2-甲基-1,3-二氢苯并[f][1,3]苯并恶嗪 | 35141-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 2-甲基-1,3-二氢苯并[f][1,3]苯并恶嗪
• 英文名称: 2-methyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine
• 英文别名: N-methyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine；2-methyl-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazine；2-methyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazine；2-Methyl-2,3-dihydro-1H-naphth[1,2-e][1,3]oxazin；2-Methyl-2,3-dihydro-1H-naphth<1,2-e><1,3>oxazin；2-Methyl-1.2-dihydro-3H-naphth<1.2-e>-1.3-oxazin；2-methyl-1,3-dihydrobenzo[f][1,3]benzoxazine
• CAS: 35141-64-1
• 化学式: C₁₃H₁₃NO
• mdl: MFCD01426764
• 分子量: 199.252
• InChiKey: MYKQUUUIXIFUMT-UHFFFAOYSA-N

物化性质

• 熔点：
  67-68 °C(Solv: methanol (67-56-1))
• 沸点：
  329.4±21.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  2-甲基-1,3-二氢苯并[f][1,3]苯并恶嗪 在 boron trioxide 作用下， 以 苯 为溶剂， 反应 12.0h， 生成 cis-N-methyl-1-(2-hydroxyethoxy)-bis(naphthyl)[2,1-c:1,2-h]-10-aza-1-bora-2,18-dioxabicyclooctane
  参考文献：
  名称：

  Synthesis of dioxazaborocines from N-substituted-bis(2-hydroxyaryl)aminomethylamines

  摘要：

  The preparation of a number of tripodal amines from aminoalkylation of 1,3-benzoxazines by phenols is presented. A series of ligands prepared in this manner were successfully coordinated to boron, giving dioxazaborocines. X-ray crystal structures of two analogues are reported. These compounds are capable of releasing berate ions and are therefore potentially biologically active. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00510-0
• 作为产物：
  描述：

  聚合甲醛 、 2-萘酚 在 甲醇 、 甲胺 作用下， 生成 2-甲基-1,3-二氢苯并[f][1,3]苯并恶嗪
  参考文献：
  名称：

  Condensation of Naphthols with Formaldehyde and Primary Amines¹

  摘要：

  DOI：

  10.1021/ja01134a039

文献信息

• Oxidative ortho-amino-methylation of phenols via C–H and C–C bond cleavage
  作者：Wenbo Sun、Huacan Lin、Wenyu Zhou、Zigang Li

  DOI：10.1039/c3ra46373g

  日期：——

  Initiated by CCl3Br, phenols undergo efficient ortho-selective oxidative cross dehydrogenative coupling (CDC) with trimethylamine. When tetramethylethylenediamine (TMEDA) is used instead of trimethylamine, oxidative carbon–carbon activation coupling (CAC) could occur to give the same salicylamines together with CDC by-products. These reactions are accelerated by a gold salt.

  在 CCl3Br 的作用下，苯酚与三甲胺发生高效的正选择性氧化交叉脱氢偶联（CDC）。当使用四甲基乙二胺（TMEDA）代替三甲胺时，可发生氧化碳-碳活化偶联（CAC），生成相同的水杨胺和 CDC 副产物。金盐可加速这些反应。
• Novel synthesis of aminoacetonitriles via the selective demethylation of quaternary ammonium salts
  作者：Evgeny M. Buev、Anastasia A. Smorodina、Maxim A. Stepanov、Vladimir S. Moshkin、Vyacheslav Y. Sosnovskikh

  DOI：10.1016/j.tetlet.2018.03.037

  日期：2018.4

  amines readily formed quaternary ammonium salts upon treatment with iodoacetonitrile in high yields (70–96%). The latter were selectively demethylated by heating in dimethylformamide to give aminoacetonitriles in moderate to good overall yields (36–69%).

  用碘乙腈处理后，N-甲基环胺很容易形成季铵盐（70-96％）。后者通过在二甲基甲酰胺中加热选择性脱甲基，得到氨基乙腈，总收率中等至良好（36-69％）。
• Lockhart, Joyce C.; McDonnell, Martin B.; Tyson, Philip D., Journal of the Chemical Society. Perkin transactions I, 1983, p. 2153 - 2160
  作者：Lockhart, Joyce C.、McDonnell, Martin B.、Tyson, Philip D.

  DOI：——

  日期：——
• A novel method for functionalising resorcinarenes
  作者：Paul D. Woodgate、Gillian M. Horner、N.Paul Maynard

  DOI：10.1016/s0040-4039(99)01338-6

  日期：1999.8

  Tetra-N-methyl(2-hydroxynaphthylmethyl)aminomethyl resorcinarene 5 has been synthesised either from tetrabenzoxazine resorcinarene 2 and 2-naphthol or from the C-methyl resorcinarene 1 and naphthoxazine 6. Reaction of the tetrabenzoxazine resorcinarene 2 with C-methyl resorcinarene 1 is proposed to give carceplex 7. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Synthesis and cardiovascular evaluation of N-substituted 1-aminomethyl-2-naphthols
  作者：A Shen

  DOI：10.1016/s0223-5234(99)00204-4

  日期：1999.10

  A series of 1-alkylaminomethylnaphthols have been prepared. These compounds were readily prepared in good yields by addition of 2-naphthol to formalin and alkylamines. The hypotensive and bradycardiac effects of these compounds in normotensive rats as well as their in vitro inotropic and aortic contraction effects in isolated rat left atria and aorta have been evaluated. A higher depressor and bradycardiac activity was found for compounds substituted on nitrogen by naphthol with primary amines, i.e., ethylamine, propylamine, isopropylamine, or butylamine and with a cyclic secondary amine, i.e., pyrrolidinyl. These compounds produced biphasic changes in contractile force in isolated rat atria which was correlated to blood pressure and heart rate activity. 1-Isopropylaminomethyl-2-naphthol hydrochloride relaxed isolated rat aortic rings precontracted with high extracellular K+ (80 mM) and Ca2+ (1.9 mM). The suppressive effects of the compounds may involve a direct inhibition of Ca2+ channels. The biological activity of these compounds can be explained in terms of substitution on nitrogen. (C) 1999 Editions scientifiques et medicales Elsevier SAS.