1-amino-5,6,7,8-tetrahydronaphthalen-2-ol | 28093-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-amino-5,6,7,8-tetrahydronaphthalen-2-ol
• 英文别名: 5-Amino-6-oxy-1.2.3.4-tetrahydro-naphthalin；5-Amino-6-oxy-tetralin；1-Amino-5,6,7,8-tetrahydro-[2]naphthol；5-Amino-tetralol-(6)
• CAS: 28093-96-1
• 化学式: C₁₀H₁₃NO
• 分子量: 163.219
• InChiKey: UTTGMGFDKHEFJY-UHFFFAOYSA-N

物化性质

• 沸点：
  324.3±42.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

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：

  1-amino-5,6,7,8-tetrahydronaphthalen-2-ol 在 氯化亚砜 、 对甲苯磺酸 、 2,3-二甲基苯胺 作用下， 以 various solvent(s) 为溶剂， 反应 7.0h， 生成 6,6',7,7',8,8',9,9'-Octahydro-2,2'-(1,4-naphthylen)dinaphth<1,2-d>oxazol
  参考文献：
  名称：

  Frischkorn, Hans; Pintschovius, Ulrich; Schinzel, Erich, Liebigs Annalen der Chemie, 1982, # 8, p. 1423 - 1433

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methoxy-5,6,7,8-tetrahydro-[1]naphthylamine 在 盐酸 作用下， 生成 1-amino-5,6,7,8-tetrahydronaphthalen-2-ol
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• Transition‐Metal‐Free C(sp ² )–C(sp ² ) Cross‐Coupling of Diazo Quinones with Catechol Boronic Esters
  作者：Kai Wu、Liang‐Liang Wu、Cong‐Ying Zhou、Chi‐Ming Che

  DOI：10.1002/anie.202006542

  日期：2020.9.7

  developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi‐substituted triphenylenes and three bioactive natural products

  无过渡金属的C（sp 2）-C（sp 2）开发了重氮醌与邻苯二酚硼酸酯的交叉偶联反应。通过该方案，可以在温和条件下以高收率或高收率获得各种联芳基和烯基苯酚。该反应具有多种功能，可用于药物和天然产物的衍生化。该方法的合成效用通过短取代多取代的三亚苯基和三种生物活性天然产物厚朴酚，苦味素M和呋喃呋喃A的合成得到证明。机理研究和密度泛函理论（DFT）计算表明，该反应涉及到硼酸酯由单重醌卡宾构成，然后通过逐步机理进行1,2-重排。
• Antitumor Agents. 5. Synthesis, Structure−Activity Relationships, and Biological Evaluation of Dimethyl-5<i>H</i>-pyridophenoxazin-5-ones, Tetrahydro-5<i>H</i>-benzopyridophenoxazin-5-ones, and 5<i>H</i>-Benzopyridophenoxazin-5-ones with Potent Antiproliferative Activity
  作者：Adele Bolognese、Gaetano Correale、Michele Manfra、Antonio Lavecchia、Ettore Novellino、Stefano Pepe

  DOI：10.1021/jm050745l

  日期：2006.8.1

  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.
• FRISCHKORN, H.;PINTSCHOVIUS, U.;SCHINZEL, E., LIEBIGS ANN. CHEM., 1982, N 8, 1423-1433
  作者：FRISCHKORN, H.、PINTSCHOVIUS, U.、SCHINZEL, E.

  DOI：——

  日期：——
• US4119634A
  申请人：——

  公开号：US4119634A

  公开（公告）日：1978-10-10
• US4110246A
  申请人：——

  公开号：US4110246A

  公开（公告）日：1978-08-29