2-iodo-4-methylphenylacetic acid | 90585-28-7

• 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-4-methylphenylacetic acid
• 英文别名: 2-(2-iodo-4-methylphenyl)acetic acid
• CAS: 90585-28-7
• 化学式: C₉H₉IO₂
• 分子量: 276.074
• InChiKey: WHUIDFGRGBZHMK-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±27.0 °C(Predicted)
• 密度：
  1.778±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 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-iodo-4-methylphenylacetic acid 在 4-二甲氨基吡啶 、 叔丁基锂 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1,4-dimethyl-1,2-dihydrobenzocyclobuten-1-ol
  参考文献：
  名称：

  催化剂和条件控制下钴/铑催化的 C-C 裂解苯并环丁烯醇的多样化酰胺化

  摘要：

  使用二恶唑酮作为酰胺化试剂，实现了钴(III)和铑(III)催化的苯并环丁烯醇的区域和化学选择性酰胺化，通过苯并环丁烯醇的β-碳消除得到三类C-N偶联产物。Co(III)催化的偶联最初提供了可分离的邻- ( N-酰氨基)芳基甲基酮，其可以在条件控制下进一步环化为相应的吲哚衍生物。相比之下，在 Rh(III) 催化剂控制下实现了有效的逐步二酰胺化。化学选择性由催化剂和反应条件共同控制。

  DOI：

  10.1021/acs.orglett.3c01788
• 作为产物：
  描述：

  在 盐酸 、 水 、 高碘酸 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 2-iodo-4-methylphenylacetic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of loxoprofen derivatives

  摘要：

  Non-steroidal anti-inflammatory drugs (NSAIDs) achieve their anti-inflammatory actions through an inhibitory effect on cyclooxygenase (COX). Two COX subtypes, COX-1 and COX-2, are responsible for the majority of COX activity at the gastrointestinal mucosa and in tissues with inflammation, respectively. We previously suggested that both gastric mucosal cell death due to the membrane permeabilization activity of NSAIDs and COX-inhibition at the gastric mucosa are involved in NSAID-induced gastric lesions. We have also reported that loxoprofen has the lowest membrane permeabilization activity among the NSAIDs we tested. In this study, we synthesized a series of loxoprofen derivatives and examined their membrane permeabilization activities and inhibitory effects on COX-1 and COX-2. Among these derivatives, 2-{4'-hydroxy-5-[(2-oxocyclopentyl)methyl]biphenyl-2-yl}propanoate 31 has a specificity for COX-2 over COX-1. Compared to loxoprofen, oral administration of 31 to rats produced fewer gastric lesions but showed an equivalent anti-inflammatory effect. These results suggest that 31 is likely to be a therapeutically beneficial and safer NSAID. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.050

文献信息

• Enantioselective Allylic C−H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis
  作者：Stephen E. Ammann、Wei Liu、M. Christina White

  DOI：10.1002/anie.201603576

  日期：2016.8.8

  The enantioselective synthesis of isochroman motifs has been accomplished by palladium(II)‐catalyzed allylic C−H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide‐oxazoline (ArSOX) ligand. The allylic C−H oxidation reaction proceeds with the broadest scope and highest levels of asymmetric induction reported

  对异氰酸酯基序的对映选择性合成已通过钯（II）催化烯基CH从末端烯烃前体的氧化而完成。实现这一目标的关键是开发和利用新型手性芳基亚砜-恶唑啉（ArSOX）配体。与最宽的范围和不对称诱导最高水平的烯丙基C-H的氧化反应的进行报告的日期（平均92％ee值，13点的例子具有大于90％的ee值）。
• Synthesis of <i>N</i>-Glycosyl-2-oxindoles by Pd-Catalyzed N-Arylation of 1-Amidosugars
  作者：Boris Letribot、Wafa Redjdal、Belkacem Benmerad、Franck Le Bideau、Mouâd Alami、Samir Messaoudi

  DOI：10.1021/acs.orglett.0c01262

  日期：2020.6.5

  An efficient intramolecular Pd-catalyzed N-arylation of o-iodo-amidosugars for the synthesis of N-glycosylated oxindoles has been reported. The coupling reaction takes place in toluene and involves Pd(OAc)2/RuPhos catalytic systems in the presence of K2CO3. This versatile approach was extended successfully to the synthesis of other N-glycosylated heterocycles.

  已经报道了用于合成N-糖基化的羟吲哚的有效的分子内Pd催化的O-碘-氨基糖的N-芳基化。偶联反应在甲苯中进行，并且涉及在K 2 CO 3存在下的Pd（OAc）2 / RuPhos催化体系。这种通用方法已成功扩展到其他N-糖基化杂环的合成。
• Copper-Catalyzed Intramolecular Desymmetric Aryl CO Coupling for the Enantioselective Construction of Chiral Dihydrobenzofurans and Dihydrobenzopyrans
  作者：Wenqiang Yang、Yangyuan Liu、Shasha Zhang、Qian Cai

  DOI：10.1002/anie.201503882

  日期：2015.7.20

  O‐Heterocyclic structures such as 2,3‐dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine. A broad range of substrates are compatible with this CuI‐diamine catalytic system and afford the desired coupling

  诸如2,3-二氢苯并呋喃之类的O杂环结构是许多天然化合物和药物中的关键基序。手性二氢苯并呋喃及其类似物的对映选择性形成是通过铜催化的手性环状1,2-二胺的去对称化策略实现的。各种各样的底物都可以与这种Cu I-二胺催化体系兼容，并在温和条件下以高收率和良好至优异的对映选择性提供具有手性叔或季碳中心的所需偶联产物。
• Mercury in organic chemistry. 26. Synthesis of heterocycles via intramolecular solvomercuration of aryl acetylenes
  作者：Richard C. Larock、L. Wayne Harrison

  DOI：10.1021/ja00327a026

  日期：1984.7
• Expedient Drug Synthesis and Diversification via ortho-C−H Iodination using Recyclable PdI₂ as the Precatalyst
  作者：Tian-Sheng Mei、Dong-Hui Wang、Jin-Quan Yu

  DOI：10.1021/ol1010483

  日期：2010.7.16

  Pd(II)-catalyzed ortho-C H iodination reactions of phenylacetic acid substrates have been achieved using recyclable Pdl(2) as the precatalyst. This class of substrates is incompatible with the classic amide formation/ortho-lithiation/iodination sequence. The power of this new technology is demonstrated by facile drug functionalization and drastically shortened syntheses of the drugs diclofenac and lumiracoxib.