(S)-6,8-Dibromo-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid | 128502-57-8

• 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: (S)-6,8-Dibromo-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid
• 英文别名: (3S)-6,8-Dibromo-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
• CAS: 128502-57-8
• 化学式: C₁₀H₉Br₂NO₃
• 分子量: 350.994
• InChiKey: XPMBWJUCEIXOBO-ZETCQYMHSA-N

物化性质

• 沸点：
  457.1±45.0 °C(Predicted)
• 密度：
  2.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-6,8-Dibromo-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid 在 四(三苯基膦)钯 、 sodium hydride 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  Novel Dmt-Tic dipeptide analogues as selective delta-opioid receptor antagonists

  摘要：

  A series of Dmt-Tic analogues with substitution on the Tic aromatic ring has been synthesized and evaluated for opioid receptor affinity and activation. Incorporation of large hydrophobic groups at position 7 of Tic did not greatly alter the delta opioid receptor binding affinities of the dipeptides whereas substitution at position 6 substantially diminished their affinity. These modified Dmt-Tic peptides showed binding affinities as low as 2.5 nM with up to 500-fold selectivity for the delta versus mu opioid receptor and proved to be 6 receptor antagonists. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00652-6
• 作为产物：
  描述：

  L-7-羟基-1,2,3,4-四氢异喹啉-3-羧酸 在 溴 、 溶剂黄146 作用下， 生成 (S)-6,8-Dibromo-1,2,3,4-tetrahydro-7-hydroxy-isoquinoline-3-carboxylic acid 、 (3S)-6-bromo-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Novel Dmt-Tic dipeptide analogues as selective delta-opioid receptor antagonists

  摘要：

  A series of Dmt-Tic analogues with substitution on the Tic aromatic ring has been synthesized and evaluated for opioid receptor affinity and activation. Incorporation of large hydrophobic groups at position 7 of Tic did not greatly alter the delta opioid receptor binding affinities of the dipeptides whereas substitution at position 6 substantially diminished their affinity. These modified Dmt-Tic peptides showed binding affinities as low as 2.5 nM with up to 500-fold selectivity for the delta versus mu opioid receptor and proved to be 6 receptor antagonists. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00652-6

文献信息

• A Facile Synthesis of 1,2,3,4-Tetrahydro-7-hydroxyisoquinoline-3-carboxylic Acid, a Conformationally Constrained Tyrosine Analogue
  作者：Kris Verschueren、Géza Toth、Dirk Tourwé、Michal Lebl、Georges Van Binst、Victor Hruby

  DOI：10.1055/s-1992-26135

  日期：——

  A rapid synthesis of 1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid is given. Pictet-Spengler reaction on diiodo- or dibromo-substituted tyrosine (3-(3,5-dihalo-4-hydroxyphenyl)-2-aminopropanoic acid), followed by catalytic dehalogenation gives the desired compound in high optical purity.

  给出了1,2,3,4-四氢-7-羟基异喹啉-3-羧酸的快速合成方法。在二碘或二溴取代的酪氨酸（3-(3,5-二卤-4-羟基苯基）-2-氨基丙酸）上进行 Pictet-Spengler 反应，然后催化脱卤，得到高光学纯度的所需化合物。