1-(2-furyl)-1,2,3,4-tetrahydroisoquinoline | 135675-29-5

• 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: 1-(2-furyl)-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 1-(2-furanyl)-1,2,3,4-tetrahydroisoquinoline；1-Furan-2-yl-1,2,3,4-tetrahydro-isoquinoline；1-(furan-2-yl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 135675-29-5
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: NTXMEXFAECISTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  25.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-(2-furyl)-1,2,3,4-tetrahydroisoquinoline 生成 ethyl 1-(2-furyl)-1,2,3,4-tetrahydro-2-isoquinolinecarboxylate
  参考文献：
  名称：

  Quinuclidine derivatives and medicinal composition thereof

  摘要：

  由下列通用式（I）表示的喹诺啉衍生物，其盐、N-氧化物或季铵盐，以及含有这些物质的药物组合物。该化合物对毛细血管M.sub.3受体具有拮抗作用，并可用作预防或治疗泌尿系统疾病、呼吸系统疾病或消化系统疾病的药物。

  公开号：

  US06017927A1
• 作为产物：
  描述：

  1-(furan-2-yl)-3,4-dihydroisoquinoline 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以74%的产率得到1-(2-furyl)-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  A new approach to construction of isoindolo[1,2-a]isoquinoline alkaloids Nuevamine, Jamtine, and Hirsutine via IMDAF reaction

  摘要：

  The interaction between 1-furyl-1,2,3,4-tetrahydroisoquinolines and Unsaturated acids derivatives (acryloyl, methacryloyl, and crotonoyl chloride, maleic and citraconic anhydride) was studied. It was shown that the reaction proceeds via amide formation and Subsequent intramolecular Diels-Alder reaction of the furan (IMDAF). The [4+2] cycloaddition proceeded under mild reaction conditions (25-80 degrees C) and afforded only the exo-adduct in a high yield. With this method, a new approach to the isoindolo[1,2-a]isoquinoline system, the basic structural element of alkaloids Jamtine, Hirsutine, and Nuevamine, is proposed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.024

文献信息

• Selective GABA antagonists, especially isoquinoline derivatives, and their use for treating CNS disorders
  申请人：JOHN WYETH & BROTHER LIMITED

  公开号：EP0419247A2

  公开（公告）日：1991-03-27

  The invention concerns a new method for treating pain and/or CNS disorders using a compound which acts selectively as an antagonist f gamma aminobutyric acid (GABA) at GABA autoreceptors relative to GABAA receptors.

  本发明涉及一种使用一种化合物治疗疼痛和/或中枢神经系统疾病的新方法，该化合物相对于 GABAA 受体，在 GABA 自身受体上选择性地作为拮抗剂 f γ 氨基丁酸（GABA）。
• Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C
  作者：Yue Ji、Mu-Wang Chen、Lei Shi、Yong-Gui Zhou

  DOI：10.1016/s1872-2067(14)60243-6

  日期：2015.1

  A highly selective procedure has been developed for the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines over K3PO4 center dot 3H(2)O-modified Pd/C catalyst. This new method provides facile, atom-economical and environmentally friendly access to 1-substituted-3,4-dihydroisoquinolines without the need for stoichiometric amounts of harmful oxidants. The use of standard Pd/C as a catalyst for this process gave poor chemoselectivity. Pleasingly, the use of a K3PO4 center dot 3H(2)O-modified Pd/C catalyst promoted the partial dehydrogenation of 1-substituted-1,2,3,4-tetrahydroisoquinolines with excellent chemoselectivity by suppressing further dehydroaromatization. Furthermore, conducting the reaction under an atmosphere of oxygen led to further improvements in the chemoselectivity of the dehydrogenation, with the ratio of imine to isoquinoline reaching up to 32/1. The heterogenous Pd/C catalyst could also be recycled and reused at least three times with excellent conversion and chemoselectivity, demonstrating the significantly practical potential of this methodology. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.
• NOVEL QUINUCLIDINE DERIVATIVES AND MEDICINAL COMPOSITION THEREOF
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0801067B1

  公开（公告）日：2003-03-05
• US5118690A
  申请人：——

  公开号：US5118690A

  公开（公告）日：1992-06-02
• US5210088A
  申请人：——

  公开号：US5210088A

  公开（公告）日：1993-05-11