5-Methoxy-2-tetralon-oxim | 3899-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 5-Methoxy-2-tetralon-oxim
• 英文别名: N-(5-methoxy-3,4-dihydro-1H-naphthalen-2-ylidene)hydroxylamine
• CAS: 3899-04-5
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: VBDDTBNCOODXFS-UHFFFAOYSA-N

物化性质

• 沸点：
  378.3±42.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Methoxy-2-tetralon-oxim 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 5-甲氧基-2-四氢萘胺
  参考文献：
  名称：

  Synthesis and Antifungal Activities of Novel 2-Aminotetralin Derivatives

  摘要：

  Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoli ne ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14 alpha-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.

  DOI：

  10.1021/jm0701167
• 作为产物：
  描述：

  5-甲氧基-2-萘满酮 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以72 %的产率得到5-Methoxy-2-tetralon-oxim
  参考文献：
  名称：

  铱催化肟转移加氢合成N-烷氧基胺和羟胺

  摘要：

  发现阳离子铱（Ir）配合物催化肟的转移加氢以得到N-烷氧基胺和羟胺，并且三氟乙酸加速了反应。该协议的实际应用通过克级转化和杀菌剂 furmecyclox (BAS 389F) 的两步合成得到证明，总产量分别为 92% 和 85%。证明了使用手性 Ir 配合物提供手性N-烷氧基胺的不对称方案，但获得的低产率/ee 表明需要进一步开发。

  DOI：

  10.1039/d2ob01084d

文献信息

• TETRAHYDRONAPHTHALENE DERIVATIVE
  申请人：ONO Pharmaceutical Co., Ltd.

  公开号：EP3409658A1

  公开（公告）日：2018-12-05

  A compound shown by general formula (I-1) (in the formula, all symbols are as stated in the specification.) has selective S1P5 receptor-binding activity. Adjusting this activity make s it possible to obtain a therapeutic agent for S1P5-mediated diseases, for example, neurod egenerative diseases such as schizophrenia and Binswanger's disease.

  通式（I-1）所示的化合物（式中所有符号如说明书所述）具有选择性 S1P5 受体结合活性。通过调整这种活性，可以获得一种治疗 S1P5 介导的疾病（例如神经退行性疾病，如精神分裂症和宾斯旺格氏病）的药物。
• Tetrahydronaphthalene derivative
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：US10730830B2

  公开（公告）日：2020-08-04

  A compound of general formula (I-1): wherein the symbols are defined in the specification, has a selective S1P5 receptor binding activity and modulates the function of an S1P5 receptor, and can therefore be a therapeutic agent for a S1P5-mediated disease, for example, neurodegenerative diseases such as schizophrenia, Binswanger's disease and the like.

  通式(I-1)的化合物： 其中的符号在说明书中定义，具有选择性 S1P5 受体结合活性并调节 S1P5 受体的功能，因此可作为 S1P5 介导的疾病（例如精神分裂症、宾斯旺格病等神经退行性疾病）的治疗剂。
• EP3409658
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis and Antifungal Activities of Novel 2-Aminotetralin Derivatives
  作者：Bin Yao、Haitao Ji、Yongbin Cao、Youjun Zhou、Jü Zhu、Jiaguo Lü、Yaowu Li、Jun Chen、Canhui Zheng、Yuanying Jiang、Rongmei Liang、Hui Tang

  DOI：10.1021/jm0701167

  日期：2007.11.1

  Novel 2-aminotetralin derivatives were synthesized as antifungal agents. The 2-aminotetralin scaffold was chemically designed to mimic the tetrahydroisoquinoli ne ring of the lead molecule described before. Their antifungal activities were evaluated in vitro by measuring the minimal inhibitory concentrations (MICs). Compounds 10a, 12a, 12c, 13b, and 13d are more potent than fluconazole against seven testing human fungal pathogens. Compound 10b exhibits much higher antifungal activities against all of the four fluconazole-resistant clinic Candida albicans strains than the control drugs including amphotericin B, terbinafine, ketoconazole, and itraconazole. The mode of action of some compounds to the potential receptor lanosterol 14 alpha-demethylase (CYP51) was investigated by molecular docking. The studies presented here provide a new structural type for the development of novel antifungal compounds. Furthermore, 10b was evaluated in vivo by a rat vaginal candidiasis model, and it was found that 10b significantly decreases the number of fungal colony counts.
• Synthesis of <i>N</i>-alkoxy amines and hydroxylamines <i>via</i> the iridium-catalyzed transfer hydrogenation of oximes
  作者：Yanping Xia、Sen Wang、Rui Miao、Jianhua Liao、Lu Ouyang、Renshi Luo

  DOI：10.1039/d2ob01084d

  日期：——

  hydrogenation of oximes to access N-alkoxy amines and hydroxylamines, and the reaction was accelerated by trifluoroacetic acid. The practical application of this protocol was demonstrated by a gram-scale transformation and two-step synthesis of the fungicide furmecyclox (BAS 389F) in overall yields of 92 and 85%, respectively. An asymmetric protocol using chiral Ir complexes to afford chiral N-alkoxy amines was

  发现阳离子铱（Ir）配合物催化肟的转移加氢以得到N-烷氧基胺和羟胺，并且三氟乙酸加速了反应。该协议的实际应用通过克级转化和杀菌剂 furmecyclox (BAS 389F) 的两步合成得到证明，总产量分别为 92% 和 85%。证明了使用手性 Ir 配合物提供手性N-烷氧基胺的不对称方案，但获得的低产率/ee 表明需要进一步开发。