6-fluoropropoxytetrahydroisoquinoline | 1063704-81-3

• 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: 6-fluoropropoxytetrahydroisoquinoline
• 英文别名: 6-(3-Fluoropropoxy)-1,2,3,4-tetrahydroisoquinoline；6-(3-fluoropropoxy)-1,2,3,4-tetrahydroisoquinoline
• CAS: 1063704-81-3
• 化学式: C₁₂H₁₆FNO
• 分子量: 209.264
• InChiKey: PNOSOFCPKLLEKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-fluoropropoxytetrahydroisoquinoline 、 4-(5-cyano-1H-indol-3-yl)-cyclohexanone 在 三乙酰氧基硼氢化钠 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 生成 C₂₇H₃₀FN₃O 、 cis-3-(4-(6-(3-fluoropropoxy)-3,4-dihydroisoquinolin-2(1H)-yl)cyclohexyl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  3-(4-(6-Fluoroalkoxy-3,4-dihydroisoquinoline-2(1H)-yl)cyclohexyl)-1H-indole-5-carbonitriles for SERT imaging: Chemical synthesis, evaluation in vitro and radiofluorination

  摘要：

  Aminocyclohexyl indoles bind with high affinity and specificity toward the serotonin transporter (SERT). Based on this structural lead, we designed fluoroalkoxydihydroisoquinoline-cyclohexyl indole carbonitriles for future application as F-18-labeled tracers for SERT imaging by PET. Six compounds, three pairs of cis- and trans-isomer derivatives, respectively, were synthesized and evaluated in vitro. The chemistry of the new compounds, their affinity and specificity data, the general route to the phenolic precursor for labeling, and the successful F-18-fluoroalkylation of one pair of compounds are described herein. (C) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.077
• 作为产物：
  描述：

  6-(3-fluoropropoxy)-3,4-dihydroisoquinolin-1(2H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以90%的产率得到6-fluoropropoxytetrahydroisoquinoline
  参考文献：
  名称：

  3-(4-(6-Fluoroalkoxy-3,4-dihydroisoquinoline-2(1H)-yl)cyclohexyl)-1H-indole-5-carbonitriles for SERT imaging: Chemical synthesis, evaluation in vitro and radiofluorination

  摘要：

  Aminocyclohexyl indoles bind with high affinity and specificity toward the serotonin transporter (SERT). Based on this structural lead, we designed fluoroalkoxydihydroisoquinoline-cyclohexyl indole carbonitriles for future application as F-18-labeled tracers for SERT imaging by PET. Six compounds, three pairs of cis- and trans-isomer derivatives, respectively, were synthesized and evaluated in vitro. The chemistry of the new compounds, their affinity and specificity data, the general route to the phenolic precursor for labeling, and the successful F-18-fluoroalkylation of one pair of compounds are described herein. (C) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.077

文献信息

• [EN] TETRAHYDROISOQUINOLINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS USEFUL FOR THE TREATMENT OF OBESITY AND DIABETES<br/>[FR] DÉRIVÉS DE TÉTRAHYDROISOQUINOLINE ET COMPOSITIONS PHARMACEUTIQUES UTILES POUR LE TRAITEMENT DE L'OBÉSITÉ ET DU DIABÈTE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2016041845A1

  公开（公告）日：2016-03-24

  The invention relates to new pyrrolidine derivatives of the formula wherein R1 to R6, n and m are as defined in the description and claims, to their use as medicaments, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  该发明涉及新的吡咯烷衍生物，其化学式中的R1至R6、n和m如描述和索赔中所定义，用作药物，用于它们的治疗用途的方法，以及含有它们的药物组合物。
• Tetrahydroisoquinoline derivatives, pharmaceutical compositions and uses thereof
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20160075657A1

  公开（公告）日：2016-03-17

  The invention relates to new pyrrolidine derivatives of the formula wherein R 1 to R 6 , n and m are as defined in the description and claims, to their use as medicaments, to methods for their therapeutic use and to pharmaceutical compositions containing them.

  本发明涉及新的吡咯烷衍生物，其化学式如下：其中R1至R6，n和m的定义如说明书和权利要求书中所述，以及它们作为药物的用途，它们的治疗用途的方法以及包含它们的制药组合物。
• TETRAHYDROISOQUINOLINE DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS USEFUL FOR THE TREATMENT OF OBESITY AND DIABETES
  申请人：Boehringer Ingelheim International GmbH

  公开号：EP3194367B1

  公开（公告）日：2021-08-18
• US9340510B2
  申请人：——

  公开号：US9340510B2

  公开（公告）日：2016-05-17
• 3-(4-(6-Fluoroalkoxy-3,4-dihydroisoquinoline-2(1H)-yl)cyclohexyl)-1H-indole-5-carbonitriles for SERT imaging: Chemical synthesis, evaluation in vitro and radiofluorination
  作者：Uta Funke、Steffen Fischer、Achim Hiller、Matthias Scheunemann、Winnie Deuther-Conrad、Peter Brust、Jörg Steinbach

  DOI：10.1016/j.bmcl.2008.06.077

  日期：2008.8

  Aminocyclohexyl indoles bind with high affinity and specificity toward the serotonin transporter (SERT). Based on this structural lead, we designed fluoroalkoxydihydroisoquinoline-cyclohexyl indole carbonitriles for future application as F-18-labeled tracers for SERT imaging by PET. Six compounds, three pairs of cis- and trans-isomer derivatives, respectively, were synthesized and evaluated in vitro. The chemistry of the new compounds, their affinity and specificity data, the general route to the phenolic precursor for labeling, and the successful F-18-fluoroalkylation of one pair of compounds are described herein. (C) 2008 Elsevier Ltd. All Fights reserved.