6-methoxy-2-naphthamide | 111359-68-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methoxy-2-naphthamide
• 英文别名: 6-Methoxynaphthalene-2-carboxamide
• CAS: 111359-68-3
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD18905866
• 分子量: 201.225
• InChiKey: BGWQUNHORXXTHE-UHFFFAOYSA-N

物化性质

• 熔点：
  200-203 °C(Solv: water (7732-18-5))
• 沸点：
  434.1±18.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  6-methoxy-2-naphthamide 在 劳森试剂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 3.0h， 生成 4-(chloromethyl)-2-(2-methoxynaphthalen-6-yl)thiazole
  参考文献：
  名称：

  Naphthalenyl derivatives for hitting P-gp/MRP1/BCRP transporters

  摘要：

  Substituted naphthalenyl derivatives bearing oxazole, or thiazole or furyl heteronuclei have been carried out as bioisosters of aryl-oxazoles and -thiazoles derivatives previously reported in order to investigate the role of the hindrance on the activity towards P-gp/BCRP/and MRP1 transporters. In addition, the role of naphthalenyl group to modulate P-gp intrinsic activity of these compounds was ascertained.The results demonstrated that all naphthalenyl derivatives displayed comparable P-gp activity with respect to lead compounds previously characterized in our SAR studies but were less active towards BCRP and MRP1 pumps. In terms of intrinsic activity, the replacement of aryl with naphthalenyl moiety led to P-gp inhibitors, unambiguous or ambiguous substrates on the base of the heteronucleus and the substituent on the naphthalenyl fragment. Indeed, oxazole derivatives were: inhibitors (R = H, F, OH), unambiguous substrates (R = OCH3), or ambiguous substrate (R = Br); thiazole derivatives were: unambiguous substrates (R = OCH3, Br), or ambiguous substrates (R = H, F). Finally furyl derivatives were ambiguous substrates. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.021
• 作为产物：
  描述：

  Amino-(6-methoxynaphthalen-2-yl)methanol 在 叔丁基过氧化氢 、 氨 、 四丁基碘化铵 作用下， 以 水 为溶剂， 反应 16.0h， 以37%的产率得到6-methoxy-2-naphthamide
  参考文献：
  名称：

  TBAI催化从苯乙酮和甲醇中氧化合成苯甲酰胺†

  摘要：

  已经开发出一种有趣且方便的方法，用于将苯乙酮和甲醇氧化转化为伯苯甲酰胺。通过使用四正丁基碘化铵（TBAI）作为催化剂和叔丁基氢过氧化物（TBHP）作为氧化剂，可以在水溶液中以中等至良好的收率分离出所需的苯甲酰胺。值得注意的是，不仅苯乙酮而且丙苯酮也可以用作底物。因此，我们认为这种新方法不仅是基于碘的方法的催化形式。

  DOI：

  10.1039/c4ob01203h

文献信息

• Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides<i>via</i>CC Bond Cleavage under Aqueous Conditions
  作者：Shashikant U. Dighe、Sanjay Batra

  DOI：10.1002/adsc.201500906

  日期：2016.2.4

  The visible light‐induced iodine‐catalyzed oxidative cleavage of the CC bond for transforming terminal alkynes into primary amides in the presence of ammonia under aqueous conditions is described. This metal‐free protocol which ensued via initial hydroamination of the acetylene bond followed by liberation of diiodomethane (CH2I2) was found to be applicable to aromatic, heteroaromatic and aliphatic

  描述了可见光诱导的碘催化的CC键的氧化裂解，该裂解用于在水性条件下在氨存在下将末端炔烃转化为伯酰胺。通过先乙炔键的加氢胺化反应，然后释放出二碘甲烷（CH 2 I 2）而产生的这种无金属方案适用于芳族，杂芳族和脂族炔烃。
• Palladium-catalyzed synthesis of primary benzamides from aryl bromides via a cyanation and hydration sequence
  作者：Muhammad Sharif、Xiao-Feng Wu

  DOI：10.1039/c5ra00490j

  日期：——

  An interesting and effective procedure for the synthesis of primary benzamides from aryl bromides via cyanation and in situ hydration sequence has been developed.

  已开发出一种从芳基溴化物经氰化和原位水合序列合成初级苯酰胺的有趣且有效的程序。
• Cyanation and Hydrolysis Cascade of Aryl Bromides with Cuprous Cyanide to Access Primary Amides
  作者：Chunnian Xia、Bo Hong、Xiaolin Chen、Jiawei Dai、Feng Gao、Ning Wang、Junfeng Wang、Xiao Xiao、Fengli Dai、Yifang Li

  DOI：10.1055/s-0042-1752717

  日期：2023.10

  A convenient and efficient approach for the cyanation and hydrolysis of aryl bromides to afford primary amides was developed, in which cuprous cyanide is used as a cyanide source and a catalyst. It has the advantages of excellent functional-group compatibility, medium to high yields, a one-pot procedure, and a non-noble-metal catalyst. The reaction could be performed on a gram scale to give N-ally

  开发了一种方便有效的方法，用于芳基溴的氰化和水解以提供伯酰胺，其中氰化亚铜用作氰化物源和催化剂。具有官能团相容性好、中高产率、一锅法、非贵金属催化剂等优点。该反应可以在克级进行，以73%的产率得到N-烯丙基-N-甲基-5-硝基间苯二甲酰胺。
• p-Aminophenols, derivatives thereof and use for manufacture of a medicament
  申请人：E.R. Squibb & Sons, Inc.

  公开号：EP0221677A2

  公开（公告）日：1987-05-13

  p-Aminophenols are provided having the structure wherein m is 0 to 5; X is CH or N; R1 and R2 maybe the same or different and are H, lower alkyl, aryl, hydroxy, hydroxyalkyleneoxy, alkylthio, alkoxy, alkanoyloxy, aryloxy, halo, carboxy, alkoxycarbonyl or amido; R3 is H, lower alkyl, alkanoyl or aroyl; and R" is H, lower alkyl or alkanoyl, and including acid-addition salts thereof, with the proviso that when X is CH, m is 0 and R1 is H, and when R4 is H, R2 is other than alkoxy, H or hydroxy, and when R4 is benzoyl, R2 is other than H. These compounds together with the compounds defined in the above proviso are useful as inhibitors of leukotriene production and as such are useful as antiallergy, anti-inflammatory and anti-psoriatic agents.

  对氨基苯酚具有以下结构 其中 m 是 0 至 5；X 是 CH 或 N；R1 和 R2 可以相同或不同，并且是 H、低级烷基、芳基、羟基、羟基烷氧基、烷硫基、烷氧基、烷酰氧基、芳氧基、卤代、羧基、烷氧羰基或氨基；R3 是 H、低级烷基、烷酰基或芳基；和 R "为 H、低级烷基或烷酰基，包括其酸加成盐，但条件是当 X 为 CH 时，m 为 0，R1 为 H，当 R4 为 H 时，R2 除烷氧基、H 或羟基外，R4 为苯甲酰基时，R2 除 H 外。这些化合物与上述但书中定义的化合物一起可用作白三烯生成抑制剂，因此可用作抗过敏、抗炎和抗银屑病药物。
• Fries; Schimmelschmidt, Chemische Berichte, 1925, vol. 58, p. 2844
  作者：Fries、Schimmelschmidt

  DOI：——

  日期：——