2-benzyl-3,4-diethyl-1-methyl-5,6,7,8-tetrahydro-3H-isoquinoline | 1016970-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 2-benzyl-3,4-diethyl-1-methyl-5,6,7,8-tetrahydro-3H-isoquinoline
• CAS: 1016970-67-4
• 化学式: C₂₁H₂₉N
• 分子量: 295.468
• InChiKey: AKMCIPYIAXAPOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-benzyl-3,4-diethyl-1-methyl-5,6,7,8-tetrahydro-3H-isoquinoline 在 palladium on activated charcoal air 、 氢气 作用下， 以 2,2,2-三氟乙醇 、 甲苯 为溶剂， 反应 32.0h， 以39 mg的产率得到2,3-diethyl-1-methyl-5,6,7,8-tetrahydroisoquinoline
  参考文献：
  名称：

  Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation

  摘要：

  A convenient one-pot C-H alkenylation/electrocyclization/aromatization sequence has been developed for the synthesis of highly substituted pyridine derivatives from alkynes and alpha,beta-unsaturated N-benzyl aldimines and ketimines that proceeds through dihydropyridine intermediates. A new class of ligands for C-H activation was developed, providing broader scope for the alkenylation step than could be achieved with previously reported ligands. Substantial information was obtained about the mechanism of the reaction. This included the isolation of a C-H activated complex and its structure determination by X-ray analysis; in addition, kinetic simulations using the Copasi software were employed to determine rate constants for this transformation, implicating facile C-H oxidative addition and slow reductive elimination steps.

  DOI：

  10.1021/ja7104784
• 作为产物：
  描述：

  (E)-N-[1-(cyclohex-1-en-1-yl)ethylidene]-1-phenylmethanamine 、 3-己炔 在 [RhCl(coe)2]2 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以99%的产率得到2-benzyl-3,4-diethyl-1-methyl-5,6,7,8-tetrahydro-3H-isoquinoline
  参考文献：
  名称：

  Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation

  摘要：

  A convenient one-pot C-H alkenylation/electrocyclization/aromatization sequence has been developed for the synthesis of highly substituted pyridine derivatives from alkynes and alpha,beta-unsaturated N-benzyl aldimines and ketimines that proceeds through dihydropyridine intermediates. A new class of ligands for C-H activation was developed, providing broader scope for the alkenylation step than could be achieved with previously reported ligands. Substantial information was obtained about the mechanism of the reaction. This included the isolation of a C-H activated complex and its structure determination by X-ray analysis; in addition, kinetic simulations using the Copasi software were employed to determine rate constants for this transformation, implicating facile C-H oxidative addition and slow reductive elimination steps.

  DOI：

  10.1021/ja7104784

文献信息

• Highly Diastereoselective Synthesis of Tetrahydropyridines by a C–H Activation–Cyclization–Reduction Cascade
  作者：Simon Duttwyler、Colin Lu、Arnold L. Rheingold、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ja2119833

  日期：2012.3.7

  A versatile reaction cascade leading to highly substituted 1,2,3,6-tetrahydropyridines has been developed. It comprises rhodium(I)-catalyzed C-H activation-alkyne coupling followed by electrocyclization and subsequent acid/borohydride-promoted reduction. This one-pot procedure affords the target compounds in up to 95% yield with >95% diastereomeric purity.

  已开发出一种可产生高度取代的 1,2,3,6-四氢吡啶的通用反应级联。它包括铑 (I) 催化的 CH 活化-炔烃偶联，然后是电环化和随后的酸/硼氢化物促进的还原。这一一锅法可提供高达 95% 的收率和 >95% 非对映体纯度的目标化合物。