6-methoxy-7-hydroxy-2,3-dihydroindole | 70837-64-8

• 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-hydroxy-2,3-dihydroindole
• 英文别名: 7-hydroxy-6-methoxyindoline；6-Methoxyindolin-7-ol；6-methoxy-2,3-dihydro-1H-indol-7-ol
• CAS: 70837-64-8
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: LXOHYZHLGHTTOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-7-hydroxy-2,3-dihydroindole 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丁醇 、 二甲基亚砜 为溶剂， 反应 37.25h， 生成 (S)-2-[((2-(N-Cbz)-(6-methoxy-2,3-dihydro-7-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 、 5%-palladium/activated carbon 、 氢气 、 三氯化硼 、 potassium carbonate 、 溶剂黄146 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 30.5h， 生成 6-methoxy-7-hydroxy-2,3-dihydroindole
  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

• COMPOSITION TINCTORIALE A BASE DE DERIVES D'HYDROXYINDOLINE
  申请人：L'OREAL

  公开号：EP0603322A1

  公开（公告）日：1994-06-29
• [EN] DYEING COMPOSITION BASED ON HYDROXYINDOLINE DERIVATIVES
  申请人：L'OREAL

  公开号：WO1993005018A1

  公开（公告）日：1993-03-18

  (EN) The use of a hydroxyindoline derivative of formula (I), wherein R1 is hydrogen or C1-4 alkyl; R2 is hydrogen or C1-4 alkyl; OH and -OR2 are in positions 4, 5, 6 or 7, with the proviso that when they are in positions 5 and 6, R2 is alkyl; and acid addition salts thereof; for dyeing keratin-containing matter, particularly human keratin-containing matter, is described.(FR) L'invention est relative à l'utilisation pour la teinture des matières kératiniques, en particulier les matières kératiniques humaines, d'un dérivé d'hydroxyindoline répondant à la formule (I), dans laquelle: R1 représente un hydrogène ou un alkyle en C1-C4; R2 représente un hydrogène ou un alkyle en C1-C4; OH et -OR2 occupent les positions 4, 5, 6 ou 7, sous réserve que lorsqu'ils occupent les positions 5 et 6, R2 désigne alkyle; ainsi que leurs sels d'addition d'acides.
• [EN] DYE COMPOSITION USING A (HYDROXY)INDOLINE COUPLER IN A MEDIUM RICH IN FATTY SUBSTANCES, PROCESS AND DEVICES<br/>[FR] COMPOSITION DE COLORATION UTILISANT UN COUPLEUR (HYDROXY)INDOLINE DANS UN MILIEU RICHE EN SUBSTANCES GRASSES, PROCÉDÉ ET DISPOSITIF
  申请人：OREAL

  公开号：WO2012163898A1

  公开（公告）日：2012-12-06

  The present invention relates to a composition for dyeing keratin fibres, comprising: at least one fatty substance, at least one surfactant; at least one oxidation base, at least one indoline coupler of formula (B7) or of formula (B8), and also salts thereof, optical and geometrical isomers and tautomers thereof, and hydrates thereof, formulae (B7) and (B8) being the following: at least one basifying agent; the fatty substance content representing in total at least 25% by weight relative to the total weight of the composition; at least one oxidation base being chosen from heterocyclic oxidation bases when the coupler is of formula (B7). The present invention also relates to a process using this composition in the presence of at least one chemical oxidizing agent, and to multi-compartment devices suitable for the implementation of the invention.
• 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
  作者：Laura Fumagalli、Marco Pallavicini、Roberta Budriesi、Cristiano Bolchi、Mara Canovi、Alberto Chiarini、Giuseppe Chiodini、Marco Gobbi、Paola Laurino、Matteo Micucci、Valentina Straniero、Ermanno Valoti

  DOI：10.1021/jm400867d

  日期：2013.8.22

  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.