2-hydroxy-7-methoxy-1-nitrosonaphthalene | 65300-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-7-methoxy-1-nitrosonaphthalene
• 英文别名: 7-methoxy-1-nitroso-2-naphthol；7-methoxy-1-nitrosonaphthalen-2-ol；1-Nitroso-2-hydroxy-7-methoxynaphthalin；1-nitroso-7-methoxy-β-naphthol；1-nitroso-7-methoxy-2-naphthol；2-Naphthalenol, 7-methoxy-1-nitroso-
• CAS: 65300-88-1
• 化学式: C₁₁H₉NO₃
• mdl: MFCD00459576
• 分子量: 203.197
• InChiKey: UVNKSTJWSMMDEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxy-7-methoxy-1-nitrosonaphthalene 在 水 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 2-(6-(dimethylamino)-3-(dimethyliminio)-3H-xanthen-9-yl)-5-(((9'-methoxy-1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazin]-4-yl)methyl)carbamoyl)benzoate
  参考文献：
  名称：

  Rational design, synthesis, and characterization of highly fluorescent optical switches for high-contrast optical lock-in detection (OLID) imaging microscopy in living cells

  摘要：

  control of cellular processes. These studies require microscope imaging techniques and associated optical probes that provide high-contrast and high-resolution images of specific proteins and their complexes. Auto-fluorescence however, can severely compromise image contrast and represents a fundamental limitation for imaging proteins within living cells. We have previously shown that optical switch probes and optical lock-in detection (OLID) image microscopy improve image contrast in high background environments. Here, we present the design, synthesis, and characterization of amino-reactive and cell permeable optical switches that integrate the highly fluorescent fluorophore, tetramethylrhodamine (TMR) and spironaphthoxazine (NISO), a highly efficient optical switch. The NISO moiety in TMR-NISO undergoes rapid and reversible, excited-state driven transitions between a colorless Spiro (SP)-state and a colored merocyanine (MC)-state in response to irradiation with 365 and >530 nm light. In the MC-state, the TMR (donor) emission is almost completely extinguished by Forster resonance energy transfer (FRET) to the MC probe (acceptor), whereas in the colorless SP-state, the quantum yield for TMR fluorescence is maximal. Irradiation of TMR-NISO with a defined sequence of 365 and 546 nm manipulates the levels of SP and MC with concomitant modulation of FRET efficiency and the TMR fluorescence signal. High fidelity optical switching of TMR fluorescence is shown for TMR-NISO probes in vitro and for membrane permeable TMR-NISO within living cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.015
• 作为产物：
  描述：

  7-甲氧基-2-萘 在 硫酸 、 sodium hydroxide 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以89%的产率得到2-hydroxy-7-methoxy-1-nitrosonaphthalene
  参考文献：
  名称：

  亚硝基芳烃和N-杂环的无金属序列C（sp 2）-H / OH和C（sp 3）-H胺成环咪唑

  摘要：

  氢键辅助的亚硝基芳烃的邻位选择性C（sp 2）-H氨基化和随后的α-C（sp 3）-H脂肪族胺的官能化在无金属条件下实现。亚硝基芳烃和2-羟基-C-亚硝基化合物与N-杂环的环化分别提供了相对于广泛的生物学相关的环稠合的苯并咪唑和结构上新颖的多环咪唑的简便过量。发现在卤代亚硝基芳烃的C（sp 2）–H胺化过程中，亲核芳香族氢取代（S N ArH）比经典S N Ar反应更可取。

  DOI：

  10.1021/acs.orglett.7b00832

文献信息

• 1,3-Dihydro-3-(2-hydroxy-, 2-bromo- or 2-chloroethyl)-2H-isoindol-1-one
  申请人：American Home Products Corporation

  公开号：US04244966A1

  公开（公告）日：1981-01-13

  Derivatives of 1,3-dihydro-3-(2-hydroxyethyl) -2H-isoindol-1-one are disclosed. The derivatives are useful for treating ulcers in a mammal and for preventing or decreasing the secretion or availability of excessive amounts of gastric or hydrochloric acid in a mammal suffering from hyperchlorhydria and/or associated conditions.

  1,3-二氢-3-(2-羟乙基)-2H-异吲哚酮的衍生物已被披露。这些衍生物对于治疗哺乳动物的溃疡以及预防或减少患有高胃酸或/和相关症状的哺乳动物体内分泌或可用的过量胃酸或盐酸的作用是有用的。
• DXP Synthase-Catalyzed CN Bond Formation: Nitroso Substrate Specificity Studies Guide Selective Inhibitor Design
  作者：Francine Morris、Ryan Vierling、Lauren Boucher、Jürgen Bosch、Caren L. Freel Meyers

  DOI：10.1002/cbic.201300187

  日期：2013.7.22

  Put a ring on it: Selective inhibition of DXP synthase is a challenge in developing anti‐infectives targeting isoprenoid biosynthesis. DXP synthase preferentially turns over sterically demanding aryl nitroso substrates to form CN bonds, thus suggesting a new design for unnatural bisubstrate analogues as selective inhibitors of isoprenoid biosynthesis.

  戴上戒指：选择性抑制 DXP 合酶是开发针对类异戊二烯生物合成的抗感染药物的挑战。DXP 合酶优先翻转空间要求高的芳基亚硝基底物以形成 C  N 键，因此提出了一种新设计，将非天然双底物类似物用作类异戊二烯生物合成的选择性抑制剂。
• Process for preparing substituted
  申请人：Hoechst Aktiengesellschaft

  公开号：US05082932A1

  公开（公告）日：1992-01-21

  The invention relates to a process for preparing 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters of the general formula I ##STR1## which are substituted in at least one of the positions 5, 6, 7 or 8 by R=halogen, alkoxy groups or alkoxycarbonyl groups and in which X denotes an aryl group. The process comprises steps in which a) suitably substituted .beta.-naphthol is nitrosated, b) sulfonation with alkali hydrogensulfite and acid in position 4 and reduction are carried out, c) the naphthalenesulfonic acid derivative is oxidized, d) the 1,2-naphthoquinone-4-sulfonic acid formed is reacted with toluenesulfonohydrazide in an organic solvent at temperatures from 20.degree. to 100.degree. C., e) the naphthoquinonediazide compound is converted with chlorosulfonic acid or chlorosulfonic acid/thionyl chloride into the sulfonyl chloride, and f) the sulfonyl chloride is condensed with a phenolic component, a purification of the respective intermediate product by reprecipitation or recrystallization being unnecessary. The process makes a simple technical procedure possible with good yield. The compounds prepared, in particular the 1,2-naphthoquinone-(2)-diazide-4-sulfonic acid esters substituted by 6-alkoxycarbonyl groups or by 7-alkoxy groups, are used as radiation-sensitive components in radiation-sensitive mixtures.

  该发明涉及一种制备一般式I的1,2-萘醌-(2)-二氮化-4-磺酸酯的过程，其中至少在5、6、7或8位置之一被取代为R=卤素、烷氧基团或烷氧羰基团，并且其中X代表芳基团。该过程包括以下步骤：a) 适当取代的β-萘酚被硝化，b) 用碱性亚硫酸氢和酸对位于4位的磺化和还原进行处理，c) 萘磺酸衍生物被氧化，d) 形成的1,2-萘醌-4-磺酸与甲苯磺酰肼在有机溶剂中在20°C至100°C的温度下反应，e) 萘醌二氮化合物被氯磺酸或氯磺酸/亚硫酰氯转化为磺酰氯，f) 磺酰氯与酚性组分缩合，无需通过重新沉淀或再结晶净化各个中间产物。该过程采用简单的技术程序，产率高。所制备的化合物，特别是由6-烷氧羰基团或7-烷氧基取代的1,2-萘醌-(2)-二氮化-4-磺酸酯，用作辐射敏感混合物中的辐射敏感组分。
• Highly efficient green synthesis of the photochromic spironaphthoxazines using an eco-friendly choline hydroxide catalyst
  作者：Shailesh N. Vajekar、Ganapati S. Shankarling

  DOI：10.1080/00397911.2019.1694690

  日期：2020.2.1

  Abstract A greener route for the synthesis of the photochromic spironaphthoxazines employing a highly efficient, biodegradable and recyclable choline hydroxide catalyst in an aqueous medium has been described. This methodology offers diverse advantages such as mild reaction conditions, short reaction time (1 h), excellent yields (up to 91%), and operational simplicity that make it a useful and attractive

  摘要描述了一种在水性介质中使用高效、可生物降解和可回收的氢氧化胆碱催化剂合成光致变色螺萘恶嗪的绿色途径。该方法具有多种优势，例如反应条件温和、反应时间短（1 小时）、优异的产率（高达 91%）和操作简单，使其成为合成螺萘恶嗪的有用且有吸引力的选择。氢氧化胆碱显示出优异的催化性能，直至五次循环均未显着降低活性。通过1H NMR谱和熔点推断合成的螺萘恶嗪的结构。图形概要
• Spiropiperidinenaphthoxazine compound
  申请人：Showa Denko Kabushiki Kaisha

  公开号：US04772700A1

  公开（公告）日：1988-09-20

  A spiropiperidine-naphthoxazine compound represented by the following general formula (I) is valuable as a photochromic compound: ##STR1## wherein (a) R.sub.1 represents a C1-C18 alkyl group, C7-C15 aralkyl group which may be substituted, a C1-C10 alkenyl group or a C6-C15 aryl group which may be substituted, (b) R.sub.2 through R.sub.9 represent a group R.sub.1 defined above, a hydrogen atom, or a C5-C10 alicyclic ring or a norbonyl or adamantyl group, which is bonded between groups present on one skeleton carbon atom or between groups on adjacent skeleton carbon atoms (at the ortho-position), (c) R.sub. 10 represents a C1-C18 alkyl group, a C7-C15 aralkyl group which may be substituted or a C1-C10 alkenyl group, and (d) R.sub.11 through R.sub.16 represent a hydrogen atom, a C1-C9 alkyl group, a C1-C5 alkoxyl group, a halogen atom, a nitro group or a cyano group.

  一种由以下一般式（I）表示的螺环哌啶-萘氧噁啉化合物作为光变化化合物具有很大价值：##STR1## 其中（a）R.sub.1代表C1-C18烷基，C7-C15芳基烷基，可能被取代，C1-C10烯基或C6-C15芳基，可能被取代，（b）R.sub.2到R.sub.9代表上述定义的R.sub.1基团，氢原子，或者一个C5-C10脂环或一个环庚烷基或金刚烷基基团，其在一个骨架碳原子上或在相邻骨架碳原子之间（在邻位）连接，（c）R.sub.10代表C1-C18烷基，C7-C15芳基烷基，可能被取代，或C1-C10烯基，以及（d）R.sub.11到R.sub.16代表氢原子，C1-C9烷基，C1-C5烷氧基，卤素原子，硝基基团或氰基团。