1-amino-5-naphthol | 54263-77-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-amino-5-naphthol
• 英文别名: 5-(Dimethylamino)naphthalen-1-ol
• CAS: 54263-77-3
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: VCQYBGKTUNHQPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-amino-5-naphthol 、 (E)-tert-butyl 2-oxo-3-(2,2,2-trifluoroethylidene)indoline-1-carboxylate 在 C₃₃H₃₆N₄O₅ 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以95%的产率得到tert-butyl (2-((3R,4S)-7-(dimethylamino)-2-oxo-4-(trifluoromethyl)-3,4-dihydro-2H-benzo[h]chromen-3-yl)phenyl)carbamate
  参考文献：
  名称：

  萘酚与3-3-三氟亚乙基氧化吲哚的有机催化弗里德尔-克拉夫特烷基化/内酯化反应：二氢香豆素的不对称合成

  摘要：

  发现萘酚和3-三氟乙叉基吲哚会发生不对称的Friedel-Crafts烷基化/内酯化反应，仅需2.5摩尔％奎宁衍生的方酰胺催化剂即可催化，从而以高收率提供相应的α-芳基-β-三氟甲基二氢香豆素衍生物（高达99％）具有优异的对映异构和非对映异构选择性（高达98％ee，> 20：1 dr）。重要的是，在温和的反应条件下，内酯化是通过在羟吲哚的酰胺基序处萘酚羟基的亲核攻击而进行的。该方案代表了通过有效的分子内酰胺CN键断裂和酯化过程形成二氢香豆素的新策略。

  DOI：

  10.1002/anie.201609390

文献信息

• Gram-positive carbapenem antibacterials and processes for their preparation
  申请人：Choi Woo-Baeg

  公开号：US20060074070A1

  公开（公告）日：2006-04-06

  The present invention provides β-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment. The present invention is also in the field of synthetic organic chemistry and is specifically provides an improved method of synthesis of β-methyl carbapenems which are useful as antibacterial agents.

  本发明提供了β-甲基碳青霉烯化合物和制药组合物，可用于治疗细菌感染，并提供了使用这些化合物和/或组合物治疗此类感染的方法。本发明包括向需要此类治疗的宿主施用β-碳青霉烯化合物或盐和/或前药的有效量。本发明还属于合成有机化学领域，特别提供了一种改进的β-甲基碳青霉烯合成方法，其可用作抗菌剂。
• GRAM-POSITIVE CARBAPENEM ANTIBACTERIALS AND PROCESSES FOR THEIR PREPARATION
  申请人：Choi Woo-Baeg

  公开号：US20100075945A1

  公开（公告）日：2010-03-25

  The present invention provides β-methyl carbapenem compounds and pharmaceutical compositions useful in the treatment of bacterial infections and methods for treating such infections using such compounds and/or compositions. The invention includes administering an effective amount of a carbapenem compound or salt and/or prodrug thereof to a host in need of such a treatment. The present invention is also in the field of synthetic organic chemistry and is specifically provides an improved method of synthesis of β-methyl carbapenems which are useful as antibacterial agents.

  本发明提供了β-甲基碳青霉烯化合物和制药组合物，可用于治疗细菌感染，并提供使用这些化合物和/或组合物治疗此类感染的方法。本发明包括向需要此类治疗的宿主投与有效量的碳青霉烯化合物或盐和/或前药。本发明还属于合成有机化学领域，特别提供了一种改进的β-甲基碳青霉烯化合物合成方法，该方法可用作抗菌剂。
• Fast internal conversion in 1-(dimethylamino)naphthalene: Effects of methoxy substitution on the naphthalene ring
  作者：Kazuyuki Takehira、Kengo Suzuki、Hiroshi Hiratsuka、Seiji Tobita

  DOI：10.1016/j.cplett.2005.07.038

  日期：2005.9

  Radiationless transitions of 1-(dimethylamino)naphthalene (1DMAN) and its 4-, 5-, 6-, and 7-methoxy derivatives having a twisted dimethylamino group in the Franck-Condon excited state are investigated by means of picosecond time-resolved fluorescence measurements. The fast internal conversion (IC) that has previously been observed for IDMAN, is also found for its 5- and 6-methoxy derivatives, while the IC rate decreases substantially in the 4- and 7-methoxy derivatives, showing that the fast IC is related to the proximity of the S-1 and S-2 states and also to the electronic structures of the S-1 and S-2 states. (c) 2005 Elsevier B.V. All rights reserved.
• EP1765821A4
  申请人：——

  公开号：EP1765821A4

  公开（公告）日：2009-05-20
• US6558956B1
  申请人：——

  公开号：US6558956B1

  公开（公告）日：2003-05-06