异丙基肾上腺酮 | 121-28-8

• 物质功能分类: 原料药 - 激素及调节内分泌功能类药
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 异丙基肾上腺酮
• 中文别名: 1-(3,4-二羟基苯基)-2-[(1-甲基乙基)氨基]-1-乙酮；1-(3,4-二羟基苯基)-2-[(1-甲基乙基)氨基]乙酮；(3,4-二羟基苯基)[(异丙基氨基)甲基]酮；1-(3,4-二羟基苯基)-2-(异丙基氨基)乙酮
• 英文名称: Isoproterenon
• 英文别名: 3,4-Dihydroxy-α-isopropylaminoacetophenon；4-(Isopropylaminoacetyl)-brenzcatechin；Isoproterenone；1-(3,4-dihydroxy-phenyl)-2-isopropylamino-ethanone；1-(3,4-dihydroxyphenyl)-2-[(1-methylethyl)amino]ethan-1-one；1-(3,4-Dihydroxy-phenyl)-2-isopropylamino-aethanon；1-(3,4-dihydroxyphenyl)-2-(propan-2-ylamino)ethanone
• CAS: 121-28-8
• 化学式: C₁₁H₁₅NO₃
• mdl: MFCD01037086
• 分子量: 209.245
• InChiKey: BIQMIYWSZZTXEX-UHFFFAOYSA-N

物化性质

• 熔点：
  96℃
• 密度：
  1.185±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

制备方法与用途

化学性质：黄色结晶。

用途：作为异丙基肾上腺素（喘息定）的中间体。

生产方法：通过在氧氯化磷作用下，使邻苯二酚与氯乙酸反应生成4-（氯乙酰基）邻苯二酚，再以异丙胺进行胺化制得。

反应信息

• 作为反应物：
  描述：

  异丙基肾上腺酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以85.7%的产率得到盐酸异丙肾上腺素
  参考文献：
  名称：

  一种异丙肾上腺素硫酸盐的制备方法

  摘要：

  本发明公开了一种异丙肾上腺素硫酸盐的制备方法，包括下列步骤：（1）在室温下，异丙肾上腺素酮体在甲醇的溶剂里与硼氢化钠作用下经加氢还原得到异丙肾上腺素；（2）负压浓缩完溶剂甲醇，加入水之后，再用乙酸乙酯萃取，用60%硫酸调体系pH值至酸性，之后升温至回流30分钟溶清；（3）冷冻过夜，得到白色粉状结晶；（4）过滤，洗涤后烘干，再用乙醇重结晶得到异丙肾上腺素硫酸盐；本发明规避了高压加氢的危险隐患，采用硼氢化钠还原使反应更加安全；采用常压反应，避免使用金属高压反应釜；原料易得，工艺简单合理。

  公开号：

  CN107382750B
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 盐酸 作用下， 生成 异丙基肾上腺酮
  参考文献：
  名称：

  Moed et al., Recueil des Travaux Chimiques des Pays-Bas, 1952, vol. 71, p. 933,940

  摘要：

  DOI：

文献信息

• [EN] PROCESS FOR PREPARATION OF ISOPROTERENOL HYDROCHLORIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CHLORHYDRATE D'ISOPROTÉRÉNOL
  申请人：EMCURE PHARMACEUTICALS LTD

  公开号：WO2018127806A1

  公开（公告）日：2018-07-12

  The present invention provides a process for preparation of isoproterenol hydrochloride (1a) comprising catalytic hydrogenation of 3',4'-dihydroxy-2-(isopropylamino)-acetophenone hydrochloride (5a) in presence of an ion exchange resin, to provide isoproterenol hydrochloride (1a).

  本发明提供了一种制备异丙肾上腺素盐酸盐（1a）的方法，包括在离子交换树脂的存在下，对3'，4'-二羟基-2-（异丙基氨基）-乙酰苯酮盐酸盐（5a）进行催化氢化，以提供异丙肾上腺素盐酸盐（1a）。
• Process for reducing blood pressure and blocking .beta.-adrenergic
  申请人：Kyowa Hakko Kogyo Co., Ltd.

  公开号：US04147799A1

  公开（公告）日：1979-04-03

  Ethanolamine derivatives and their acid addition salts are prepared (1) by reacting a 1-(3,4-methylenedioxyphenyl)-2-aminoethanol compound or an .alpha.-amino-(3,4-methylenedioxy)acetophenone compound with an alkanal or an alkanone under reduction conditions, (2) by hydrogenating and/or hydrogenolyzing a 1-(3,4-methylenedioxyphenyl)-2-(N-substituted amino)-ethanol compound or an .alpha.-(N-substituted amino)-(3,4-methylenedioxy)acetophenone compound, and (3) by reacting a (3,4-methylenedioxyphenyl)-ethylene oxide compound or a 1-(3,4-methylenedioxyphenyl)-2-substituted ethanol compound with an amine. The ethanolamine derivatives and their salts show .beta.-adrenergic receptor blocking activity, and are expected to be useful in the treatment of heart disease, hypertension, myocardites and pheochromocytoma.

  乙醇胺衍生物及其酸盐可以通过以下方法制备：(1)通过在还原条件下将1-(3,4-二甲氧基苯基)-2-氨基乙醇化合物或α-氨基-(3,4-二甲氧基)乙酮化合物与烷醛或烷酮反应，(2)通过氢化和/或氢解1-(3,4-二甲氧基苯基)-2-(N-取代氨基)-乙醇化合物或α-(N-取代氨基)-(3,4-二甲氧基)乙酮化合物，(3)通过将(3,4-二甲氧基苯基)-乙烯氧化物或1-(3,4-二甲氧基苯基)-2-取代乙醇化合物与胺反应。乙醇胺衍生物及其盐具有β-肾上腺素能受体阻滞活性，预计可用于治疗心脏病、高血压、心肌炎和嗜铬细胞瘤。
• CATECHOLAMINE DERIVATIVES FOR OBESITY AND NEUROLOGICAL DISORDERS
  申请人：Ye Keqiang

  公开号：US20120022086A1

  公开（公告）日：2012-01-26

  Novel compounds, compositions, and methods related to the activation of the TrkB receptor are provided. The methods include administering in vivo or in vitro a therapeutically effective amount of a compound containing a catecholamine backbone and pharmaceutically acceptable salts, prodrugs, and derivatives thereof. Specifically, methods, compositions, and compounds for the treatment of disorders including neurological disorders, neuropsychiatric disorders, and metabolic disorders are provided. For example, a first method is provided of treating or reducing the risk of depression, anxiety, or obesity in a subject, which includes administering to the subject a therapeutically effective amount of the described compounds. A further method of promoting neuroprotection in a subject also is provided, which includes administering to the subject a therapeutically effective amount of the described compounds.

  提供了与TrkB受体激活相关的新型化合物、组合物和方法。这些方法包括在体内或体外给予含有儿茶酚背骨和药学上可接受的盐、前药和衍生物的化合物的治疗有效量。具体提供了用于治疗神经系统疾病、神经精神疾病和代谢性疾病的方法、组合物和化合物。例如，提供了一种用于治疗或减少受试者抑郁、焦虑或肥胖风险的第一种方法，其中包括向受试者给予所述化合物的治疗有效量。还提供了一种促进受试者神经保护的方法，其中包括向受试者给予所述化合物的治疗有效量。
• Process for preparation of isoproterenol hydrochloride
  申请人：EMCURE PHARMACEUTICALS LIMITED

  公开号：US10759738B2

  公开（公告）日：2020-09-01

  The present invention provides a process for preparation of isoproterenol hydrochloride (1a) comprising catalytic hydrogenation of 3′,4′-dihydroxy-2-(isopropylamino)-acetophenone hydrochloride (5a) in presence of an ion exchange resin, to provide isoproterenol hydrochloride (1a).

  本发明提供了一种制备盐酸异丙肾上腺素（1a）的工艺，包括在离子交换树脂存在下，催化加氢3′，4′-二羟基-2-（异丙基氨基）-苯乙酮盐酸盐（5a），得到盐酸异丙肾上腺素（1a）。
• Purification and characterization of a novel carbonyl reductase involved in oxidoreduction of aromatic β-amino ketones/alcohols
  作者：Shengbin He、Zhenshou Wang、Yang Zou、Shaofang Chen、Xiaoping Xu

  DOI：10.1016/j.procbio.2014.03.023

  日期：2014.7

  Aromatic beta-amino ketones/alcohols such as adrenalone play an important role in some stereoselective synthesis of pharmaceuticals. Unfortunately, the transformation of aromatic beta-amino ketones to their chiral alcohols has been carried out chemically as no corresponding biocatalyst has been available. Here, a novel carbonyl reductase responsible for the reduction of adrenalone to (R)-(-)-epinephrine was identified and characterized from Kocuria rhizophila. This enzyme was purified to homogeneity by ammonium sulfate precipitation followed by ion-exchange column chromatography, hydrophobic chromatography and gel chromatography. The purified enzyme yielded pure (R)-enantiomer product with high activity and utilized NADH as the cofactor. The enzyme had special significance by showing selectivity for many aromatic beta-amino ketones/alcohols such as 2-amino-acetophenone, 2-amino-4'-hydroxyacetophenone, isoproterenol and ephedrine. The maximum reaction rate (V-max) and apparent Michaelis-Menten constant (K-m) for adrenalone and NADH were 14.62 mu mol/(min mg) protein and 0.189 mM, 11.66 mu mol/(min mg) protein and 0.204 mM respectively. These properties ensure the enzyme a promising future for industrial application as a replacement of chemical synthesis of aromatic beta-amino chiral alcohols. (C) 2014 Elsevier Ltd. All rights reserved.