2-iodo-3-methyl-5-methoxybenzoic acid | 1005786-30-0

• 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: 2-iodo-3-methyl-5-methoxybenzoic acid
• 英文别名: 2-iodo-5-methoxy-3-methylbenzoic acid
• CAS: 1005786-30-0
• 化学式: C₉H₉IO₃
• 分子量: 292.073
• InChiKey: PVXUXFKDBHDJQS-UHFFFAOYSA-N

物化性质

• 沸点：
  364.6±42.0 °C(Predicted)
• 密度：
  1.777±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-iodo-3-methyl-5-methoxybenzoic acid 在 氯化亚砜 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.0h， 生成 N-((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)-2-iodo-5-methoxy-3-methylbenzamide
  参考文献：
  名称：

  Catalytic Enantioselective α-Tosyloxylation of Ketones Using Iodoaryloxazoline Catalysts: Insights on the Stereoinduction Process

  摘要：

  A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The alpha-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.

  DOI：

  10.1021/jo302393u
• 作为产物：
  描述：

  (2-iodo-5-methoxy-3-methylphenyl)methanol 在 Jones reagent 、 sodium chlorite 、 sodium dihydrogenphosphate dihydrate 、 双氧水 作用下， 以 丙酮 、 水 、 乙腈 为溶剂， 反应 19.33h， 生成 2-iodo-3-methyl-5-methoxybenzoic acid
  参考文献：
  名称：

  Catalytic Enantioselective α-Tosyloxylation of Ketones Using Iodoaryloxazoline Catalysts: Insights on the Stereoinduction Process

  摘要：

  A family of iodooxazoline catalysts was developed to promote the iodine(III)-mediated alpha-tosyloxylation of ketone derivatives. The alpha-tosyloxy ketones produced are polyvalent chiral synthons. Through this study, we have unearthed a unique mode of stereoinduction from the chiral oxazoline moiety, where the stereogenic center alpha to the oxazoline oxygen atom is significant. Computational chemistry was used to rationalize the stereoinduction process. The catalysts presented promote currently among the best levels of activity and selectivity for this transformation. Evaluation of the scope of the reaction is presented.

  DOI：

  10.1021/jo302393u
• 作为试剂：
  描述：

  对溴苯乙烯 在 Oxone 、 2-iodo-3-methyl-5-methoxybenzoic acid 作用下， 以 水 、 乙腈 为溶剂， 反应 24.0h， 以74%的产率得到4-溴苯甲酸
  参考文献：
  名称：

  Oxidative Cleavage of Olefins by In Situ-Generated Catalytic 3,4,5,6-Tetramethyl-2-iodoxybenzoic Acid/Oxone

  摘要：

  Oxidative cleavage of a variety of olefins to the corresponding ketones/carboxylic acids is shown to occur in a facile manner with 3,4,5,6-tetramethyl-2-iodobenzoic acid (TetMe-IA)/oxone. The simple methodology involves mere stirring of the olefin and catalytic amount (10 mol %) of TetMe-IA and oxone in acetonitrile-water mixture (1:1, v/v) at rt. The reaction mechanism involves initial dihydroxylation of the olefin with oxone, oxidative cleavage by the in situ-generated 3,4,5,6-tetramethyl-2-iodoxybenzoic acid (TetMe-IBX), and oxidation of the aldehyde functionality to the corresponding acid with oxone. Differences in the reactivities of electron-rich and electron-poor double bonds have been exploited to demonstrate chemoselective oxidative cleavage in substrates containing two double bonds.

  DOI：

  10.1021/jo502002w

文献信息

• Modified o-methyl-substituted IBX: room temperature oxidation of alcohols and sulfides in common organic solvents
  作者：Jarugu Narasimha Moorthy、Nidhi Singhal、Kalyan Senapati

  DOI：10.1016/j.tetlet.2007.11.013

  日期：2008.1

  twisting-promoted rate enhancement. Furthermore, the reagent is efficient for selective oxidation of sulfides to sulfoxides, a transformation that otherwise occurs only sluggishly with standard IBX. The facile synthetic accessibility and its mild as well as non-hazardous nature render Me-IBX a stable equivalent of Dess–Martin periodinane reagent in organic oxidations.

  邻位甲基取代的Me-IBX是IBX的第一个修饰类似物，由于两种因素的综合作用，即在低溶解度和高价扭曲促进速率的提高，该化合物在室温下可氧化普通有机溶剂中的醇。此外，该试剂对于将硫化物选择性氧化为亚砜是有效的，否则这种转化只能在标准IBX的情况下缓慢进行。容易获得的合成方法及其温和以及无害的性质使Me-IBX在有机氧化反应中稳定地相当于Dess-Martin高碘烷试剂。
• Enantioselective Synthesis of N–C Axially Chiral Compounds by Cu‐Catalyzed Atroposelective Aryl Amination
  作者：Johanna Frey、Alaleh Malekafzali、Isabel Delso、Sabine Choppin、Françoise Colobert、Joanna Wencel‐Delord

  DOI：10.1002/anie.201914876

  日期：2020.6.2

  N-C axially chiral compounds have emerged recently as appealing motifs for drug design. However, the enantioselective synthesis of such molecules is still poorly developed and surprisingly no metal-catalyzed atroposelective N-arylations have been described. Herein, we disclose an unprecedented Cu-catalyzed atroposelective N-C coupling that proceeds at room temperature. Such mild reaction conditions

  近年来，NC轴向手性化合物已成为药物设计的诱人主题。然而，此类分子的对映选择性合成仍然发展较差，并且令人惊讶地，没有描述金属催化的对映选择性N-芳基化。本文中，我们公开了在室温下进行的前所未有的Cu催化的对位选择性NC偶联。由于使用了高价碘试剂作为高反应性的偶合剂，因此这种温和的反应条件（对于新生成的产品而言，其萎缩能力至关重要）是可操作的。提供了大量的NC轴向手性化合物，具有很高的对映选择性（高达> 99％ee）和良好的收率（高达76％）。