3-(succinimidomethyl)tetrahydro-1,3-oxazine | 309921-05-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(succinimidomethyl)tetrahydro-1,3-oxazine
• 英文别名: N-(tetrahydro-1,3-oxazinomethyl)succinimide；1-(1,3-oxazinan-3-ylmethyl)pyrrolidine-2,5-dione
• CAS: 309921-05-9
• 化学式: C₉H₁₄N₂O₃
• 分子量: 198.222
• InChiKey: CPGAWHMWZHOSAE-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±37.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(succinimidomethyl)tetrahydro-1,3-oxazine 在 硝酸 作用下， 反应 0.5h， 以60%的产率得到1-(5-nitroxy-2-azoniapentyl)pyrrolidine-2,5-dione nitrate
  参考文献：
  名称：

  新的 N-亚硝胺。2. 四氢-1,3-恶嗪转化为 N-亚硝基氨基醇的硝酸盐

  摘要：

  HNO3 与分别由二酮哌嗪、靛红和琥珀酰亚胺的氨甲基化产生的四氢-1,3-恶嗪 1a-c 反应，得到氨基醇的硝酸盐 [RCH2NH2(CH2)3ONO2]+NO3-(4a-c)，其随后的N-亚硝化（NaNO2，AcOH）得到 N-亚硝基氨基醇的硝酸盐 RCH2N(NO)(CH2)3ONO2 (5a-c)。化合物5b、c的结构通过X射线衍射分析确定。

  DOI：

  10.1023/b:rucb.0000011881.12055.58
• 作为产物：
  描述：

  丁二酰亚胺 、 聚合甲醛 、 3-氨基-1-丙醇 以 水 、 异丙醇 为溶剂， 反应 1.0h， 以76%的产率得到3-(succinimidomethyl)tetrahydro-1,3-oxazine
  参考文献：
  名称：

  摘要：

  The reactions of isatin. benzotriazole. and succinimide with formaldehyde and methylamine yield monoamines RCH2N(Me)CH2R and methylenediamines RCH2N(Me)CH2N(Me)CH2R. The use of ethylenediamine as the amino component affords N,N'-disubstituted imidazolidines, while the reactions with 3-aminopropan-1-ol give N-substituted tetrahydro-1,3-oxazines. RCH2NBu21 was obtained from succinimide. formaldehyde, and diisobutylamine. Nitrosative cleavage of the amines obtained was studied: it was shown that monoamines and methylenediamines give N-nitrosoamines RCH2N(NO)Me, which were structurally characterized by X-ray diffraction analysis, RCH2NBu21 affords diisobutylnitrosamine. while imidazolidines transform into dinitroso compounds RCH2N(NO)CH2CH2N(NO)CH2R.

  DOI：

  10.1023/a:1013094720611

文献信息

• ——
  作者：A. G. Korepin、P. V. Galkin、N. M. Glushakova、V. P. Lodygina、I. L. Eremenko、S. E. Nefedov、L. T. Eremenko

  DOI：10.1023/a:1013094720611

  日期：——

  The reactions of isatin. benzotriazole. and succinimide with formaldehyde and methylamine yield monoamines RCH2N(Me)CH2R and methylenediamines RCH2N(Me)CH2N(Me)CH2R. The use of ethylenediamine as the amino component affords N,N'-disubstituted imidazolidines, while the reactions with 3-aminopropan-1-ol give N-substituted tetrahydro-1,3-oxazines. RCH2NBu21 was obtained from succinimide. formaldehyde, and diisobutylamine. Nitrosative cleavage of the amines obtained was studied: it was shown that monoamines and methylenediamines give N-nitrosoamines RCH2N(NO)Me, which were structurally characterized by X-ray diffraction analysis, RCH2NBu21 affords diisobutylnitrosamine. while imidazolidines transform into dinitroso compounds RCH2N(NO)CH2CH2N(NO)CH2R.
• ——
  作者：A. G. Korepin、P. V. Galkin、N. M. Glushakova、G. V. Lagodzinskaya、M. V. Loginova、V. P. Lodygina、L. T. Eremenko

  DOI：10.1023/a:1009537504497

  日期：——

  A new version of the Mannich reaction involving amino alcohols (3-aminopropan-1-ol and aminoethanol) was developed. These compounds react with formaldehyde and CH or NH acids to give N-substituted tetrahydro-1,3-oxazines or oxazolidines.
• New N-nitrosoamines. 2. Transformations of tetrahydro-1,3-oxazines into nitrates of N-nitrosoamino alcohols
  作者：A. G. Korepin、P. V. Galkin、E. K. Perepelkina、N. M. Glushakova、V. P. Lodygina、I. L. Eremenko、S. E. Nefedov、L. T. Eremenko

  DOI：10.1023/b:rucb.0000011881.12055.58

  日期：2003.10

  The reactions of HNO3 with tetrahydro-1,3-oxazines 1a—c produced by aminomethylation of diketopiperazine, isatin, and succinimide, respectively, afforded nitrates of amino alcohols [RCH2NH2(CH2)3ONO2]+NO3– (4a—c) whose subsequent N-nitrosation (NaNO2, AcOH) gave nitrates of N-nitrosoamino alcohols RCH2N(NO)(CH2)3ONO2 (5a—c). The structures of compound 5b,c were established by X-ray diffraction analysis

  HNO3 与分别由二酮哌嗪、靛红和琥珀酰亚胺的氨甲基化产生的四氢-1,3-恶嗪 1a-c 反应，得到氨基醇的硝酸盐 [RCH2NH2(CH2)3ONO2]+NO3-(4a-c)，其随后的N-亚硝化（NaNO2，AcOH）得到 N-亚硝基氨基醇的硝酸盐 RCH2N(NO)(CH2)3ONO2 (5a-c)。化合物5b、c的结构通过X射线衍射分析确定。