2-(2-methoxyphenyl)-1,2,3,4-tetrahydroquinoline | 1242160-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(2-methoxyphenyl)-1,2,3,4-tetrahydroquinoline
• CAS: 1242160-43-5
• 化学式: C₁₆H₁₇NO
• mdl: MFCD21400099
• 分子量: 239.317
• InChiKey: UBBAIBBWIOZBQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-methoxyphenyl)-1,2,3,4-tetrahydroquinoline 在 1-phenyl-N-(3,4,5-trimethoxyphenyl)ethan-1-imine 、 C₅₀H₅₉O₄P 作用下， 以 甲苯 为溶剂， 反应 72.0h， 以77%的产率得到
  参考文献：
  名称：

  Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines

  摘要：

  四氢喹啉与酮亚胺在手性磷酸存在下的标题反应以高效转化和优异对映选择性进行。

  DOI：

  10.1039/c5cc06436h
• 作为产物：
  描述：

  2-(2-甲氧基苯基)喹啉 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 生成 2-(2-methoxyphenyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines

  摘要：

  四氢喹啉与酮亚胺在手性磷酸存在下的标题反应以高效转化和优异对映选择性进行。

  DOI：

  10.1039/c5cc06436h

文献信息

• Hydrogenation of ortho-nitrochalcones over Pd/C as a simple access to 2-substituted 1,2,3,4-tetrahydroquinolines
  作者：Angela Patti、Sonia Pedotti

  DOI：10.1016/j.tet.2010.05.090

  日期：2010.7

  The preparation of some 2-substituted-1,2,3,4-tetrahydroquinoline has been achieved by the one-pot reductive intramolecular cyclization of ortho-nitrochalcones with gaseous hydrogen in the presence of a Pd/C catalyst and the best selectivity was observed using CH2Cl2 as solvent. The method is operationally simple and versatile since ortho-nitrocalchones are easily accessible by Claisen-Schmidt condensation of 2-nitrobenzaldehydes and enolizable ketones. Selected examples on structurally different substrates have been considered and a novel tetrahydroquinoline and a benzo[h]tetrahydroquinoline were prepared and characterised. (C) 2010 Elsevier Ltd. All rights reserved.
• Chiral phosphoric acid catalyzed oxidative kinetic resolution of cyclic secondary amine derivatives including tetrahydroquinolines by hydrogen transfer to imines
  作者：Kodai Saito、Hiromitsu Miyashita、Takahiko Akiyama

  DOI：10.1039/c5cc06436h

  日期：——

  The title reaction of tetrahydroquinolines with ketimine in the presence of chiral phosphoric acid proceeded with efficient conversion and excellent enantioselectivities.

  四氢喹啉与酮亚胺在手性磷酸存在下的标题反应以高效转化和优异对映选择性进行。
• Fluorobissulfonylmethyl Iodides: An Efficient Scaffold for Halogen Bonding Catalysts with an sp³-Hybridized Carbon–Iodine Moiety
  作者：Kohei Matsuzaki、Hiroto Uno、Etsuko Tokunaga、Norio Shibata

  DOI：10.1021/acscatal.8b01330

  日期：2018.7.6

  The halogen-bond donors FBSM-I and FBDT-I, which contain an sp(3)-hybridized carbon iodine (C-sp(3)-I) moiety, were designed and synthesized. The highly electron-withdrawing nature of the fluorobissulfonyl-methane scaffold leads to the generation of sigma-holes on the surface of the iodine atoms in FBSM-I and FBDT-I. Mukaiyama aldol reactions and hydrogen-transfer reductions are efficiently catalyzed by FBSM-I and FBDT-I under neutral and mild reaction conditions. The driving force for these transformations should be the halogen bonding induced by FBSM-I and FBDT-I, which was confirmed by DFT calculations, single crystal X-ray diffraction analyses, and NMR titrations.