methyl 5-iodo-2-(methoxymethoxy)benzoate | 51985-46-7

• 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: methyl 5-iodo-2-(methoxymethoxy)benzoate
• 英文别名: Methyl 5-iodo-2-(methoxymethoxy)benzoate
• CAS: 51985-46-7
• 化学式: C₁₀H₁₁IO₄
• 分子量: 322.099
• InChiKey: UIQZURQXEFRAMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯乙烯 、 methyl 5-iodo-2-(methoxymethoxy)benzoate 、 9-methyl-9H-fluorene-9-carbonyl chloride 在 三叔丁基膦 、 N,N-二异丙基乙胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 N-甲基二环己基胺 、 正丁基二(1-金刚烷基)膦 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以34%的产率得到methyl 5-cinnamoyl-2-(methoxymethoxy)benzoate
  参考文献：
  名称：

  Carbonylative Heck Reactions Using CO Generated ex Situ in a Two-Chamber System

  摘要：

  A carbonylative Heck reaction of aryl iodides and styrene derivatives employing a two-chamber system using a stable, crystalline, and nontransition metal based carbon monoxide source is reported. By applying near-stoichiometric amounts of the carbon monoxide precursor, an effective exploitation of the hazardous CO gas is obtained affording chalcone derivatives in good yields. Application to isotope labeling, incorporating (13)CO, was further established.

  DOI：

  10.1021/ol200686h

文献信息

• Silacarboxylic Acids as Efficient Carbon Monoxide Releasing Molecules: Synthesis and Application in Palladium-Catalyzed Carbonylation Reactions
  作者：Stig D. Friis、Rolf H. Taaning、Anders T. Lindhardt、Troels Skrydstrup

  DOI：10.1021/ja208652n

  日期：2011.11.16

  Silacarboxylic acids have been demonstrated to be easy to handle, air-stable carbon monoxide precursors. Different silacarboxylic acids were synthesized from the corresponding chlorosilanes and carbon dioxide, and their decarbonylation, upon treatment with an array of activators, was evaluated. The release of CO from crystalline MePh(2)SiCO(2)H proved to be highly efficient, and it was successfully

  硅羧酸已被证明是易于处理、空气稳定的一氧化碳前体。从相应的氯硅烷和二氧化碳合成了不同的硅羧酸，并评估了它们在用一系列活化剂处理后的脱羰。从结晶 MePh(2)SiCO(2)H 中释放 CO 被证明是高效的，并且它成功地应用于使用接近化学计量数量的一氧化碳前体的钯催化羰基化偶联的选择。最后，证明了 MePh(2)Si(13)CO(2)H 的合成及其在两种生物活性化合物的羰基标记中的应用。
• An Air-Tolerant Approach to the Carbonylative Suzuki–Miyaura Coupling: Applications in Isotope Labeling
  作者：Andreas Ahlburg、Anders T. Lindhardt、Rolf. H. Taaning、Amalie E. Modvig、Troels Skrydstrup

  DOI：10.1021/jo401696c

  日期：2013.10.18

  Carbonylative Suzuki-Miyaura coupling conditions have been developed that proceed without the exclusion of oxygen and in the presence of nondegassed and nondried solvents. By adapting the method to a two-chamber setup, the direct handling of carbon monoxide, produced from stable CO precursors, is avoided. The protocol afforded the desired benzophenones with excellent functional group tolerance and in good yields. Substituting the CO precursor, in the CO-producing chamber, with its carbon-13 labeled version generated the corresponding carbon-13 labeled benzophenones. Finally, the developed system was applied in the synthesis and isotope labeling of two pharmaceuticals, nordazepam and Tricor.