methyl 2-(((3,4-dimethoxyphenethyl)carbamoyl)oxy)benzoate

• 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 2-(((3,4-dimethoxyphenethyl)carbamoyl)oxy)benzoate
• 英文别名: Methyl 2-[2-(3,4-dimethoxyphenyl)ethylcarbamoyloxy]benzoate；methyl 2-[2-(3,4-dimethoxyphenyl)ethylcarbamoyloxy]benzoate
• 化学式: C₁₉H₂₁NO₆
• 分子量: 359.379
• InChiKey: KZMGXHYXYFTBIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(((3,4-dimethoxyphenethyl)carbamoyl)oxy)benzoate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到6,7-二甲氧基-3,4-二氢-异喹啉-1-酮
  参考文献：
  名称：

  Facile Synthesis of 5- to 7-Membered Benzolactam Compounds via Strongly Facilitated Electrophilic Aromtic Substitution Reaction†

  摘要：

  We employed our system to activate aromatic ring-tethered carbamate compounds with trifluoromethanesulfonic acid to obtain benzolactams with 5- to 7-membered rings, and examined the substrate scope and limitations of this activation method. In 5-membered ring formation, a halogen group on the aromatic ring did not greatly affect the reaction yield, but other electron-donating groups inhibited the cyclization reaction, and various side-reactions occurred. In 7-membered ring formation, eletron-donating groups on aromatic ring promoted the cyclization reaction, but cyclization of electron-deficient aromatic rings did not proceed well. The 6-membered ring formation reaction showed the greatest substrate generality.

  DOI：

  10.3987/com-15-s(t)60
• 作为产物：
  描述：

  dimethyl 2,2'-(carbonylbis(oxy))dibenzoate 在 三氟甲磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 15.08h， 生成 methyl 2-(((3,4-dimethoxyphenethyl)carbamoyl)oxy)benzoate
  参考文献：
  名称：

  氨基甲酸酯活化率的提高使得能够合成四环苯并内酰胺：8-氧代berbines及其5和7元C环同系物

  摘要：

  开发了直接酰胺化芳族环系N-氨基甲酰基四氢异喹啉底物的途径。该途径使人们能够普遍获得8-氧小ber碱及其5和7元C环同系物。它克服了导致异喹啉主链破坏的不希望的串联副反应，这种副反应在我们先前报道的超酸性氨基甲酸酯活化方法下不可避免地发生。

  DOI：

  10.1039/d0ob02096f

文献信息

• Enhancement of the carbamate activation rate enabled syntheses of tetracyclic benzolactams: 8-oxoberbines and their 5- and 7-membered C-ring homologues
  作者：Hiroaki Kurouchi

  DOI：10.1039/d0ob02096f

  日期：——

  A route to the direct amidation of aromatic-ring-tethered N-carbamoyl tetrahydroisoquinoline substrates was developed. This route enabled general access to 8-oxoberberines and their 5- and 7- membered C-ring homologues. It overcomes the undesired tandem side-reactions that result in the destruction of the isoquinoline backbone, which inevitably occurred under our previously reported superacidic carbamate

  开发了直接酰胺化芳族环系N-氨基甲酰基四氢异喹啉底物的途径。该途径使人们能够普遍获得8-氧小ber碱及其5和7元C环同系物。它克服了导致异喹啉主链破坏的不希望的串联副反应，这种副反应在我们先前报道的超酸性氨基甲酸酯活化方法下不可避免地发生。
• Facile Synthesis of 5- to 7-Membered Benzolactam Compounds via Strongly Facilitated Electrophilic Aromtic Substitution Reaction†
  作者：Tomohiko Ohwada、Hiroaki Kurouchi、Yuko Otani

  DOI：10.3987/com-15-s(t)60

  日期：——

  We employed our system to activate aromatic ring-tethered carbamate compounds with trifluoromethanesulfonic acid to obtain benzolactams with 5- to 7-membered rings, and examined the substrate scope and limitations of this activation method. In 5-membered ring formation, a halogen group on the aromatic ring did not greatly affect the reaction yield, but other electron-donating groups inhibited the cyclization reaction, and various side-reactions occurred. In 7-membered ring formation, eletron-donating groups on aromatic ring promoted the cyclization reaction, but cyclization of electron-deficient aromatic rings did not proceed well. The 6-membered ring formation reaction showed the greatest substrate generality.