6-methoxy-7-hydroxyindole | 70837-63-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6-methoxy-7-hydroxyindole
• 英文别名: 6-methoxyindol-7-ol；6-methoxy-indol-7-ol；7-hydroxy-6-methoxyindole；6-methoxy-1H-indol-7-ol
• CAS: 70837-63-7
• 化学式: C₉H₉NO₂
• 分子量: 163.176
• InChiKey: DUTPCDNXEGOXCZ-UHFFFAOYSA-N

物化性质

• 熔点：
  89 °C
• 沸点：
  359.9±22.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  45.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methoxy-7-hydroxyindole 在 吡啶 、 5%-palladium/activated carbon 、 氢气 、 sodium hydride 、 potassium carbonate 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 异丁醇 、 二甲基亚砜 为溶剂， 反应 36.75h， 生成 (S)-2-[((2-(6-methoxy-2,3-dihydro-6-indolyloxy)ethyl)amino)methyl]-1,4-benzodioxane
  参考文献：
  名称：

  6-Methoxy-7-benzofuranoxy and 6-Methoxy-7-indolyloxy Analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a Potent and Selective α_1D-Adrenoceptor Antagonist

  摘要：

  Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, alpha(1)-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclo-hexane, or especially by ortho,meta-fused benzene preferentially elicits alpha(1D)-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho hetero-disubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest alpha(1D)-AR antagonist affinity (pA(2) 9.58) with significant alpha(1D)/alpha(1A) and alpha(1D)/alpha(1B) selectivity. In addition, compared both to alpha(1D)-AR antagonists structurally related to 1 and to the well-known alpha(1D)-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral alpha(1)-AR antagonist behavior.

  DOI：

  10.1021/jm400867d
• 作为产物：
  描述：

  2,3-二甲氧基苯甲酸 在 sodium tetrahydroborate 、 叠氮磷酸二苯酯 、 三氯化硼 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 水 、 1,2-二氯乙烷 为溶剂， 反应 13.0h， 生成 6-methoxy-7-hydroxyindole
  参考文献：
  名称：

  6-Methoxy-7-benzofuranoxy and 6-Methoxy-7-indolyloxy Analogues of 2-[2-(2,6-Dimethoxyphenoxy)ethyl]aminomethyl-1,4-benzodioxane (WB4101):1 Discovery of a Potent and Selective α_1D-Adrenoceptor Antagonist

  摘要：

  Previous results have shown that replacement of one of the two o-methoxy groups at the phenoxy residue of the potent, but not subtype-selective, alpha(1)-AR antagonist (S)-WB4101 [(S)-1] by phenyl, or by ortho,meta-fused cyclo-hexane, or especially by ortho,meta-fused benzene preferentially elicits alpha(1D)-AR antagonist affinity. Such observations inspired the design of four new analogues of 1 bearing, in lieu of the 2,6-dimethoxyphenoxy residue, a 6-methoxy-substituted 7-benzofuranoxy or 7-indolyloxy group or, alternatively, their corresponding 2,3-dihydro form. Of these new compounds, which maintain, rigidified, the characteristic ortho hetero-disubstituted phenoxy substructure of 1, the S enantiomer of the dihydrobenzofuranoxy derivative exhibited the highest alpha(1D)-AR antagonist affinity (pA(2) 9.58) with significant alpha(1D)/alpha(1A) and alpha(1D)/alpha(1B) selectivity. In addition, compared both to alpha(1D)-AR antagonists structurally related to 1 and to the well-known alpha(1D)-AR antagonist BMY7378, this derivative had modest 5-HT1A affinity and neutral alpha(1)-AR antagonist behavior.

  DOI：

  10.1021/jm400867d

文献信息

• Beer et al., Journal of the Chemical Society, 1951, p. 2029,2031
  作者：Beer et al.

  DOI：——

  日期：——
• Dharmasens, Priyanthi; Oliveira-Campos, Ana-M. R.; Queiroz, Maria-Joao R. P., Journal of Chemical Research, Miniprint, 1996, # 1, p. 316 - 363
  作者：Dharmasens, Priyanthi、Oliveira-Campos, Ana-M. R.、Queiroz, Maria-Joao R. P.、Shannon, Patric V. R.

  DOI：——

  日期：——
• Antimicrobial indolequinones from the mid-intestinal gland of the muricid gastropod Drupella fragum
  作者：Yoshiyasu Fukuyama、Chie Iwatsuki、Mitsuaki Kodama、Masamitsu Ochi、Kumi Kataoka、Kozo Shibata

  DOI：10.1016/s0040-4020(98)00593-6

  日期：1998.8

  Three new indolequinones, 6-merhoxyindole-4,7-quinone (1), 5-methoxyindole-4,7-quinone (2) and 5-methylindole-4,7-quinone (3) were isolated from the mid-intestinal gland of the muricid gastropod Drupella fragum. The structures of 1 and 2 were established by spectroscopic methods and total synthesis, whereas the structure of 3 was elucidated mainly by NMR spectroscopic analyses. Compounds 1 3 exhibited moderate antimicrobial activities against Staphylococcus aureus, Bacillus subtilis, and Escherichia coli with MIC = 6.25 similar to 50 mu g/mL. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Iridium-Catalyzed C–H Borylation-Based Synthesis of Natural Indolequinones
  作者：Christy Wang、Jonathan Sperry

  DOI：10.1021/jo300330u

  日期：2012.3.16

  An iridium-catalyzed C-H borylation provides the key step in a short synthesis of two indolequinone natural products. This regioselective C-H functionalization strategy delivers 7-borylindoles that undergo facile oxidation hydrolysis to 7-hydroyindoles and subsequent oxidation to the desired indolequinones, thereby demonstrating a powerful application of the iridium-catalyzed C H borylation reaction. A significant result has arisen from the iridium-catalyzed borylation of N-diethylhydrosilyl-6-methoxyindole; even in the presence of a substituent at C6, the N-hydrosilyl group still directs borylation exclusively into the more sterically hindered C7 position in preference to C2.
• US5131911A
  申请人：——

  公开号：US5131911A

  公开（公告）日：1992-07-21