2-碘-3,5-二甲基苯甲酸 | 198220-36-9

• 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: 2-碘-3,5-二甲基苯甲酸
• 英文名称: 3,5-dimethyl-2-iodobenzoic acid
• 英文别名: 2-Iodo-3,5-dimethylbenzoic acid
• CAS: 198220-36-9
• 化学式: C₉H₉IO₂
• 分子量: 276.074
• InChiKey: BIZQUVFMTMOTGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-碘-3,5-二甲基苯甲酸 在 Oxone 作用下， 以 水 为溶剂， 反应 5.0h， 以82%的产率得到3,5-dimethyl-2-iodoxybenzoic acid
  参考文献：
  名称：

  Twist Does a Twist to the Reactivity: Stoichiometric and Catalytic Oxidations with Twisted Tetramethyl-IBX

  摘要：

  The methyl groups in TetMe-IBX lower the activation energy corresponding to the rate-determining hypervalent twisting (theoretical calculations), and the steric relay between successive methyl groups twists the structure, which manifests in significant solubility in common organic solvents. Consequently, oxidations of alcohols and sulfides occur at room temperature in common organic solvents. In situ generation of the reactive TetMe-IBX from its precursor iodo-acid, i.e., 3,4,5,6-tetramethyl-2-iodobenzoic acid, in the presence of oxone as a co-oxidant facilitates the oxidation of diverse alcohols at room temperature.

  DOI：

  10.1021/jo201491q
• 作为产物：
  描述：

  3,5-二甲基苯甲酸 在 盐酸 、 tin 、 硫酸 、 硝酸 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 19.7h， 生成 2-碘-3,5-二甲基苯甲酸
  参考文献：
  名称：

  Twist Does a Twist to the Reactivity: Stoichiometric and Catalytic Oxidations with Twisted Tetramethyl-IBX

  摘要：

  The methyl groups in TetMe-IBX lower the activation energy corresponding to the rate-determining hypervalent twisting (theoretical calculations), and the steric relay between successive methyl groups twists the structure, which manifests in significant solubility in common organic solvents. Consequently, oxidations of alcohols and sulfides occur at room temperature in common organic solvents. In situ generation of the reactive TetMe-IBX from its precursor iodo-acid, i.e., 3,4,5,6-tetramethyl-2-iodobenzoic acid, in the presence of oxone as a co-oxidant facilitates the oxidation of diverse alcohols at room temperature.

  DOI：

  10.1021/jo201491q

文献信息

• Total Synthesis of (−)-Bacchopetiolone via an Asymmetric Hydroxylative Phenol Dearomatization/[4+2]-Dimerization Cascade Promoted by a Novel Salen-Type Chiral Iodane
  作者：Romain Coffinier、Mourad El Assal、Philippe A. Peixoto、Cyril Bosset、Karinne Miqueu、Jean-Marc Sotiropoulos、Laurent Pouységu、Stéphane Quideau

  DOI：10.1021/acs.orglett.6b00224

  日期：2016.3.4

  The first total and biomimetic synthesis of the natural bis(sesquiterpene) (−)-bacchopetiolone (revised structure) was completed through a highly diastereoselective hydroxylative phenol dearomatization/[4+2]-dimerization cascade conversion of (+)-curcuphenol using a novel C2-symmetrical chiral Salen-type bis(λ5-iodane).

  天然双（倍半萜烯）（-）-bacchopetiolone（修改后的结构）的第一个总合成和仿生合成通过使用一种新型的（+）-curcuphenol的高度非对映选择性羟基化苯酚脱芳香化/ [4 + 2]-二聚级联转化完成c ^ 2 -symmetrical手性Salen型双（λ 5 -iodane）。
• 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％）。
• Benzoic acid derivatives
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：EP0181526A1

  公开（公告）日：1986-05-21

  Benzoic acid derivatives of the formula: wherein n is an integer of 0 to 2: R1 to R3 which may be the same or different each represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or nitro group; R4 is a hydroxyl group or the group -NHZ (Z is hydrogen atom or a lower alkyl group), or an alkali metal salts thereof are useful as an infection control agent. These derivatives excepting compounds of the formula above wherein n is 0 or 1; any one of R, to R3 is 5-chloro, 5-methoxy or 5-nitro and the remainder is a hydrogen atom; and R4 is a hydroxyl group; and compounds of the formula wherein n is 0 or 1; two of R, to R3 are 3,5-dichloro or 3,5-dinitro and the remainder is a hydrogen atom; and R4 is a hydroxy group) are novel, and they were first prepared in this invention.

  式中的苯甲酸衍生物： 其中 n 为 0 至 2 的整数：R1 至 R3 可以相同或不同，各自代表氢原子、卤素原子、低级烷基、低级烷氧基或硝基；R4 为羟基或基团 -NHZ（Z 为氢原子或低级烷基），或其碱金属盐，可用作感染控制剂。 这些衍生物除了上式化合物（其中n为0或1；R，至R3中的任何一个为5-氯、5-甲氧基或5-硝基，其余为氢原子；R4为羟基；以及式中化合物（其中n为0或1；R，至R3中的两个为3，5-二氯或3，5-二硝基，其余为氢原子；R4为羟基）是新颖的，它们在本发明中首次制备。
• Ligand-Enabled Palladium-Catalyzed [3 + 2] Annulation of Aryl Iodides with Maleimides via C(sp3)–H Activation
  作者：Feng Wei、Yanghui Zhang

  DOI：10.1021/acs.orglett.4c02138

  日期：2024.7.26

  Palladium-catalyzed intermolecular [3 + 2] annulation reactions via C–H activation represent a powerful and charming tool for assembling cyclopentanes. Herein, we have developed a strategy for the palladium-catalyzed intermolecular alkene-relayed annulation reaction of aryl iodides and maleimides via C(sp3)–H activation for the construction of polycyclic structures. In contrast to directed-group-enabled

  钯催化的通过 C-H 活化的分子间 [3 + 2] 成环反应是组装环戊烷的强大而迷人的工具。在此，我们开发了一种钯催化芳基碘化物和马来酰亚胺分子间烯烃中继环化反应的策略，通过 C(sp 3 )–H 活化来构建多环结构。与定向基团分子间马来酰亚胺中继的 [3 + 2] 成环反应相比，该方案因其利用芳基碘化物作为底物而脱颖而出。值得注意的是，单保护氨基酸作为配体在该反应中发挥了至关重要的作用，这在有机卤化物引发的 C-H 活化反应中很少观察到。
• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18