N-(methoxycarbonyl)-1-isopropyl-6,7-dimethyloxy-1,2,3,4-tetrahydroisoquinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: N-(methoxycarbonyl)-1-isopropyl-6,7-dimethyloxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: N-(methoxycarbonyl)-1-isopropyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline；methyl 6,7-dimethoxy-1-propan-2-yl-3,4-dihydro-1H-isoquinoline-2-carboxylate
• 化学式: C₁₆H₂₃NO₄
• 分子量: 293.363
• InChiKey: GVFLGCGSIIQAEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl N-[2-(3,4-dimethoxyphenyl)ethyl]carbamate 、 异丁醛 在 supercritical CO₂ 、 硫酸 作用下， 80.0 ℃ 、16.0 MPa 条件下， 反应 24.0h， 以1.975 g的产率得到N-(methoxycarbonyl)-1-isopropyl-6,7-dimethyloxy-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  Pictet–Spengler reactions in multiphasic supercritical carbon dioxide/CO2-expanded liquid media. In situ generation of carbamates as a strategy for reactions of amines in supercritical carbon dioxide

  摘要：

  酰基-皮克特-斯彭格勒环化反应可通过β-芳基乙胺的氨基甲酸酯衍生物的原位形成，在超临界二氧化碳/二氧化碳膨胀液体介质中实现。

  DOI：

  10.1039/b508151c

文献信息

• Pictet–Spengler reactions in multiphasic supercritical carbon dioxide/CO2-expanded liquid media. In situ generation of carbamates as a strategy for reactions of amines in supercritical carbon dioxide
  作者：Joshua R. Dunetz、Rocco P. Ciccolini、Morgan Fröling、Scott M. Paap、Andrew J. Allen、Andrew B. Holmes、Jefferson W. Tester、Rick L. Danheiser

  DOI：10.1039/b508151c

  日期：——

  Acyl-Pictet–Spengler cyclizations can be achieved in scCO2/CO2-expanded liquid media via the in situ formation of carbamate derivatives of β-arylethylamines.

  酰基-皮克特-斯彭格勒环化反应可通过β-芳基乙胺的氨基甲酸酯衍生物的原位形成，在超临界二氧化碳/二氧化碳膨胀液体介质中实现。
• Synthesis of tetrahydroisoquinolines and isochromans via Pictet–Spengler reactions catalyzed by Brønsted acid–surfactant-combined catalyst in aqueous media
  作者：Akio Saito、Masaki Takayama、Aru Yamazaki、Junko Numaguchi、Yuji Hanzawa

  DOI：10.1016/j.tet.2007.02.123

  日期：2007.5

  Perfluorooctanesulfonic acid (PFOSA), Bronsted acid-surfactant-combined catalyst, efficiently catalyzes the Pictet-Spengler reactions of beta-arylethyl carbamate derivatives with aldehydes in water. The present reaction is accelerated by the addition of 1, 1, 1,3,3,3-hexafluoro-2-propanol (HFIP). PFOSA in HFIP-water (10 v/v%) is also successfully applied to the oxa-Pictet-Spengler reactions of beta-arylethyl alcohol compounds. (C) 2007 Elsevier Ltd. All rights reserved.
• Sustainable chemical processes
  申请人：Dunetz R. Joshua

  公开号：US20070032385A1

  公开（公告）日：2007-02-08

  A method includes preparing a protected amine compound represented by the following structural formula: wherein the dotted line - - - is a covalent bond or no bond. The method includes the step of, in the presence of superatmospheric CO 2 : a) intermolecularly reacting an iminium compound with a nucleophile Nu represented by the following structural diagram: or b) intramolecularly reacting an iminium group of an iminium compound represented by the following structural formula, the iminium compound having a nucleophile: with the nucleophile of the iminium compound, thereby forming the protected amine compound.
• Pictet–Spengler reactions catalyzed by Brønsted acid-surfactant-combined catalyst in water or aqueous media
  作者：Akio Saito、Junko Numaguchi、Yuji Hanzawa

  DOI：10.1016/j.tetlet.2006.11.147

  日期：2007.1

  Perfluorooctanesulfonic acid (PFOSA), Bronsted acid-surfactant-combined catalyst, efficiently catalyzes the Pictet-Spengler reactions of beta-arylethyl carbamate derivatives with aldehydes in water. The present reaction is accelerated by the addition of 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). (c) 2006 Elsevier Ltd. All rights reserved.