2-氨基-5,6,7,8-四氢-1-萘酚 | 861339-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 中文名称: 2-氨基-5,6,7,8-四氢-1-萘酚
• 英文名称: 2-amino-5,6,7,8-tetrahydronaphthalen-1-ol
• 英文别名: 6-Amino-5-oxy-1.2.3.4-tetrahydro-naphthalin；2-Amino-5,6,7,8-tetrahydro-[1]naphthol；6-Amino-5-oxy-tetralin；6-Amino-tetralol-(5)
• CAS: 861339-92-6
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: GQHYWPQAHVAGBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,8-喹啉二酮 、 2-氨基-5,6,7,8-四氢-1-萘酚 在 cobalt(II) acetate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以33%的产率得到13-Oxa-2,8-diazapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),2,4(9),5,7,11,15(20),21-octaen-10-one
  参考文献：
  名称：

  Antitumor Agents. 5. Synthesis, Structure−Activity Relationships, and Biological Evaluation of Dimethyl-5H-pyridophenoxazin-5-ones, Tetrahydro-5H-benzopyridophenoxazin-5-ones, and 5H-Benzopyridophenoxazin-5-ones with Potent Antiproliferative Activity

  摘要：

  New antiproliferative compounds, dimethyl-5H-pyrido[3,2-a] phenoxazin-5-ones (1-6), tetrahydro-5-Hbenzopyrido[2,3-j]phenoxazin-5-ones (7-9), and 5H-benzopyrido[3,2-a] phenoxazin-5-ones (10-12) were synthesized and evaluated against representative human neoplastic cell lines. Dimethyl derivatives 1-6 were more active against carcinoma than leukemia cell lines. The tetrahydrobenzo derivatives 7-9 were scarcely active, whereas the corresponding benzo derivatives 10-12 showed notable cytotoxicity against a majority of the tested cell lines. Molecular modeling studies indicated that the high potency of 10 and 11, the most cytotoxic compounds of the whole series, could be due to the position of the condensed benzene ring, which favors d-d stacking interactions with purine and pyrimidine bases in the DNA active site. Biological studies suggested that 10-12 have no effect on human topoisomerases I and II and that they induce arrest at the G2/M phase.

  DOI：

  10.1021/jm050745l
• 作为产物：
  描述：

  5,6,7,8-四氢-2-硝基萘-1-醇 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 2-氨基-5,6,7,8-四氢-1-萘酚
  参考文献：
  名称：

  Schroeter, Justus Liebigs Annalen der Chemie, 1922, vol. 426, p. 132

  摘要：

  DOI：

文献信息

• [EN] METHOD FOR INDUSTRIALLY PREPARING NITROGEN SUBSTITUTED AMINO-5,6,7,8-TETRAHYDRONAPHTHOL<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION INDUSTRIELLE D'AMINO-5,6,7,8-TÉTRAHYDRONAPHTOL SUBSTITUÉ PAR AZOTE
  申请人：SHAN DONG LUYE PHARM CO LTD

  公开号：WO2013000273A1

  公开（公告）日：2013-01-03

  A method for industrially preparing a nitrogen substituted 6-amino-5,6,7,8-tetrahydronaphthol is disclosed. The method comprises reacting a nitrogen substituted amino-5,6,7,8-tetrahydronaphthol compound of formula (II) with a 2-substituted ethyl sulfonate compound of formula (III) under an alkaline condition and in the presence of a sulfite.

  公开了一种工业制备氮取代6-氨基-5,6,7,8-四氢萘酚的方法。该方法包括在碱性条件下，在亚硫酸盐存在下，将式（II）的氮取代氨基-5,6,7,8-四氢萘酚化合物与式（III）的2-取代乙基磺酸酯化合物反应。
• METHOD FOR INDUSTRIALLY PREPARING NITROGEN SUBSTITUTED AMINO-5,6,7,8-TETRAHYDRONAPHTHOL
  申请人：Meng Qingguo

  公开号：US20140121380A1

  公开（公告）日：2014-05-01

  A method for industrially preparing a nitrogen substituted 6-amino-5,6,7,8-tetrahydronaphthol is disclosed. The method comprises includes reacting a nitrogen substituted amino-5,6,7,8-tetrahydronaphthol compound of formula (II) with a 2-substituted ethyl sulfonate compound of formula (III) under an alkaline condition and in the presence of a sulfite.

  公开了一种工业制备氮取代6-氨基-5,6,7,8-四氢萘酚的方法。该方法包括在碱性条件下，在亚硫酸盐存在下，通过将式（II）的氮取代氨基-5,6,7,8-四氢萘酚化合物与式（III）的2-取代乙基磺酸酯化合物反应来实现。
• Processes for the Preparation of Rotigotine and Intermediates Thereof
  申请人：Apotex Inc.

  公开号：US20170305877A1

  公开（公告）日：2017-10-26

  The present invention provides processes for the preparation of a compound of Formula 2 or a salt thereof, wherein R 1 is selected from the group consisting of H, C 1 -C 3 alkyl, and C(0)R 3 ; R 3 is selected from the group consisting of C 1 -C 6 alkyl, C 6 -C 10 aryl and C 7 -C 20 arylalkyl; the carbon atom marked with “*” is racemic, enantiomerically enriched in the (R)-configuration, or enantiomerically enriched in the (S)-configuration. Also provided are intermediate compounds of the processes.

  本发明提供了制备式2化合物或其盐的方法，其中R1选自H、C1-C3烷基和C(0)R3，R3选自C1-C6烷基、C6-C10芳基和C7-C20芳基烷基；标有“*”的碳原子是外消旋的，富集(R)-构型的对映体或富集(S)-构型的对映体。同时提供了所述方法的中间体化合物。
• Schroeter, Justus Liebigs Annalen der Chemie, 1922, vol. 426, p. 132
  作者：Schroeter

  DOI：——

  日期：——
• ENDODONTIC POST SYSTEM
  申请人：APOTEX INC.

  公开号：US20160297745A1

  公开（公告）日：2016-10-13

  The present invention provides processes for the preparation of a compound of Formula 2 or a salt thereof, wherein R 1 is selected from the group consisting of H, C 1 -C 3 alkyl, and C(0)R 3 ; R 3 is selected from the group consisting of C 1 -C 6 alkyl, C 6 -C 10 aryl and C 7 -C 20 arylalkyl; the carbon atom marked with “*” is racemic, enantiomerically enriched in the (R)-configuration, or enantiomerically enriched in the (S)-configuration. Also provided are intermediate compounds of the processes.