N-morpholino-3-benzyloxyazetidinium bromide | 564485-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-morpholino-3-benzyloxyazetidinium bromide
• 英文别名: 2-phenylmethoxy-7-oxa-4-azoniaspiro[3.5]nonane;bromide
• CAS: 564485-69-4
• 化学式: Br*C₁₄H₂₀NO₂
• 分子量: 314.222
• InChiKey: CQPAPELCZKEESC-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.56
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Triethylammonium dineopentyl phosphorodithioate 、 N-morpholino-3-benzyloxyazetidinium bromide 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以80%的产率得到O,O-dineopentyl-S-(2-benzyloxy-3-N-morpholino)propyl phosphorodithioate
  参考文献：
  名称：

  氮杂环丁烷鎓离子和环氧化物介导的多官能二硫代硫代磷酸酯和结构类似物的合成

  摘要：

  N，N-二烷基-3-羟基（苄氧基）氮杂环丁烷鎓盐1和N，N-二苄基-2,3-环氧丙胺10与磷2的一硫代和二硫代酸阴离子的亲核开环反应生成二硫代磷酸酯（和结构类似物）3和11具有结合有2-羟基和3-二烷基氨基官能团的S-丙基取代基。讨论了这些化合物的稳定性对结构因素的强烈依赖性。

  DOI：

  10.1016/s0040-4039(03)00638-5
• 作为产物：
  描述：

  溴甲苯 、 N-(b-羟基三甲基)氯化吗啉 在 氢氧化钾 、 calcium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 14.0h， 生成 N-morpholino-3-benzyloxyazetidinium bromide
  参考文献：
  名称：

  Convenient synthesis of propane aminophosphonic acids, aminodiphosphonic acids and their structural analogues, mediated by azetidinium salts

  摘要：

  The reactions of azetidinium salts with phosphorus nucleophiles R2P(O)H have been investigated. Treatment of O-benzyl-N,N-diethyl-3-hydroxyazetidinium salt 2 with R2P(O)H in the presence of sodium hydride gave the corresponding gamma-N,N-diethylamino-beta-benzyloxypropylphosphonate 6a or phosphine oxide 6b. After debenzylation gamma-N,N-diethylamino-beta-hydroxypropylphosphonate 3a and phosphine oxide 3b were obtained. The compound 6a was converted into its sulfonate ester 8 which underwent elimination to yield 4. The structure 4 has been employed in Michael addition of R2P(O)H to form compounds 5 containing two phosphorus centers. Further compounds of type 3 have been transformed into compounds 5 by reaction with R2P(O)H in the presence of 1.1 equivalents of NaH in boiling toluene. Finally, azetidinium salts 1 have been converted into compounds 5a by reaction with two equivalents of R2P(O)H in the presence of 2.1 equivalents of NaH. Molecular mechanics with implementation of the Allinger MM2 force field and semiempirical AM1 and PM3 methods were used to investigate structures 5d and 5f. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00698-5

文献信息

• Synthesis of polyfunctional phosphorodithioates and structural analogues mediated by azetidinium ions and epoxides
  作者：Agata Jeziorna、Jan Heliński、Bożena Krawiecka

  DOI：10.1016/s0040-4039(03)00638-5

  日期：2003.4

  The nucleophilic ring opening reactions of N,N-dialkyl-3-hydroxy(benzyloxy)azetidinium salts 1 and N,N-dibenzyl-2,3-epoxypropylamine 10 with anions of mono- and dithioacids of phosphorus 2 affords phosphorodithioates (and structural analogues) 3 and 11 possessing S-propyl substituents incorporating 2-hydroxy and 3-dialkylamino functionalities. A strong dependence of the stability of these compounds

  N，N-二烷基-3-羟基（苄氧基）氮杂环丁烷鎓盐1和N，N-二苄基-2,3-环氧丙胺10与磷2的一硫代和二硫代酸阴离子的亲核开环反应生成二硫代磷酸酯（和结构类似物）3和11具有结合有2-羟基和3-二烷基氨基官能团的S-丙基取代基。讨论了这些化合物的稳定性对结构因素的强烈依赖性。
• Convenient synthesis of propane aminophosphonic acids, aminodiphosphonic acids and their structural analogues, mediated by azetidinium salts
  作者：A Bakalarz、J Heliński、B Krawiecka、J Michalski、M.J Potrzebowski

  DOI：10.1016/s0040-4020(99)00698-5

  日期：1999.10

  The reactions of azetidinium salts with phosphorus nucleophiles R2P(O)H have been investigated. Treatment of O-benzyl-N,N-diethyl-3-hydroxyazetidinium salt 2 with R2P(O)H in the presence of sodium hydride gave the corresponding gamma-N,N-diethylamino-beta-benzyloxypropylphosphonate 6a or phosphine oxide 6b. After debenzylation gamma-N,N-diethylamino-beta-hydroxypropylphosphonate 3a and phosphine oxide 3b were obtained. The compound 6a was converted into its sulfonate ester 8 which underwent elimination to yield 4. The structure 4 has been employed in Michael addition of R2P(O)H to form compounds 5 containing two phosphorus centers. Further compounds of type 3 have been transformed into compounds 5 by reaction with R2P(O)H in the presence of 1.1 equivalents of NaH in boiling toluene. Finally, azetidinium salts 1 have been converted into compounds 5a by reaction with two equivalents of R2P(O)H in the presence of 2.1 equivalents of NaH. Molecular mechanics with implementation of the Allinger MM2 force field and semiempirical AM1 and PM3 methods were used to investigate structures 5d and 5f. (C) 1999 Elsevier Science Ltd. All rights reserved.