5-chloro-1,3,3-trimethyl-6'-morpholinospiro(indoline-2,3'-naphtho[2,1-b][1,4]oxazine)

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 5-chloro-1,3,3-trimethyl-6'-morpholinospiro(indoline-2,3'-naphtho[2,1-b][1,4]oxazine)
• 英文别名: 5-chloro-1,3,3-trimethyl-6'-morpholinospiro(indolino-2,3'-[3H]naphth[2,1-b]oxazine)；5'-Chloro-1',3',3'-trimethyl-6-morpholin-4-ylspiro[benzo[f][1,4]benzoxazine-3,2'-indole]
• 化学式: C₂₆H₂₆ClN₃O₂
• 分子量: 447.964
• InChiKey: BKADLOBANDLHCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  37.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-chloro-1,2,3,3-tetramethyl-3H-indol-1-ium iodide 在 sodium hydroxide 作用下， 以 三氯乙烯 为溶剂， 反应 3.5h， 生成 5-chloro-1,3,3-trimethyl-6'-morpholinospiro(indoline-2,3'-naphtho[2,1-b][1,4]oxazine)
  参考文献：
  名称：

  Synthesis, characterization and photochromic studies in film of heterocycle-containing spirooxazines

  摘要：

  A series of novel heterocycle-containing spirooxazines have been designed and synthesized, and their photochromic properties were investigated under flash photolysis and continuous irradiation in particular regard to the fatigue resistance, the lifetime of the colored merocyanine form in various solutions and polymers. Especially, the characteristics of two UV-sensitive spirooxazines dispersed polymethylmethacrylate thin-films were extensively studied. Detailed studies showed that general significant shifts in the lambda(max) of the absorption spectra of the open forms, interesting fatigue resistances and emission fluorescene properties were observed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.057

文献信息

• One-Pot Synthesis of 6′-Amino-Substituted Spirooxazines
  作者：O. A. Fedorova、A. V. Koshkin、V. Lokshin、A. Samat、S. P. Gromov

  DOI：10.1055/s-2005-870006

  日期：——

  A one-pot synthesis of 6'-amino-substituted spiroindolinonaphth[2,1-b][1,4]oxazines is developed through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives and 1-amino-2-naphthol in the presence of different secondary amines and oxidizing agents using methanol or toluene as the solvent. The main advantage of the method is its simplicity, and starting from readily accessible reagents

  通过 2-methylene-1,3,3-trimethylindoline 衍生物与 1-amino-2 的缩合，一锅法合成 6'-氨基取代的螺吲哚啉萘 [2,1-b][1,4] 恶嗪-萘酚在不同的仲胺和氧化剂的存在下使用甲醇或甲苯作为溶剂。该方法的主要优点是简单，并且从容易获得的试剂开始，它可以在温和的反应条件下以良好的收率制备螺萘恶嗪的氨基衍生物。
• One-Pot Synthesis of Photochromic 6′-Amino-Substituted Spirooxazines from 1-Nitroso-2-naphthol Zinc Chelate and Indoline Base
  作者：Mei-Li Pang、Ji-Ben Meng、Hui-Juan Zhang、Pei-Pei Liu、Zhi-Hong Zou、Jie Han

  DOI：10.1055/s-0030-1258197

  日期：2010.10

  A series of spirooxazine derivatives containing nitrogen heterocycles were synthesized through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives with the zinc salt of 1-nitroso-2-naphthol using ethanol as solvent. The method is simple, starts from readily accessible and inexpensive reagents, and leads to the synthesis of 6′-substituted spirooxazines in moderate to good yields. We simplified the workup and found that, for some target compounds, recrystallization can effectively improve efficiency of the separation and purification.

  以乙醇为溶剂，通过 2-亚甲基-1,3,3-三甲基吲哚啉衍生物与 1-亚硝基-2-萘酚锌盐的缩合，合成了一系列含氮杂环的螺噁嗪衍生物。该方法简单易行，从容易获得且价格低廉的试剂开始，以中等至良好的收率合成 6′-取代的螺噁嗪。我们简化了操作步骤，并发现对于某些目标化合物，重结晶可以有效提高分离和纯化的效率。
• 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、
• Microwave-Assisted Solvent-Free Synthesis of the Substituted Spiroindolinonaphth[2,1-b][1,4]oxazines
  作者：A. V. Koshkin、O. A. Fedorova、V. Lokshin、R. Guglielmetti、J. Hamelin、F. Texier-Boullet、S. P. Gromov

  DOI：10.1081/scc-120027269

  日期：2004.1

  The synthesis of the substituted spiroindolinonaphth[2,1-b][1,4]oxazines 3a-e is developed through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives and 1-nitroso-2-naphthol under microwave irradiation. In the same conditions, in presence of morpholine the 6'-morpholinosubstituted compounds 4a, b, d, e are formed. The main advantages of the method are the short reaction time, solvent-free reaction condition, cleaner reaction products and the higher product yields in comparison with known methods of synthesis.
• US4913544A
  申请人：——

  公开号：US4913544A

  公开（公告）日：1990-04-03