1-(furan-2-yl)-3,4-dihydroisoquinoline | 177272-65-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 1-(furan-2-yl)-3,4-dihydroisoquinoline
• 英文别名: 1-(2-furyl)-3,4-dihydroisoquinoline；1-furyl-3,4-dihydroisoquinoline
• CAS: 177272-65-0
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: FPFBTNSNJKDVAR-UHFFFAOYSA-N

物化性质

• 沸点：
  302.1±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  1-(2-furyl)-1,2,3,4-tetrahydroisoquinoline 在 potassium phosphate monohydrate 、 5%-palladium/activated carbon 、 氧气 作用下， 以 乙腈 为溶剂， 以88%的产率得到1-(furan-2-yl)-3,4-dihydroisoquinoline
  参考文献：
  名称：

  Highly selective partial dehydrogenation of tetrahydroisoquinolines using modified Pd/C

  摘要：

  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.

  DOI：

  10.1016/s1872-2067(14)60243-6

文献信息

• A Highly Efficient and Enantioselective Access to Tetrahydroisoquinoline Alkaloids: Asymmetric Hydrogenation with an Iridium Catalyst
  作者：Mingxin Chang、Wei Li、Xumu Zhang

  DOI：10.1002/anie.201104476

  日期：2011.11.4

  Efficient and enantioselective: Using the iodine‐bridged dimeric iridium complex [Ir(H)[(S,S)‐(f)‐binaphane]}2(μ‐I)3]+I− (1) a wide range of tetrahydroisoquinoline alkaloids, including the substructure of the pharmaceutical drug solifenacin, were obtained with excellent enantioselectivities and high turnover numbers (see scheme).

  高效和对映选择性：使用碘桥接的二聚体铱络合物[的Ir（H）[（小号，小号） - （F）-binaphane]} 2（μ-I）3 ] +我- （1）广泛的获得了四氢异喹啉碱生物碱，包括药物索非那新的亚结构，具有出色的对映选择性和高周转率（参见方案）。
• Pharmaceutical tetrahydroisoquinolines
  申请人：John Wyeth & Brother Limited

  公开号：US05118690A1

  公开（公告）日：1992-06-02

  The invention concerns a method for treating pain and/or CNS disorders characterized in that the method uses a compound which acts selectively as an antagonist of gamma aminobutyric acid (GABA) at GABA autoreceptors relative to GABA.sub.A receptors.

  这项发明涉及一种治疗疼痛和/或中枢神经系统疾病的方法，其特征在于该方法使用一种化合物，该化合物在GABA自受体相对于GABA.sub.A受体上选择性地作为γ-氨基丁酸（GABA）的拮抗剂。
• Studies on Cerebral Protective Agents. X. Synthesis and Evaluation of Anticonvulsant Activities for Novel 4,5,6,7-Tetrahydrothieno(3,2-c)pyridines and Related Compounds.
  作者：Mitsuru OHKUBO、Atsuchi KUNO、Kiyotaka KATSUYA、Yoshiko UEDA、Kiyoharu SHIRAKAWA、Hajime NAKANISHI、Takayoshi KINOSHITA、Hisashi TAKASUGI

  DOI：10.1248/cpb.44.778

  日期：——

  1-thienyl-1,2,3,4-tetrahydroisoquinolines and related compounds, in which the benzene rings of (+)-1 (FR115427) were replaced with heteroaromatic rings such as thiophene, furan, benzothiophene and indole, were synthesized and evaluated for anticonvulsant activity against i.c.v. N-methyl-D-aspartate (NMDA)-induced seizures in mice. Among these compounds, (+)-4-methyl-4-phenyl-4,5,6,7-tetrahydrothieno[3

  新型4,5,6,7-四氢噻吩并[3,2-c]吡啶，1-噻吩基-1,2,3,4-四氢异喹啉和相关化合物，其中（+）-1的苯环（FR115427）用杂芳环如噻吩，呋喃，苯并噻吩和吲哚取代，合成并评估其对小鼠ICV N-甲基-D-天冬氨酸（NMDA）诱导的癫痫的抗惊厥活性。在这些化合物中，（+）-4-甲基-4-苯基-4,5,6,7-四氢噻吩并[3,2-c]吡啶盐酸盐（（+）-2a），（+）-4-甲基- 4-（2-噻吩基）-4,5,6,7-四氢噻吩并[3,2-c]吡啶盐酸盐（（+）-2g）和（-）1-甲基-2-（2-噻吩基）- 1,2,3,4-四氢异喹啉盐酸盐（（-）-3a）显示出显着的抗惊厥活性。讨论了与该系列化合物的抗惊厥活性有关的构效关系。
• The first example of an intramolecular Diels–Alder furan (IMDAF) reaction of iminium salts and its application in a short and simple synthesis of the isoindolo[1,2-a]isoquinoline core of the jamtine and hirsutine alkaloids
  作者：Fedor I. Zubkov、Julya D. Ershova、Vladimir P. Zaytsev、Mykola D. Obushak、Vasyl S. Matiychuk、Ekaterina A. Sokolova、Victor N. Khrustalev、Alexey V. Varlamov

  DOI：10.1016/j.tetlet.2010.10.046

  日期：2010.12

  1-(2-Furyl)-3,4-dihydroisoquinolines, easily prepared from readily available phenethylamines, undergo tandem alkylation/[4+2]-cycloaddition with allyl halides. The reaction proceeds via 2-allyl-1-furyl-3,4-dihydroisoquinolinium salt formation and subsequent intramolecular exo-Diels–Alder reaction of furan with the allyl fragment (IMDAF reaction). The adducts formed include the basic structural element

  1-（2-呋喃基）-3,4-二氢异喹啉很容易从容易获得的苯乙胺制备，并与烯丙基卤化物一起进行串联烷基化/ [4 + 2]-环加成反应。通过2-烯丙基-1-呋喃基-3,4-二氢异喹啉盐形成和随后的分子内反应进行外切与烯丙基片段（IMDAF反应）的呋喃-Diels-Alder反应。形成的加合物包括异吲哚并[1,2- a ]异喹啉碱生物碱和水苏碱的基本结构元素。
• Method of treatment and heterocyclic compounds used therein
  申请人：John Wyeth & Brother, Limited

  公开号：US05210088A1

  公开（公告）日：1993-05-11

  The invention concerns a method for treating pain and/or CNS disorders characterized in that the method uses a compound which acts selectively as an antagonist of gamma aminobutyric acid (GABA) at GABA autoreceptors relative to GABA.sub.A receptors.

  该发明涉及一种治疗疼痛和/或中枢神经系统疾病的方法，其特征在于该方法使用一种化合物，该化合物在GABA自主受体相对于GABA.sub.A受体上选择性地作为GABA的拮抗剂。