4-Piperidino-1,2-naphthoquinone | 25107-82-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-Piperidino-1,2-naphthoquinone
• 英文别名: 4-Piperidin-1-ylnaphthalene-1,2-dione
• CAS: 25107-82-8
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: CJXORYYEEAJZSR-UHFFFAOYSA-N

物化性质

• 熔点：
  140-150 °C
• 沸点：
  403.0±45.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Piperidino-1,2-naphthoquinone 在 盐酸羟胺 作用下， 以 乙醇 为溶剂， 以8%的产率得到1-亚硝基-4-(哌啶-1-基)萘-2-醇
  参考文献：
  名称：

  Red Colouring Photochromic 6′-Substituted Spiroindolinon Aphth[2,1-b][1,4]Oxazines

  摘要：

  Electron donating/withdrawing substituents and electronegative centres have been successfully employed in substantially widening the range of photo-generated colours available in the spiroindolinonaphthoxazine class of photochromic materials.

  DOI：

  10.1080/10587259408037780
• 作为产物：
  描述：

  哌啶 、 4-diethylamino-1,2-naphthoquinone 在 calcium chloride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到4-Piperidino-1,2-naphthoquinone
  参考文献：
  名称：

  Tsizin, Yu. S.; Chernyak, S. A.; Kornienko, N. I., Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 2381 - 2388

  摘要：

  DOI：

文献信息

• Reaction of 1,2-naphthoquinone-4-sulfonate with aliphatic amines: Structure of the colored products and kinetics.
  作者：YUTAKA ASAHI、MASAMI TANAKA、KAZUO SHINOZAKI

  DOI：10.1248/cpb.32.3093

  日期：——

  Substitution of the 4-sulfonate in sodium 1, 2-naphthoquinone-4-sulfonate (I) with many kinds of aliphatic amines (II) yields colored 4-substituted 1, 2-naphthoquinones (Q) : 4-morpholino-Q (IIIa), 4-piperidino-Q (IIIb), 4-pyrrolidino-Q (IIIc), 4-(1, 2, 4-triazol-1-yl)-Q (IIId), 4-(2-pyrrolyl)-Q (IIIe), 4-dimethylamino-Q (IIIf), 4-diethylamino-Q (IIIg), 4-isopropylamino-Q (IIIh), and 4-(4-amino-2-methyl-5-pyrimidylmethylamino)-Q (IIIi). The eliminated sulfite adds rapidly to the 4-position in I to form a colorless by-product, disodium 2-hydroxy-1-oxo-1, 4-dihydro-4, 4-naphthalenedisulfonate (IV). The rates of reactions were measured by polarography. The formations of IIIa and IV are successive second-order reactions. The pH profile of the rate constant, with a rounded peak at pH 10, suggests nucleophilic substitution of the free base (II) at the 4-carbon in the o-quinone form (I). The hydrolysis of IIIa to 2-hydroxy-1, 4-naphthoquinone (V) is an acid-base-catalyzed pseudo-first-order reaction. The best conditions for photometric determination of morpholine (IIa) were found to be reaction of IIa with excess I at pH 8 and 25°C for 30 min.

  将钠1,2-萘醌-4-磺酸盐(I)中的4-磺酸基替换成多种脂肪胺(II)，得到有色的4-取代的1,2-萘醌(Q)：4-吗啉代-Q(IIIa)、4-哌啶代-Q(IIIb)、4-吡咯烷代-Q(IIIc)、4-(1,2,4-三唑-1-基)-Q(IIId)、4-(2-吡咯基)-Q(IIIe)、4-二甲氨基-Q(IIIf)、4-二乙氨基-Q(IIIg)、4-异丙氨基-Q(IIIh)及4-(4-氨基-2-甲基-5-嘧啶基甲氨基)-Q(IIIi)。被取代的亚硫酸盐迅速加到I的4位上，形成一种无色的副产物，即二钠2-羟基-1-氧-1,4-二氢-4,4-萘二磺酸盐(IV)。反应速率是通过极谱法测量的。IIIa和IV的生成是连续的二级反应。速率常数的pH曲线在pH10处有一个圆顶峰，这说明自由基(II)在邻醌形式(I)的4-碳位上发生了亲核取代反应。IIIa水解成2-羟基-1,4-萘醌(V)是一个酸碱催化的假一级反应。通过研究找到了用光度法测定吗啉(IIa)的最优条件，即IIa与过量的I在pH8和25摄氏度下反应30分钟。
• A concentration dependent auto-relay-recognition by the same analyte: a dual fluorescence switch-on by hydrogen sulfide via Michael addition followed by reduction and staining for bio-activity
  作者：Avijit Kumar Das、Shyamaprosad Goswami、Gorachand Dutta、Sibaprasad Maity、Tarun kanti Mandal、Kalyani Khanra、Nandan Bhattacharyya

  DOI：10.1039/c5ob02008e

  日期：——

  H₂S is shown, for the first time, to play an extraordinary dual role due to its nucleophilicity and reducing property with a single chemosensor.

  H₂S首次被证明具有非凡的双重作用，这是由于它的亲核性和还原性质与单一化学传感器共同发挥作用。
• Synthesis and properties of 1,3,3-trimethylspiro[indoline-2,3′-naphtho[2,1-b][1,4]oxazin]-6′-amine, a novel, red colouring photochromic spirooxazine
  作者：Mark York、Richard A. Evans

  DOI：10.1016/j.tetlet.2010.02.105

  日期：2010.4

  The synthesis and photochromic properties of 1,3,3-trimethylspiro[indoline-2,3′-naphtho[2,1-b][1,4]oxazin]-6′-amine, a novel red-colouring photochromic spirooxazine and derivatives is reported. The synthesis proceeds via an unusual one-pot transamination, oxime formation, N–O bond cleavage, spirooxazine formation process.

  新型红色光致变色螺恶嗪1,3,3-三甲基螺[吲哚啉-2,3'-萘并[2,1- b ] [1,4]恶嗪] -6'-胺的合成及光致变色性能有衍生产品报道。合成过程通过不寻常的一锅转氨反应，肟形成，N–O键裂解，螺恶嗪形成过程进行。
• Photochromic articles
  申请人：PILKINGTON PLC

  公开号：EP0245020A2

  公开（公告）日：1987-11-11

  A plastic organic photochromic article, typically a lens such as an ophthalmic lens or a window such as a vehicle roof light, comprising a plastics host material having a photochromic compound incorporated therein or applied thereto, the article being characterised in that it exhibits the following properties, measured at Air Mass 2 at 25 °C: (a) an integrated visible transmission in the faded state (B.IVT) ranging from 90 to 25 %, (b) an integrated visible transmission in the darkened state (D.IVT) ranging from 1 to 50 %, preferably 4 to 30 %, (c) the rate of darkening of the article when it is exposed to actinic radiation is such that 88% of the darkening range is achieved in 30 seconds or less, i.e.TB8 30 secs, (d) the rate of fading of the article from its fully darkened condition is such that more than 60 % of the optical density range is recovered in 60 seconds, i.e. % ODG-1 60%, and (e) the induced optical density of the article, i.e. the change in the optical density of the article, in moving from the faded state (B.IVT) to the darkened state (D.IVT), is greater than 0.45. Typically, the photochromic compound is a spiro-oxazine compound of general formula (II),

  一种塑料有机光致变色制品，通常是镜片（如眼科镜片）或车窗（如车顶灯），由塑料主材料组成，塑料主材料中含有或涂有光致变色化合物： (a) 在褪色状态下的综合可见光透射率（B.IVT）从 90%到 25%不等、 (b) 变暗状态下的综合可见透射率（D.IVT）为 1-50%，最好为 4-30%、 (c) 当物品暴露在光辐射下时，其变黑的速度能在 30 秒或更短时间内达到变黑范围的 88%，即 TB8 30 秒、 (d) 物品从完全变暗状态开始褪色的速度为 60 秒内恢复 60%以上的光密度范 围，即 % ODG-1 60%，以及 (e) 物品的诱导光密度，即物品从褪色状态（B.IVT）到变暗状态（D.IVT）的光密度变化大于 0.45。 典型的光致变色化合物是通式（II）的螺嗪化合物、
• PHOTOCHROMATIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN POLYMERIC MATERIALS
  申请人：Great Lakes Chemical (Europe) GmbH

  公开号：EP0994879B1

  公开（公告）日：2003-09-24