6-hydroxy-2,5,7,8-tetramethyl-2-(4-aminophenoxymethyl)chroman | 149695-61-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-hydroxy-2,5,7,8-tetramethyl-2-(4-aminophenoxymethyl)chroman
• 英文别名: 2-[(4-Aminophenoxy)methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol
• CAS: 149695-61-4
• 化学式: C₂₀H₂₅NO₃
• 分子量: 327.423
• InChiKey: NFWKKZJYMHRCPD-UHFFFAOYSA-N

物化性质

• 沸点：
  523.4±50.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(7-喹啉氧基)-2,3-环氧丙烷 、 6-hydroxy-2,5,7,8-tetramethyl-2-(4-aminophenoxymethyl)chroman 以 乙醇 为溶剂， 生成 2-[[4-[(2-Hydroxy-3-quinolin-7-yloxypropyl)amino]phenoxy]methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-ol
  参考文献：
  名称：

  New series of aryloxypropanolamines with both human β3-adrenoceptor agonistic activity and free radical scavenging properties

  摘要：

  A series of 13 novel hybrid molecules designed to possess both free radical scavenging activity and to stimulate the beta(3)-adrenoceptors in order to improve antidiabetic effect and to restore insulin sensitivity was synthesized and evaluated. Compounds were of quinolyl-, isoquinolyl-, pyridoindolyl- or carbazolyloxypropanolamine structure with a terminal amino group of benzopyranolyl-. di-tert-butylphenolyl- or methoxyindolyl- type. Some of the products possessed both the expected activities. (C) 2002 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0960-894x(01)00716-8
• 作为产物：
  描述：

  6-Hydroxy-2,5,7,8-tetramethyl-2-<(4-nitrophenoxy)methyl>chroman 在 镍 肼 作用下， 以 乙醇 为溶剂， 以100%的产率得到6-hydroxy-2,5,7,8-tetramethyl-2-(4-aminophenoxymethyl)chroman
  参考文献：
  名称：

  New series of aryloxypropanolamines with both human β3-adrenoceptor agonistic activity and free radical scavenging properties

  摘要：

  A series of 13 novel hybrid molecules designed to possess both free radical scavenging activity and to stimulate the beta(3)-adrenoceptors in order to improve antidiabetic effect and to restore insulin sensitivity was synthesized and evaluated. Compounds were of quinolyl-, isoquinolyl-, pyridoindolyl- or carbazolyloxypropanolamine structure with a terminal amino group of benzopyranolyl-. di-tert-butylphenolyl- or methoxyindolyl- type. Some of the products possessed both the expected activities. (C) 2002 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0960-894x(01)00716-8

文献信息

• Process for the preparation of
  申请人：Lonza Ltd.

  公开号：US05284961A1

  公开（公告）日：1994-02-08

  A novel process for the preparation of aminochromans of the general formula: ##STR1## wherein R is a lower alkyl group having 1 to 4 carbon atoms. In the process, nitrochromanones of the general formula: ##STR2## are reduced using zirconium oxide/isopropanol to give a mixture of a corresponding aminochromene: ##STR3## and a corresponding nitrochromene: ##STR4## The mixture is then hydrogenated with hydrogen in the presence of a hydrogenation catalyst to give the final product. The aminochromans are important intermediates for the preparation of hypolipidaemic pharmaceuticals.

  一种制备一般式为：##STR1##其中R是具有1到4个碳原子的低级烷基的氨基色酮的新工艺。在该工艺中，使用氧化锆/异丙醇还原一般式为：##STR2##的硝基色酮，以得到相应的氨基色酚和相应的硝基色酚的混合物。然后，在氢化催化剂的存在下，用氢气对混合物进行加氢，以得到最终产物。氨基色酮是制备降血脂药物的重要中间体。
• Verfahren zur Herstellung von 6-Hydroxy-2,5,7,8-tetraalkyl-2-(4-aminophenoxymethyl)chromanen
  申请人：LONZA AG

  公开号：EP0556830A1

  公开（公告）日：1993-08-25

  Es wird ein neues Verfahren zur Herstellung von Aminochromanen der allgemeinen Formel beschrieben. Dabei wird ein Nitrochromanon der allgemeinen Formel mit Wasserstoff in Gegenwart eines Hydrierkatalysators hydriert, das resultierende Aminochromanon (III) mit Zirkonoxid/Isopropanol zum Aminochromen (IV) reduziert und schliesslich mit Wasserstoff in Gegenwart eines Hydrierkatalysators zum Endprodukt hydriert. Die Aminochromane sind wertvolle Zwischenprodukte zur Herstellung lipidsenkender Pharmazeutika.

  一种制备通式氨基色素的新工艺 的新工艺。在该工艺中，通式为 在氢化催化剂存在下用氢气氢化，得到的氨基色满酮 (III) 用氧化锆/异丙醇还原成氨基色满 (IV)，最后在氢化催化剂存在下用氢气氢化得到最终产品。 氨基色烷是生产降血脂药物的重要中间体。
• US5310952A
  申请人：——

  公开号：US5310952A

  公开（公告）日：1994-05-10
• [EN] PROCESS FOR THE PREPARATION OF 2-(ARYLOXYMETHYL)-2,5,7,8-TETRAMETHYLCHROMAN-6-OLS<br/>[FR] PROCEDE DE PREPARATION DE 2-(ARYLOXYMETHYL)-2,5,7,8-TETRAMETHYLCHROMAN-6-OLS
  申请人：SANKYO CO

  公开号：WO2000010994A1

  公开（公告）日：2000-03-02

  2-(Aryloxymethyl)-2,5,7,8-tetramethylchroman-6-ols of formula (I) , in which R?1, R2, R3, R4 and R5¿ independently of one another are each hydrogen, C¿1-4?-alkyl, C1-4-alkoxy, 1-di(C1-4-alkoxy)-C1-4-alkyl, 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 2-(C1-3-alkyl)-1,3-dioxolan-2-yl, 2-(C1-3-alkyl)-1,3-dioxan-2-yl, halogen or amino, or are a C1-4-alkyl group substituted by an aromatic or nonaromatic isocyclic or heterocyclic ring system, are prepared from 2-methyl-2-phenethyloxiranes and the correspondingly substituted phenols in three stages. The title compounds are pharmaceutical active ingredients or intermediates for the preparation of such active ingredients.
• [EN] PROCESS FOR THE PREPARATION OF 2-(AMINOPHENOXYMETHYL) CHROMANS<br/>[FR] PROCEDE SERVANT A PREPARER DES 2-(AMINOPHENOXYMETHYL) CHROMANES
  申请人：SANKYO CO

  公开号：WO2000008009A1

  公开（公告）日：2000-02-17

  2-(Aminophenoxymethyl)chromans of general formula (I) in which one of the radicals R1 to R5 is an amino group and the others are independently of one another hydrogen or C¿1-4?-alkyl, R?6¿ is hydrogen or methyl, and R?7 to R10¿ independently of one another are hydrogen, C¿1-4?-alkyl, hydroxyl, C1-4-alkoxy or C1-4-acyloxy, are prepared in one stage by catalytic hydrogenation of the corresponding 2-(nitrophenoxymethyl)chroman-4-ones above 100 °C on a platinum catalyst. The compounds which can be prepared according to the invention are intermediates in the synthesis of pharmaceutical active ingredients, in particular hypolipidemics.