benzyl N-[phenyl(2,4,6-trimethoxyphenyl)methyl]carbamate | 1373935-45-5

• 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: benzyl N-[phenyl(2,4,6-trimethoxyphenyl)methyl]carbamate
• 英文别名: benzyl (phenyl)(2,4,6-trimethoxyphenyl)methylcarbamate；benzyl N-[phenyl-(2,4,6-trimethoxyphenyl)methyl]carbamate
• CAS: 1373935-45-5
• 化学式: C₂₄H₂₅NO₅
• 分子量: 407.466
• InChiKey: PQPOZRSPNAMJFI-UHFFFAOYSA-N

物化性质

• 沸点：
  595.0±50.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1,3,5-三甲氧基苯 、 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以95%的产率得到benzyl N-[phenyl(2,4,6-trimethoxyphenyl)methyl]carbamate
  参考文献：
  名称：

  NIS-Assisted Aza-Friedel-Crafts Reaction with α-Carbamoysulfides as Precursors ofN-Carbamoylimines

  摘要：

  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.

  DOI：

  10.1002/chem.201400117

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.
• 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.
• 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.