2-hydroxy-3-piperidinocarbonylnaphthalene | 3692-69-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-hydroxy-3-piperidinocarbonylnaphthalene
• 英文别名: 3-hydroxy-2-naphthoic acid-N-piperidinylamide；1-(3-hydroxy-naphthalene-2-carbonyl)-piperidine；1-(3-hydroxy-[2]naphthoyl)-piperidine；1-(3-Hydroxy-[2]naphthoyl)-piperidin；(3-Hydroxynaphthalen-2-yl)(piperidin-1-yl)methanone；(3-hydroxynaphthalen-2-yl)-piperidin-1-ylmethanone
• CAS: 3692-69-1
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: SWULXLRLSMCRQM-UHFFFAOYSA-N

物化性质

• 沸点：
  467.3±28.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-hydroxy-3-piperidinocarbonylnaphthalene 在 lithium aluminium tetrahydride 、 溶剂黄146 、 三乙胺 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 生成 5'-piperidinomethyl-1,3,3-trimethylspiro(indoline-2,3'-<3H>naphtho<2,1-b><1,4>oxazine)
  参考文献：
  名称：

  Cation Complexation, Photochromism, and Reversible Ion-Conducting Control of Crowned Spironaphthoxazine

  摘要：

  A spironaphthoxazine derivative incorporating a monaza-12-crown-4 moiety at the 5'-position has been designed as a light-resistant, cation-complexable photochromic compound. Complexation of alkali metal ions by the crown moiety in the crowned spironaphthoxazine allows the spironaphthoxazine skeleton to isomerize to its corresponding open colored form, even under dark conditions. Specifically, Li+ complexation greatly stabilizes the open colored form due to the intramolecular interaction between its oxo group and crown-complexed cation, as well as the selective Li+ complexation of its 12-crown-4 moiety. Taking advantage of the high Li+ selectivity in the cation-induced isomerization of crowned spironaphthoxazine, the thermal stability of the open colored form can be modulated continuously by added Li+ concentrations. Even in the presence of the metal ion, UV- and visible-light irradiation led to further isomerization to the open form and back-isomerization to the initial closed form, respectively. Photoisomerization of crowned spironaphthoxazine to its open form promoted Li+ binding due to the additional axial interaction with the crown-complexed Li+, while that back to the closed form attenuated the cation binding. The photoinduced change in the cation-binding ability of crowned spironaphthoxazine, which possesses high light-fatigue resistance, has led to a highly reversible, photochemical switching system of ionic conduction.

  DOI：

  10.1021/jo00085a009
• 作为产物：
  描述：

  2-羟基-3-萘甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 2-hydroxy-3-piperidinocarbonylnaphthalene
  参考文献：
  名称：

  Cation Complexation, Photochromism, and Reversible Ion-Conducting Control of Crowned Spironaphthoxazine

  摘要：

  A spironaphthoxazine derivative incorporating a monaza-12-crown-4 moiety at the 5'-position has been designed as a light-resistant, cation-complexable photochromic compound. Complexation of alkali metal ions by the crown moiety in the crowned spironaphthoxazine allows the spironaphthoxazine skeleton to isomerize to its corresponding open colored form, even under dark conditions. Specifically, Li+ complexation greatly stabilizes the open colored form due to the intramolecular interaction between its oxo group and crown-complexed cation, as well as the selective Li+ complexation of its 12-crown-4 moiety. Taking advantage of the high Li+ selectivity in the cation-induced isomerization of crowned spironaphthoxazine, the thermal stability of the open colored form can be modulated continuously by added Li+ concentrations. Even in the presence of the metal ion, UV- and visible-light irradiation led to further isomerization to the open form and back-isomerization to the initial closed form, respectively. Photoisomerization of crowned spironaphthoxazine to its open form promoted Li+ binding due to the additional axial interaction with the crown-complexed Li+, while that back to the closed form attenuated the cation binding. The photoinduced change in the cation-binding ability of crowned spironaphthoxazine, which possesses high light-fatigue resistance, has led to a highly reversible, photochemical switching system of ionic conduction.

  DOI：

  10.1021/jo00085a009

文献信息

• 3,3-bis(aryl)-5-((N-(un)substituted)amido)naphthopyrans, their preparation, compositions and (co)polymer matrices containing them
  申请人：Corning S.A.

  公开号：EP1038870A1

  公开（公告）日：2000-09-27

  The object of the present invention is novel naphthopyran compounds as well as the compositions and (co)polymer matrices containing them. Said compounds have interesting photochromic properties. Another object of the present invention is a method of preparing said novel compounds.

  本发明的对象是新颖的萘吡喃化合物，以及含有它们的组合物和（共）聚合物基体。所述化合物具有有趣的光致变色性质。本发明的另一个对象是制备所述新颖化合物的方法。
• Enantioselective Oxidative Biaryl Coupling Reactions Catalyzed by 1,5-Diazadecalin Metal Complexes:  Efficient Formation of Chiral Functionalized BINOL Derivatives
  作者：Xiaolin Li、J. Brian Hewgley、Carol A. Mulrooney、Jaemoon Yang、Marisa C. Kozlowski

  DOI：10.1021/jo0340206

  日期：2003.7.1

  ligands in the enantioselective oxidative biaryl coupling of substituted 2-naphthol derivatives. Under the optimal conditions employing 2.5-10 mol % of a 1,5-diaza-cis-decalin copper(II) catalyst with oxygen as the oxidant, enantioselective couplings (44-96% ee) could be achieved for a range of 3-substituted 2-naphthols including the ester, ketone, phosphonyl, and sulfonyl derivatives. The relationship

  已经研究了手性的1，5-二氮杂-顺式十氢化萘作为取代的2-萘酚衍生物的对映选择性氧化性联芳基偶联中的配体。在最佳条件下，使用2.5-10 mol％的1,5-二氮杂-顺-十氢化萘铜（II）催化剂，用氧气作为氧化剂，在3-范围内可以实现对映选择性偶联（44-96％ee）取代的2-萘基，包括酯，酮，膦酰基和磺酰基衍生物。萘原料的取代与反应性/选择性之间的关系由几个共同作用的因素决定：（1）取代基对底物氧化电位的影响；
• A concept for stimulated proton transfer in 1-(phenyldiazenyl)naphthalen-2-ols
  作者：S. Hristova、V. Deneva、M. Pittelkow、A. Crochet、F.S. Kamounah、K.M. Fromm、P.E. Hansen、L. Antonov

  DOI：10.1016/j.dyepig.2018.03.070

  日期：2018.9

  shown that Sudan I (1) exists as a tautomeric mixture. The effect of the solvents is minimized by the existing intramolecular hydrogen bond. Therefore, the influence on the tautomeric state in structurally modified 1 has been investigated. Structure 2 contains an additional OH-group, which deprotonates easily and affects the position of the tautomeric equilibrium by changing the electronic properties

  一系列萘酚（的芳基偶氮衍生物的1 - 3）通过的UV-Vis和在不同溶剂中，以及通过量子化学计算和X射线分析NMR光谱方法研究。先前的研究表明，苏丹I（1）以互变异构混合物的形式存在。通过现有的分子内氢键使溶剂的影响最小化。因此，已经研究了对结构修饰的1中互变异构状态的影响。结构2包含另外的OH-基团，其易于去质子化并通过改变取代基的电子性质影响互变异构平衡的位置。在3中实施侧臂为来自偶氮基团的氮和来自哌啶单元的氮之间的互变异构质的竞争创造了条件。在这种情况下，实现了使用酸作为刺激来控制互变异构过程。
• 1-N-alkyl-5'-[(N'-(un)substituted)amido]spiroindolinonaphthoxazines, their preparation, compositions and (co)polymer matrices containing them
  申请人：Corning S.A.

  公开号：EP1044978A3

  公开（公告）日：2001-05-09

  The object of the present invention is novel spiroindolinonaphthoxazine compounds as well as the compositions and (co)polymer matrices containing them. Said compounds have interesting photochromic properties. Another object of the present invention is a method of preparing said novel compounds.

  本发明的目的是新型的螺合吲哚萘氧嗪化合物，以及含有它们的组合物和（共）聚合物基质。所述化合物具有有趣的光致变色性能。本发明的另一个目的是一种制备上述新型化合物的方法。
• [EN] COMPOUNDS USEFUL IN THE TREATMENT OF INFLAMMATORY DISEASES<br/>[FR] COMPOSES UTILISES DANS LE TRAITEMENT DE MALADIES INFLAMMATOIRES
  申请人：GLAXO GROUP LTD

  公开号：WO2000037444A1

  公开（公告）日：2000-06-29

  There are provided according to the invention, novel compounds of formula (I) wherein R?1, R2, R3, R4, R5 and R6¿ are as defined in the specification, processes for preparing them, formulations containing them and their use in therapy for the treatment of inflammatory diseases.

  根据本发明提供了一种新的化合物式(I)，其中R?1、R2、R3、R4、R5和R6¿如规范中所定义，制备它们的过程，含有它们的配方以及它们在治疗炎症性疾病方面的用途。