3,4-dihydro-3,6,8-trimethyl-2H-1,3-benzoxazine | 56073-40-6

• 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: 3,4-dihydro-3,6,8-trimethyl-2H-1,3-benzoxazine
• 英文别名: 3,6,8-trimethyl-2,4-dihydro-1,3-benzoxazine
• CAS: 56073-40-6
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: NYRGKWKZAUQPSK-UHFFFAOYSA-N

物化性质

• 沸点：
  250.5±19.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-3,6,8-trimethyl-2H-1,3-benzoxazine 在 primary amine 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以48%的产率得到6,6'-((methylenebis(methylazanediyl))bis(methylene))bis(2,4-dimethylphenol)
  参考文献：
  名称：

  Tzschoppe, D.; Vebrel, J.; Schwob, J. M., Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 1, p. 45 - 48

  摘要：

  DOI：
• 作为产物：
  描述：

  6,6'-((methylenebis(methylazanediyl))bis(methylene))bis(2,4-dimethylphenol) 在 氢气 作用下， 以 氘代氯仿 为溶剂， 以85%的产率得到3,4-dihydro-3,6,8-trimethyl-2H-1,3-benzoxazine
  参考文献：
  名称：

  Tzschoppe, D.; Vebrel, J.; Schwob, J. M., Bulletin des Societes Chimiques Belges, 1986, vol. 95, # 1, p. 45 - 48

  摘要：

  DOI：

文献信息

• Self termination of ring opening reaction of<i>p</i>-substituted phenol-based benzoxazines: An obstructive effect<i>via</i>intramolecular hydrogen bond
  作者：Suwabun Chirachanchai、Apirat Laobuthee、Suttinun Phongtamrug

  DOI：10.1002/jhet.130

  日期：2009.7

  The ring opening polymerizations of p-substituted phenol-based benzoxazines are self-terminated as soon as dimers form. The polymerization of benzoxazine monomers does not proceed according to the theoretical mechanism even though the conditions, temperature, molar ratio, solvent polarity, and reactant ratio are varied. The speculated mechanism, involving the unique structure of a dimer with inter-

  所述开环 聚合的p -取代酚系苯并恶嗪是自终止，一旦二聚体形成。该聚合的即使条件，温度，摩尔比，溶剂极性和反应物比率变化，苯并恶嗪单体也不会根据理论机理进行。推测的机理涉及具有分子间和分子内氢键的二聚体的独特结构，用于解释对开环聚合的阻碍作用。在本文中，我们阐明了化合物的立体结构控制反应并阻止理论机理所预期的聚合的重要情况。J.杂环化​​学，（2009）。
• Benzoxazine Oligomers:  Evidence for a Helical Structure from Solid-State NMR Spectroscopy and DFT-Based Dynamics and Chemical Shift Calculations
  作者：Gillian R. Goward、Daniel Sebastiani、Ingo Schnell、Hans Wolfgang Spiess、Ho-Dong Kim、Hatsuo Ishida

  DOI：10.1021/ja029059r

  日期：2003.5.1

  to elucidate the supramolecular structure of a series of benzoxazine oligomers. Intramolecular hydrogen bonds are characterized and identified as the driving forces for ring-shape and helical conformations of trimeric and tetrameric units. In fast MAS (1)H NMR spectra, the resonances of the protons forming the hydrogen bonds can be assigned and used for validating and refining the structure by means

  分子建模、DFT 计算和先进的固态 NMR 实验相结合，用于阐明一系列苯并恶嗪低聚物的超分子结构。分子内氢键被表征并确定为三聚体和四聚体单元的环状和螺旋构象的驱动力。在快速 MAS (1) H NMR 光谱中，可以分配形成氢键的质子的共振，并用于通过基于 DFT 的几何优化和 (1) H 化学位移计算来验证和改进结构。同样支持这些提议的结构是同核 (1)H[bond](1)H 双量子 NMR 光谱，它确定了每种材料中的局部质子 - 质子邻近性。此外，通过分析偶极旋转边带模式获得的定量 (15)N[键](1)H 距离测量证实了四聚体的优化几何形状。这些结果清楚地支持苯并恶嗪聚合物的预测螺旋几何形状。这种几何结构，其中 N...H...O 和 O...H...O 氢键在螺旋内部受到保护，可以解释聚苯并恶嗪材料的许多示例性化学性质。先进的实验固态 NMR 光谱与计算几何优化、总能量和 NMR 光
• USE OF TETRAHYDROBENZOXAZINES AS STABILISERS
  申请人：BASF SE

  公开号：US20140163224A1

  公开（公告）日：2014-06-12

  The use of tetrahydrobenzoxazines I where R 1 is a hydrocarbyl radical and R 2 , R 3 , R 4 and R 5 are each independently hydrogen atoms, hydroxyl groups or hydrocarbyl radicals, and where R 2 to R 5 may also form a second and a third tetrahydrooxazine ring, with the proviso that at least one of the substituents has from 4 to 3000 carbon atoms and the remaining substituents, when they are hydrocarbyl radicals, each have from 1 to 20 carbon atoms, as stabilizers for stabilizing inanimate organic material, especially turbine fuels, against the action of light, oxygen and heat.

  使用四氢苯并噁唑，其中R1为烃基基团，R2、R3、R4和R5分别独立地为氢原子、羟基或烃基基团，其中R2到R5还可以形成第二个和第三个四氢噁唑环，但至少有一个取代基含有4到3000个碳原子，其余的取代基（当它们是烃基基团时）每个都含有1到20个碳原子，作为稳定剂，以稳定无机有机材料，特别是涡轮燃料，防止光、氧和热的作用。
• 6,6′-((Methylazanedyl)bis(methylene))bis(2,4-dimethylphenol) Induces Autophagic Associated Cell Death through mTOR-Mediated Autophagy in Lung Cancer
  作者：Nicharat Sriratanasak、Worawat Wattanathana、Pithi Chanvorachote

  DOI：10.3390/molecules27196230

  日期：——

  Autophagy is the multistep mechanism for the elimination of damaged organelles and misfolded proteins. This mechanism is preceded and may induce other program cell deaths such as apoptosis. This study unraveled the potential pharmacological effect of 24MD in inducing the autophagy of lung cancer cells. Results showed that 24MD was concomitant with autophagy induction, indicating by autophagosome staining and the induction of ATG5, ATG7 and ubiquitinated protein, p62 expression after 12-h treatment. LC3-I was strongly conversed to LC3-II, and p62 was downregulated after 24-h treatment. The apoptosis-inducing activity was found after 48-h treatment as indicated by annexin V-FITC/propidium iodide staining and the activation of caspase-3. From a mechanistic perspective, 24-h treatment of 24MD at 60 μM substantially downregulated p-mTOR. Meanwhile, p-PI3K and p-Akt were also suppressed by 24MD at concentrations of 80 and 100 μM, respectively. We further confirmed m-TOR-mediated autophagic activity by comparing the effect of 24MD with rapamycin, a potent standard mTOR1 inhibitor through Western blot and immunofluorescence assays. Although 24MD could not suppress p-mTOR as much as rapamycin, the combination of rapamycin and 24MD could increase the mTOR suppressive activity and LC3 activation. Changing the substituent groups (R groups) from dimethylphenol to ethylphenol in EMD or changing methylazanedyl to cyclohexylazanedyl in 24CD could only induce apoptosis activity but not autophagic inducing activity. We identified 24MD as a novel compound targeting autophagic cell death by affecting mTOR-mediated autophagy.

  自噬是消除受损细胞器和错误折叠蛋白质的多步骤机制。该机制具有先导性，可诱导细胞凋亡等其他程序的细胞死亡。本研究揭示了 24MD 在诱导肺癌细胞自噬方面的潜在药理作用。结果表明，24MD 可同时诱导自噬，自噬体染色和 ATG5、ATG7 的诱导以及泛素化蛋白 p62 的表达表明了这一点。处理 24 小时后，LC3-I 与 LC3-II 发生了强烈的对话，p62 则出现了下调。附件素 V-FITC/ 碘化丙啶染色和 caspase-3 激活表明，48 小时处理后发现了凋亡诱导活性。从机理角度来看，60 μM 的 24MD 处理 24 小时后会大幅下调 p-mTOR。同时，p-PI3K 和 p-Akt 也分别被浓度为 80 μM 和 100 μM 的 24MD 所抑制。我们通过 Western 印迹和免疫荧光检测，比较了 24MD 与雷帕霉素（一种强效的标准 mTOR1 抑制剂）的作用，进一步证实了 m-TOR 介导的自噬活性。虽然 24MD 对 p-mTOR 的抑制作用不如雷帕霉素，但雷帕霉素和 24MD 的联合使用可增强 mTOR 抑制活性和 LC3 活化。将 EMD 中的取代基（R 基）从二甲基苯酚改为乙基苯酚，或将 24CD 中的甲基氮杂环丁基改为环己基氮杂环丁基，只能诱导细胞凋亡活性，而不能诱导自噬活性。我们发现 24MD 是一种新型化合物，它通过影响 mTOR 介导的自噬作用来靶向自噬细胞死亡。
• Underwater coating composition
  申请人：ASTRAL Société de Peintures et Vernis

  公开号：EP0023371A1

  公开（公告）日：1981-02-04

  The present invention relates to a novel underwater coating composition which comprises a film forming resin, a complexing agent forming a complex with an oxidized iron surface and a non-reactive solvent which is partly soluble in water. This coating composition is suitable to be used, notably, for coating submerged structures.

  本发明涉及一种新型水下涂料组合物，它包括一种成膜树脂、一种与氧化铁表面形成络合物的络合剂和一种部分溶于水的非反应性溶剂。 这种涂料组合物适合用于水下结构的涂层。