tert-butyl (phenyl(2,4,6-trimethoxyphenyl)methyl)carbamate | 1373935-52-4

• 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: tert-butyl (phenyl(2,4,6-trimethoxyphenyl)methyl)carbamate
• 英文别名: tert-butyl N-[phenyl-(2,4,6-trimethoxyphenyl)methyl]carbamate
• CAS: 1373935-52-4
• 化学式: C₂₁H₂₇NO₅
• 分子量: 373.449
• InChiKey: BIRNGSLUCSBAFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-甲基噻吩 、 tert-butyl (phenyl(2,4,6-trimethoxyphenyl)methyl)carbamate 在 iron(III) chloride hexahydrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 以70%的产率得到2-methyl-5-(phenyl(2,4,5-trimethoxyphenyl)methyl)thiophene
  参考文献：
  名称：

  通过FeCl 3 ·6H 2 O催化的两步法Friedel-Crafts型反应 轻松合成不对称杂芳基取代的三芳基甲烷†

  摘要：

  报道了FeCl 3 ·6H 2 O催化的三组分氮杂-Friedel-Crafts反应的芳族/杂芳族化合物，芳族醛和氨基甲酸叔丁酯。在室温下，在“开瓶”条件下，随后进行了杂芳族化合物与叔丁基二芳基氨基甲酸叔丁酯的Friedel-Crafts型烷基化反应。两步反应对于在室温下在大气气氛下以高收率合成官能化的不对称杂芳基取代的三芳基甲烷特别有用。

  DOI：

  10.1039/c6ob01638c
• 作为产物：
  描述：

  1,3,5-三甲氧基苯 、 benzaldehyde N-boc imine 在 [Ru(TBPP)](SbF₆)₂ 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到tert-butyl (phenyl(2,4,6-trimethoxyphenyl)methyl)carbamate
  参考文献：
  名称：

  RUTHENIUM PORPHYRIN CATALYZED FRIEDEL–CRAFTS TYPE REACTION OF ARENES WITH IMINES

  摘要：

  Cationic ruthenium porphyrin complex was found to be an efficient catalyst for the Friedel-Crafts type reaction of arenes with imines. The use of a structurally rigid tetradentate porphyrin as the equatorial ligand and weakly coordinating axial ligand is the key to bring out the catalytic reactivity of ruthenium for the reaction.

  DOI：

  10.3987/com-12-12556

文献信息

• Bi(OTf)₃-Catalyzed One-Step Catalytic Synthesis of <i>N</i>-Boc or <i>N</i>-Cbz Protected α-Branched Amines
  作者：Jaray Jaratjaroonphong、Surisa Tuengpanya、Sureeporn Ruengsangtongkul

  DOI：10.1021/jo502540k

  日期：2015.1.2

  In this paper, N-Boc and N-Cbz protected alpha-branched amines are synthesized directly from commercially available aromatic/heteroaromatic compounds, aldehydes, and tert-butyl or benzyl carbamate bearing a variety of substituents. Bismuth(III) triflate is found to be a highly effective catalyst for this one-pot, three-component coupling reaction. In addition, the use of mild reaction conditions, low catalytic loading, easy removal of the N-protective group, and one-step synthesis under open-flask are advantages of the present procedure.
• Iodine-catalyzed, one-pot, three-component aza-Friedel–Crafts reaction of electron-rich arenes with aldehyde/carbamate combinations
  作者：Jaray Jaratjaroonphong、Suppachai Krajangsri、Vichai Reutrakul

  DOI：10.1016/j.tetlet.2012.03.024

  日期：2012.5

  Iodine is shown to be an efficient catalyst for a one-step, three-component aza-Friedel-Crafts reaction of activated arenes or heteroarenes with benzyl or tert-butyl carbamates in combination with a wide variety of aldehydes in toluene under 'open-flask' and mild conditions. In the presence of 5 mol % of iodine in toluene at room temperature, the reaction gives the corresponding N-CBz or N-Boc protected a-branched amines, selectively, in good to excellent yields. (C) 2012 Published by Elsevier Ltd.
• NIS-Assisted Aza-Friedel-Crafts Reaction with α-Carbamoysulfides as Precursors of<i>N</i>-Carbamoylimines
  作者：Nicolas George、Mathieu Bekkaye、Aurélien Alix、Jieping Zhu、Géraldine Masson

  DOI：10.1002/chem.201400117

  日期：2014.3.24

  AbstractA general and practical N‐iodosuccinimide (NIS)‐promoted aza‐Friedel–Crafts reaction of various aromatic nucleophiles with N‐acylimines generated in situ from α‐amidosulfides to give a rapid access to highly functionalized amines is described. The newly developed methodology is very mild, fast, efficient, and complementary.
• Facile synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes via the FeCl₃·6H₂O-catalyzed two-step Friedel–Crafts-type reaction
  作者：S. Ruengsangtongkul、P. Taprasert、U. Sirion、J. Jaratjaroonphong

  DOI：10.1039/c6ob01638c

  日期：——

  diarylmethyl carbamate with heteroaromatic compounds under “open-flask” at room temperature was also performed. The two-step reaction was especially useful for the synthesis of functionalized nonsymmetrical heteroaryl-substituted triarylmethanes in good yields under an air atmosphere at room temperature.

  报道了FeCl 3 ·6H 2 O催化的三组分氮杂-Friedel-Crafts反应的芳族/杂芳族化合物，芳族醛和氨基甲酸叔丁酯。在室温下，在“开瓶”条件下，随后进行了杂芳族化合物与叔丁基二芳基氨基甲酸叔丁酯的Friedel-Crafts型烷基化反应。两步反应对于在室温下在大气气氛下以高收率合成官能化的不对称杂芳基取代的三芳基甲烷特别有用。
• RUTHENIUM PORPHYRIN CATALYZED FRIEDEL–CRAFTS TYPE REACTION OF ARENES WITH IMINES
  作者：Takuya Kurahashi、Seijiro Matsubara、Takuma Terada

  DOI：10.3987/com-12-12556

  日期：——

  Cationic ruthenium porphyrin complex was found to be an efficient catalyst for the Friedel-Crafts type reaction of arenes with imines. The use of a structurally rigid tetradentate porphyrin as the equatorial ligand and weakly coordinating axial ligand is the key to bring out the catalytic reactivity of ruthenium for the reaction.