1,3,2-diazaphospholidine-2-methyl-1,3-dimethyl 2-oxide | 16606-18-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 1,3,2-diazaphospholidine-2-methyl-1,3-dimethyl 2-oxide
• 英文别名: 1,2,3-Trimethyl-2-oxo-1,3,2-diazaphospholidin；1,2,3-trimethyl-1,3,2-diazaphospholidine-2-oxide；1,3,2-Diazaphospholidine, 1,2,3-trimethyl-, 2-oxide；1,2,3-trimethyl-1,3,2λ5-diazaphospholidine 2-oxide
• CAS: 16606-18-1
• 化学式: C₅H₁₃N₂OP
• 分子量: 148.145
• InChiKey: QBMPOGBYHHUSIF-UHFFFAOYSA-N

物化性质

• 熔点：
  41 °C
• 沸点：
  85-86 °C(Press: 1 Torr)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,2-diazaphospholidine-2-methyl-1,3-dimethyl 2-oxide 、 4-叔丁基环己酮 在 正丁基锂 作用下， 生成 1-叔丁基-4-亚甲基环己烷
  参考文献：
  名称：

  Efficient Olefinaton with a-Alkyl Cyclic Phosphonamides

  摘要：

  A variety of acyclic and cyclic aldehydes and ketones can be converted into the corresponding alkylidene, benzylidene and methoxycarbonyl alkylidene derivatives by treatment with 1,3,2-diazaphospholidine-2-alkyl-1,3-dimethyl 2-oxides (alpha-alkyl cyclic phosphonamides) under mild conditions. This olefination method is particularly useful in the case of enolizable carbonyl compounds.

  DOI：

  10.3987/com-93-s(t)145
• 作为产物：
  描述：

  甲基膦酞二氯 、 N,N'-二甲基乙二胺 在 三乙胺 作用下， 以 苯 为溶剂， 反应 1.5h， 以66%的产率得到1,3,2-diazaphospholidine-2-methyl-1,3-dimethyl 2-oxide
  参考文献：
  名称：

  Efficient Olefinaton with a-Alkyl Cyclic Phosphonamides

  摘要：

  A variety of acyclic and cyclic aldehydes and ketones can be converted into the corresponding alkylidene, benzylidene and methoxycarbonyl alkylidene derivatives by treatment with 1,3,2-diazaphospholidine-2-alkyl-1,3-dimethyl 2-oxides (alpha-alkyl cyclic phosphonamides) under mild conditions. This olefination method is particularly useful in the case of enolizable carbonyl compounds.

  DOI：

  10.3987/com-93-s(t)145

文献信息

• A divergent synthesis of minor groove binders with tail group variation
  作者：David Breen、Alan R. Kennedy、Colin J. Suckling

  DOI：10.1039/b814452d

  日期：——

  A new synthesis of polyamide minor groove binders in which diversity is introduced by the nucleophilic substitution of a 2-sulfido-1,3,2-diazaphospholidinyloxy substituent by volatile secondary amine nucleophiles is described. Such a method has potential value for economically investigating structure–activity relationships in this important class of compounds through library synthesis. As an example using this method are prepared two new minor groove binders with pyrrolidinyl or piperidinyl tail groups that are close relatives of highly active antibacterial minor groove binders with morpholinyl tail groups. The antibacterial activity found against Staphylococcus aureus and Mycobacterium spp. indicates that the pKa of this set of compounds is not the dominant factor in determining the antibacterial activity.

  描述了一种新的聚酰胺小沟结合剂的合成方法，该方法通过挥发性的二级胺亲核试剂对2-硫代-1,3,2-二氮杂膦啉氧取代基进行亲核取代，从而引入了多样性。这种方法在经济上研究这一重要化合物类的结构-活性关系方面具有潜在价值，通过文库合成进行探讨。作为这种方法的一个例子，合成了两种新的小沟结合剂，分别具有吡咯烷基或哌啶基尾部，它们与带有吗啉基尾部的高活性抗菌小沟结合剂密切相关。针对金黄色葡萄球菌和分枝杆菌群体的抗菌活性表明，这类化合物的pKa并不是决定抗菌活性的主导因素。
• 1,3-dimethyl 2-oxo 1,3,2-diazaphospholidine precursor of (Z) α,β-unsaturated esters.
  作者：Carl Patois、Philippe Savignac

  DOI：10.1016/s0040-4039(00)79655-9

  日期：1991.3

  alpha,beta-Unsaturated esters of (Z) geometry are selectively obtained from cyclic phosphonocarboxylates derived from N,N'-dimethylethylenediamine.
• PATOIS, CARL;SAVIGNAC, PHILIPPE, HETEROATOM CHEM., 1,(1990) N, C. 369-374
  作者：PATOIS, CARL、SAVIGNAC, PHILIPPE

  DOI：——

  日期：——
• Efficient Olefinaton with a-Alkyl Cyclic Phosphonamides
  作者：Stephen Hanessian、Youssef L. Bennani、Yves Leblanc

  DOI：10.3987/com-93-s(t)145

  日期：——

  A variety of acyclic and cyclic aldehydes and ketones can be converted into the corresponding alkylidene, benzylidene and methoxycarbonyl alkylidene derivatives by treatment with 1,3,2-diazaphospholidine-2-alkyl-1,3-dimethyl 2-oxides (alpha-alkyl cyclic phosphonamides) under mild conditions. This olefination method is particularly useful in the case of enolizable carbonyl compounds.

表征谱图