4,5-dimethoxy-2-aminoindan hydrochloride | 37096-37-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4,5-dimethoxy-2-aminoindan hydrochloride
• 英文别名: 4,5-dimethoxy-2,3-dihydro-1H-inden-2-amine;hydrochloride
• CAS: 37096-37-0
• 化学式: C₁₁H₁₅NO₂*ClH
• 分子量: 229.707
• InChiKey: YRJOTRQHIJCAQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.55
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxy-2-aminoindan hydrochloride 在 氢溴酸 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 为溶剂， 反应 53.0h， 生成 N-[2-(methyl-ethyl)]-4,5-dihydroxy-2-aminoindan hydrobromide
  参考文献：
  名称：

  Perez, Julio A.; Dominguez, Jose N.; Angel, Jorge E., Arzneimittel-Forschung/Drug Research, 1997, vol. 47, # 11, p. 1208 - 1210

  摘要：

  DOI：
• 作为产物：
  描述：

  2-amino-4,5-dimethoxy-1-indanol hydrochloride 在 palladium on activated charcoal 高氯酸 、 氢气 作用下， 以 溶剂黄146 为溶剂， 70.0 ℃ 、275.55 kPa 条件下， 反应 18.0h， 以66%的产率得到4,5-dimethoxy-2-aminoindan hydrochloride
  参考文献：
  名称：

  2-氨基-1-茚满酮还原反应中羰基的异常转位

  摘要：

  2-氨基-4,5-二甲氧基-1-茚满酮盐酸盐的催化还原过程得到2-氨基-4,5-二甲氧基茚满盐酸盐的主要还原产物，以及少量重排的4,5-二甲氧基茚满酮- 2-茚满酮。分离的中间体 2-氨基-4,5-二甲氧基-1-茚满醇盐酸盐在催化反应条件下（酸处理）仅产生 4,5-二甲氧基-2-茚满酮。根据红外、核磁共振和元素分析的结果验证了不寻常的转化产物。讨论了一种可能的重排机制。

  DOI：

  10.1246/bcsj.54.3197

文献信息

• Process for the preparation of arylalkylamines and substituted
  申请人：Hoechst Celanese Corporation

  公开号：US05041669A1

  公开（公告）日：1991-08-20

  Arylalkylamines (as a sulfate salt) e.g. tyramine sulfate, are prepared by reacting substituted or unsubstituted arylalkylketones with a lower alkylnitrite in the presence of hydrogen chloride in a dipolar aprotic solvent, then combining the reaction mixture with water and extracting it with a lower alkyl ester or alcohol to recover an aryl-.alpha.-oximinoalkylketone extract. The extract, combined with a supported hydrogenation catalyst (e.g. palladium on carbon) in a nonaqueous reaction medium of a major proportion of a mildly protic carboxylic acid (e.g. acetic acid) and a minor proportion of a strong inorganic acid (e.g. sulfuric acid), which is effective in the presence of the catalyst for secondary alcohol dehydration and active as an absorbant for water produced in the dehydration reaction, is hydrogenated to produce the arylalkylamine sulfate sale.

  芳基烷基胺（作为硫酸盐）例如酪胺硫酸盐，是通过在双极性无质子溶剂中，在氢氯酸的存在下，将取代或未取代的芳基烷基酮与较低的烷基亚硝酸盐反应，然后将反应混合物与水混合，并用较低的烷基酯或醇提取它以回收芳基-α-肟基烷基酮提取物制备的。将提取物与支持的氢化催化剂（例如碳上的钯）结合在非水反应介质中，该介质包括主要比例的温和质子性羧酸（例如乙酸）和少量强无机酸（例如硫酸），对于二级醇脱水反应具有有效的催化作用，并且作为脱水反应中产生的水的吸收剂，经过氢化反应，产生芳基烷基胺硫酸盐的销售。
• Process for the preparation of arylalkylamines and substituted arylalkylamines
  申请人：HOECHST CELANESE CORPORATION

  公开号：EP0481705A1

  公开（公告）日：1992-04-22

  Arylalkylamines (as a sulfate salt) e.g. tyramine sulfate, are prepared by reacting substituted or unsubstituted arylalkylketones with a lower alkylnitrite in the presence of hydrogen chloride in a dipolar aprotic solvent, then combining the reaction mixture with water and extracting it with a lower alkyl ester or alcohol to recover an aryl-α-oximinoalkylketone extract. The extract, combined with a supported hydrogenation catalyst (e.g. palladium on carbon) in a nonaqueous reaction medium of a major proportion of a mildly protic carboxylic acid (e.g. acetic acid) and a minor proportion of a srong inorganic acid (e.g. sulfuric acid), which is effective in the presence of the catalyst for secondary alcohol dehydration and active as an absorbant for water produced in the dehydration reaction, is hydrogenated to produce the arylalkylamine sulfate sale.

  芳烷基胺（作为硫酸盐），例如硫酸酪胺，是通过在氯化氢存在下，在二极性非 普罗溶剂中，使取代或未取代的芳烷基酮与低级亚硝酸烷基酯反应，然后将反应混 合物与水混合，并用低级烷基酯或醇萃取，以回收芳基-α-氧亚氨基烷基酮萃取物。该萃取物与支撑氢化催化剂（如碳上钯）在非水反应介质中结合，该反应介质主要成分为轻度质子羧酸（如乙酸），次要成分为强无机酸（如硫酸），在催化剂存在下，强无机酸对二次醇脱水有效，对脱水反应中产生的水有吸附作用，氢化反应生成出售的芳基烷基胺硫酸盐。
• Conformationally restricted congeners of dopamine derived from 2-aminoindan
  作者：Joseph G. Cannon、Julio A. Perez、Ranbir K. Bhatnagar、John Paul Long、Fouad M. Sharabi

  DOI：10.1021/jm00354a010

  日期：1982.12

  Two series of N-substituted 2-aminoindan systems have been prepared: 4,5-dihydroxy-2-aminoindan (1) has a hydroxylation pattern analogous to the alpha conformer of dopamine, and 5,6-dihydroxy-2-aminoindan (2) has a hydroxylation pattern of the beta conformer of dopamine. All members of both series demonstrated only extremely weak binding to calf caudate homogenate. Certain N-alkylated 4,5-dihydroxyindans were violent emetics in the dog and were potent in blockade of the effect of stimulation of the cardioaccelerator nerve of the cat. In contrast, the 5,6-dihydroxy series displayed low or no activity/potency in these assays. Conformational analysis of the 2-aminoindan system is described and discussed.
• Synthesis, dopaminergic profile, and molecular dynamics calculations of N-aralkyl substituted 2-aminoindans
  作者：Sebastian A. Andujar、Biagina Migliore de Angel、Jaime E. Charris、Anita Israel、Heberto Suárez-Roca、Simon E. López、Maria R. Garrido、Elvia Victoria Cabrera、Gonzalo Visbal、Cecire Rosales

  DOI：10.1016/j.bmc.2007.12.027

  日期：2008.3.15

  Brain dopaminergic system has a crucial role in the etiology of several neuropsychiatric disorders, including Parkinson's disease, depression, and schizophrenia. Several dopaminergic drugs are used to treat these pathologies, but many problems are attributed to these therapies. Within this context, the search for new more efficient dopaminergic agents with less adverse effects represents a vast research field. The aim of the present study was to synthesize N-[2-(4,5-dihydroxyphenyl)-methyl-ethyl]-4,5-dihydroxy-2-aminoindan hydrobromide (3), planned to be a dopamine ligand, and to evaluate its dopaminergic action profile. This compound was assayed as a diastereoisomeric mixture in two experimental models: stereotyped behavior (gnaw) and renal urinary response, after central administration. The pharmacological results showed that compound 3 significantly blocked the apomorphine-induced stereotypy and dopamine-induced diuresis and natriuresis in rats. Thus, compound 3 demonstrated an inhibitory effect on dopaminergic-induced behavior and renal action. N-[2-(-Methyl-ethyl)]-4,5-dihydroxy-2-aminoindan hydrobromide (4) was previously reported as an inotropic agent, and in the present work it was also re-evaluated as a diastereoisomeric mixture for its possible central action on the behavior parameters such as stereotypy and dopamine-induced diuresis and natriuresis in rats. Our results indicate that compound 4 produces an agonistic response, possibly through dopaminergic mechanisms. To better understand the experimental results we performed molecular dynamics simulations of two complexes: compound 3/D(2)DAR (dopamine receptor) and compound 4/D(2)DAR. The differential binding mode obtained for these complexes could explain the antagonist and agonist activity obtained for compounds 3 and 4, respectively. (C) 2007 Elsevier Ltd. All rights reserved.
• US5041669A
  申请人：——

  公开号：US5041669A

  公开（公告）日：1991-08-20