(3-iodophenyl)methyl acetate | 116943-45-4

• 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: (3-iodophenyl)methyl acetate
• 英文别名: 3-iodobenzyl acetate；acetic acid-(3-iodo-benzyl ester)；3-Jod-α-acetoxy-toluol；Essigsaeure-(3-jod-benzylester)；(3-Jod-benzyl)-acetat
• CAS: 116943-45-4
• 化学式: C₉H₉IO₂
• 分子量: 276.074
• InChiKey: FLWONTPWLQLFNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-乙酰基-L-半胱氨酸甲酯 、 (3-iodophenyl)methyl acetate 在 tris-(dibenzylideneacetone)dipalladium(0) 1,1'-双(二苯基膦)二茂铁 、 三乙胺 作用下， 以 various solvent(s) 为溶剂， 反应 2.0h， 以77%的产率得到(R)-3-(3-Acetoxymethyl-phenylsulfanyl)-2-acetylamino-propionic acid methyl ester
  参考文献：
  名称：

  钯催化的芳族巯基酸衍生物的新合成

  摘要：

  在由Pd 2 dba 3和dppf原位制备的钯催化剂的存在下，N-乙酰基-L-半胱氨酸甲酯（1）在温和的条件下与芳基碘化物2反应，以中等至良好的产率得到S-芳基衍生物3。

  DOI：

  10.1016/0040-4039(95)00677-5
• 作为产物：
  描述：

  3-碘苯甲醇 、 乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (3-iodophenyl)methyl acetate
  参考文献：
  名称：

  Highly selective cross-coupling reactions of aryl(halo)silanes with aryl halides: A general and practical route to functionalized biaryls

  摘要：

  The palladium catalyzed cross-coupling reaction of aryl halides with aryl(halo)silanes (halogen= F, Cl) gives good yields of unsymmetrical biaryls and p-terphenyls. The reaction takes place smoothly in N,N-dimethylformamide in the presence of an appropriate palladium catalyst and potassium fluoride. Since this reaction is tolerant of a variety of reactive functional groups, highly functionalized 4,4'-, 3,4'-, 2,4'- and even sterically crowded 2,2'-disubstituted biaryls can be obtained in moderate to high yields. The synthetic utility of the method has been demonstrated by its application to a short synthesis of liquid crystals. Mechanistic aspects of transmetalation of an aryl(fluoro)silicate intermediate with a palladium complex are discussed on the basis of the substituent effects on the rate of the cross-coupling reactions.

  DOI：

  10.1016/s0040-4020(01)85554-x

文献信息

• Palladium Catalyzed Regioselective C4‐Arylation and Olefination of Indoles and Azaindoles
  作者：Neetipalli Thrimurtulu、Arnab Dey、Anurag Singh、Kuntal Pal、Debabrata Maiti、Chandra M. R. Volla

  DOI：10.1002/adsc.201801378

  日期：2019.3.15

  A convergent strategy for the synthesis of biologically relevant C4‐substituted indole scaffolds was demonstrated using Pd(II)‐catalyzed remote C−H functionalization of indoles and azaindoles. The reaction displays high regioselectivity for the C4‐position of indole‐3‐carbaldehydes using glycine as an inexpensive transient directing group. Notable features of this transformation include the selective

  使用Pd（II）催化的吲哚和氮杂吲哚的远程CH功能化，证明了生物相关的C4取代的吲哚支架合成的收敛策略。该反应使用甘氨酸作为廉价的瞬态导向基团，对吲哚-3-甲醛的C4位具有很高的区域选择性。该转变的显着特征包括六元palladacyle的选择性形成和出色的官能团耐受性。
• Orchestrated Triple CH Activation Reactions Using Two Directing Groups: Rapid Assembly of Complex Pyrazoles
  作者：Weibo Yang、Shengqing Ye、Dewey Fanning、Timothy Coon、Yvonne Schmidt、Paul Krenitsky、Dean Stamos、Jin-Quan Yu

  DOI：10.1002/anie.201410462

  日期：2015.2.16

  sequential triple CH activation reaction directed by a pyrazole and an amide group leads to the well‐controlled construction of sterically congested dihydrobenzo[e]indazole derivatives. This cascade reaction demonstrates that the often problematic competing CH activation pathways in the presence of multiple directing groups can be harvested by design to improve step economy in synthesis. Pyrazole as a

  由吡唑和酰胺基团引导的连续三重C - H活化反应导致空间拥挤的二氢苯并[e]吲唑衍生物的良好控制的结构。这种级联反应表明，在存在多个导向基团的情况下，经常存在问题的竞争性 C → H 活化途径可以通过设计来收获，以提高合成中的步骤经济性。吡唑作为相对较弱的配位基团首次被证明可以直接指导C - H活化。
• Palladium-Catalyzed Reaction of Aryl Iodides with Acetic Anhydride. A Carbon Monoxide-Free Synthesis of Acetophenones
  作者：Sandro Cacchi、Giancarlo Fabrizi、Federica Gavazza、Antonella Goggiamani

  DOI：10.1021/ol027243b

  日期：2003.2.1

  [reaction: see text] The palladium-catalyzed reaction of aryl iodides with acetic anhydride provides a straightforward and experimentally simple carbon monoxide-free route to acetophenones. The reaction tolerates a wide range of functionalized aryl iodides. Acetophenones are isolated in excellent yield with a variety of neutral, slightly electron-rich, and slightly electron-poor aryl iodides, whereas

  [反应：见正文]芳基碘化物与乙酸酐的钯催化反应为苯乙酮提供了一种直接且实验简单的无一氧化碳的途径。该反应可耐受各种官能化的芳基碘化物。苯乙酮以优异的收率与各种中性，略带电子富集和略带电子贫化的芳基碘化物分离，而使用含有强吸电子取代基的芳基碘化物则获得中等收率。
• N-Heterocyclic Carbene Ligand-Enabled C(sp³)−H Arylation of Piperidine and Tetrahydropyran Derivatives
  作者：Shengqing Ye、Weibo Yang、Timothy Coon、Dewey Fanning、Tim Neubert、Dean Stamos、Jin-Quan Yu

  DOI：10.1002/chem.201600191

  日期：2016.3.24

  PdII‐catalyzed C(sp3)−H arylation of saturated heterocycles with a wide range of aryl iodides is enabled by an N‐heterocyclic carbene (NHC) ligand. A C(sp3)−H insertion step by the PdII/NHC complex in the absence of ArI is demonstrated experimentally for the first time. Experimental data suggests that the previously established NHC‐mediated Pd0/PdII catalytic manifold does not operate in this reaction

  N杂环卡宾（NHC）配体可实现Pd II催化的饱和杂环与各种芳基碘的C（sp 3）-H芳基化反应。首次通过实验证明了在不存在ArI的情况下，Pd II / NHC络合物的AC（sp 3）-H插入步骤。实验数据表明，先前建立的NHC介导的Pd 0 / Pd II催化歧管在该反应中不起作用。该转化为使药学上相关的哌啶和四氢吡喃环系统多样化提供了一种新方法。
• Tommila, Annales Academiae Scientiarum Fennicae, Series A, 1942, vol. 59, # 4, p. 3,4
  作者：Tommila

  DOI：——

  日期：——