure and Kinetics of the Reactive Intermediates in the Oxidation of Alcohols and 1,2-Diols by o-Iodoxybenzoic Acid (IBX) and Dess−Martin Periodinane. A Comparative ¹H-NMR Study

  摘要：

  Alcohols and 1,2-diols oxidation by o-iodoxybenzoic acid (IBX) has been examined by H-1-NMR spectroscopy. Reversible formation of reactive intermediates, iodic esters 5, has been observed, and their structures in DMSO-d(6) solution have been defined as 10-I-4 axial alkoxyiodinane oxides by comparison of the chemical shift difference data with those obtained for Dess-Martin periodinane (DMP)-alcoholate and -diolate adducts. The dichotomous behavior exhibited by IBX and DMP with 1,2-diols can be explained in terms of the different architecture of the reactive intermediates involved in the oxidation. With aliphatic alcohols, kinetic evidences support a two-step reaction mechanism involving a fast pre-equilibrium step leading to 5, followed by a rate-determining disproportionation step. With electronically activated benzyl alcohol, the attainment of preequilibrium is largely dependent on initial water concentration as a consequence of a particularly high k(2) value. The influence of the alcohol structure on measured equilibrium (K-eq) and rate constants (k(2)) and the effect of water on the overall reaction rate are discussed.

  DOI：

  10.1021/jo961044m

文献信息

• NOVEL HETEROCYCLIC AROMATIC COMPOUND AND POLYMER
  申请人：Kita Yasuyuki

  公开号：US20110190461A1

  公开（公告）日：2011-08-04

  A heterocycle-containing aromatic compound represented by the formula: A-B, and an electrically conductive polymer obtained by oxidative polymerization of the heterocycle-containing aromatic compound as a monomer are provided. In the above formula, A represents a substituted or unsubstituted thiophene ring group, or a substituted or unsubstituted pyrrole ring group; B represents a substituted or unsubstituted hydrocarbon aromatic ring group, a substituted or unsubstituted thiophene ring group, or a substituted or unsubstituted pyrrole ring group; the ring represented by A and the ring represented by B are directly linked; however, A and B represent structures that are different from each other. The compound can be produced by a coupling reaction using a hypervalent iodine reactant.

  提供一种含杂环芳香化合物的分子，其化学式为A-B，以及通过将含杂环芳香化合物氧化聚合得到的电导性高分子作为单体。在上述化学式中，A代表取代或未取代的噻吩环基团或取代或未取代的吡咯环基团；B代表取代或未取代的碳氢芳香环基团、取代或未取代的噻吩环基团或取代或未取代的吡咯环基团。由A和B代表的环直接连接；但是，A和B代表的结构不同。该化合物可以通过使用高价碘试剂进行偶联反应来制备。
• Acceleration of the Dess-Martin Oxidation by Water
  作者：Stephanie D. Meyer、Stuart L. Schreiber

  DOI：10.1021/jo00103a067

  日期：1994.12
• Dess, Daniel B.; Martin, Journal of the American Chemical Society, 1991, vol. 113, # 19, p. 7277 - 7287
  作者：Dess, Daniel B.、Martin

  DOI：——

  日期：——
• Hypervalent Iodine Oxidants:  Structure and Kinetics of the Reactive Intermediates in the Oxidation of Alcohols and 1,2-Diols by <i>o</i>-Iodoxybenzoic Acid (IBX) and Dess−Martin Periodinane. A Comparative ¹H-NMR Study
  作者：Sergio De Munari、Marco Frigerio、Marco Santagostino

  DOI：10.1021/jo961044m

  日期：1996.1.1

  Alcohols and 1,2-diols oxidation by o-iodoxybenzoic acid (IBX) has been examined by H-1-NMR spectroscopy. Reversible formation of reactive intermediates, iodic esters 5, has been observed, and their structures in DMSO-d(6) solution have been defined as 10-I-4 axial alkoxyiodinane oxides by comparison of the chemical shift difference data with those obtained for Dess-Martin periodinane (DMP)-alcoholate and -diolate adducts. The dichotomous behavior exhibited by IBX and DMP with 1,2-diols can be explained in terms of the different architecture of the reactive intermediates involved in the oxidation. With aliphatic alcohols, kinetic evidences support a two-step reaction mechanism involving a fast pre-equilibrium step leading to 5, followed by a rate-determining disproportionation step. With electronically activated benzyl alcohol, the attainment of preequilibrium is largely dependent on initial water concentration as a consequence of a particularly high k(2) value. The influence of the alcohol structure on measured equilibrium (K-eq) and rate constants (k(2)) and the effect of water on the overall reaction rate are discussed.