1,3-dimethyl-2-pyrrolidin-1-yl-1,3,2-diazaphospholidine | 7137-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,3-dimethyl-2-pyrrolidin-1-yl-1,3,2-diazaphospholidine
• 英文别名: 1,3-dimethyl-2-pyrrolidin-1-yl-[1,3,2]diazaphospholidine；1,3-dimethyl-2-(1-pyrrolidinyl)-1,3,2-diazaphospholidine；1,3-Dimethyl-2-N-pyrrolidinyl-1,3-diaza-2-phospholan；2-N-Pyrrolidino-1,3-dimethyl-1,3,2-diazaphospholan；2-Pyrrolidino-1,3-dimethyl-1,3,2-diazaphospholan；1,3-Dimethyl-2-(pyrrolidin-1-yl)-1,3,2-diazaphospholidine
• CAS: 7137-84-0
• 化学式: C₈H₁₈N₃P
• 分子量: 187.225
• InChiKey: FAMNIJOYSZWUHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-2-pyrrolidin-1-yl-1,3,2-diazaphospholidine 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  1,3-Dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate (MNTP): a powerful condensing reagent for phosphate and phosphonate esters

  摘要：

  A novel phosphonium-type condensing reagent, 1,3-dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate (MNTP), was designed and synthesized. A P-31 NMR study oil the condensation reactions of phosphate, alkylphosphonate , boranophosphate, and H-phosphonate derivatives with an alcohol in the presence of MNTP demonstrated the versatility and the enhanced activity of the new condensing reagent, compared to the previously reported phosphonium-type condensing reagents. The mechanism of the condensation reactions mediated by MNTP is discussed on the basis of the P-31 NMR studies and theoretical calculations. (c) 2006 Elsevier Ltd. All rights, reserved.

  DOI：

  10.1016/j.tet.2006.01.084
• 作为产物：
  描述：

  1-三甲硅基吡咯烷 、 2-chloro-1,3-dimethyl-1,3,2-diazaphospholidine 反应 1.0h， 以94%的产率得到1,3-dimethyl-2-pyrrolidin-1-yl-1,3,2-diazaphospholidine
  参考文献：
  名称：

  1,3-Dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate (MNTP): a powerful condensing reagent for phosphate and phosphonate esters

  摘要：

  A novel phosphonium-type condensing reagent, 1,3-dimethyl-2-(3-nitro-1,2,4-triazol-1-yl)-2-pyrrolidin-1-yl-1,3,2-diazaphospholidinium hexafluorophosphate (MNTP), was designed and synthesized. A P-31 NMR study oil the condensation reactions of phosphate, alkylphosphonate , boranophosphate, and H-phosphonate derivatives with an alcohol in the presence of MNTP demonstrated the versatility and the enhanced activity of the new condensing reagent, compared to the previously reported phosphonium-type condensing reagents. The mechanism of the condensation reactions mediated by MNTP is discussed on the basis of the P-31 NMR studies and theoretical calculations. (c) 2006 Elsevier Ltd. All rights, reserved.

  DOI：

  10.1016/j.tet.2006.01.084

文献信息

• Reactivity of Cationic Phosphenium Complexes of Molybdenum:  Migration of OR, SR, and NR₂ on a Tertiary Phosphorus Compound to a Phosphenium Ligand
  作者：Yoshitaka Yamaguchi、Hiroshi Nakazawa、Mitsuru Kishishita、Katsuhiko Miyoshi

  DOI：10.1021/om9600304

  日期：1996.10.15

  The reaction of a cationic monoaminomonoalkoxy phosphenium complex of Mo, mer-[(bpy)(CO)3MoPN(Me)CH2CH2O}]+ (1a), with a diamino-substituted phosphorus compound, PN(Me)CH2CH2NMe(Y) (Y = OMe, OEt, SEt, N(CH2)3CH2), proceeds with substitution for CO and then with the Y group migration to the coordinating phosphenium phosphorus to give [(bpy)(CO)2PN(Me)CH2CH2O(Y)}MoPN(Me)CH2CH2NMe}]+ (2), which is

  Mo，mer -[（bpy）（CO）3 Mo PN（Me）CH 2 CH 2 O}] +（1a）的阳离子单氨基单烷氧基配合物与二氨基取代的磷化合物PN（Me ）CH 2 CH 2 NMe（Y）（Y = OMe，OEt，SEt，N（CH 2）3 CH 2），继续进行CO取代，然后将Y基团迁移至配位磷，得到[（bpy ）（CO）2 PN（Me）CH 2 CH 2 O（Y）} Mo PN（Me）CH 2 CH 2 NMe}] +（2），也由Mo，mer -[[（bpy）（CO）3 Mo PN（Me）CH 2 CH 2 NMe}] +（1b）的阳离子二氨基配合物和单氨基取代的磷化合物制得PN（Me）CH 2 CH 2 O（Y），通过简单的CO / PN（Me）CH 2 CH 2 O（Y）取代即可。这种迁移反应是不可逆的。还讨论了迁移机制。
• Reactions of five-membered cyclic triaminophosphines with hexafluoroacetone, trifluoroacetophenone, and fluorenone. Attack by phosphorus on carbonyl oxygen and isolation of crystalline 2,2,2-triamino-1,3,2-dioxaphospholanes
  作者：Fausto. Ramirez、Amar S. Gulati、Curtis Page. Smith

  DOI：10.1021/ja01000a052

  日期：1967.11
• Reaction of tertiary phosphines with hexafluoroacetone and with o-quinones. Attack by phosphorus on carbonyl oxygen and isolation of 2,2,2-trialkyl-2,2-dihydro-1,3,2-dioxaphospholanes
  作者：Fausto Ramirez、C. P. Smith、J. F. Pilot、A. S. Gulati

  DOI：10.1021/jo01274a023

  日期：1968.10
• Chemical Synthesis of Oligodeoxyribonucleotides Using <i>N</i>-Unprotected <i>H</i>-Phosphonate Monomers and Carbonium and Phosphonium Condensing Reagents:  <i>O</i>-Selective Phosphonylation and Condensation
  作者：Takeshi Wada、Yuichi Sato、Fumio Honda、Shun-ichi Kawahara、Mitsuo Sekine

  DOI：10.1021/ja9726015

  日期：1997.12.1

  Oligodeoxyribonucleotides were synthesized using H-phosphonate monomers without amino protection. The H-phosphonate monomers of deoxyadenosine, deoxycytidine, and deoxyguanosine bearing the free amino groups were synthesized in good yields by O-selective phosphonylation of the parent 5'-O-(dimethoxytrityl)deoxyribonucleosides. It was found that the amino groups of the nucleosides were not modified during internucleotidic bond formation where (benzotriazol-1-yloxy)carbonium and -phosphonium compounds were employed as condensing reagents. The most effective condensing reagent for rapid internucleotidic bond formation was found to be 2-(benzotriazol-1-yloxy)-1,1-dimethyl-2-hexafluorophosphate (BOMP). In the present H-phosphonate method, 2-(phenylsulfonyl)-3-(3-nitrophenyl)oxaziridine (PNO) was employed as a new oxidizing reagent for the oxidation of internucleotidic H-phosphonate linkages under anhydrous conditions in the presence of N,O-bis(trimethylsilyl)acetamide. The reaction mechanism for the O-selective condensation was investigated in detail by means of P-31 NMR spectroscopy. Unprecedented oxidation of the H-phosphonate monomers was observed during activation of the monomers with (benzotriazol-1-yloxy)phosphonium and -carbonium condensing reagents in the absence of the 5'-hydroxyl components. A mechanism for the O-selective condensation was proposed on the basis of ab initio molecular orbital calculations for the model compounds at the HF/6-31G* level.
• Isolation of a thiaminodioxyphosphorane and of the corresponding thriaminooxyphosphonium dipolar ion and demonstration of their equilibration in solution
  作者：Fausto Ramirez、A.V. Patwardhan、H.J. Kugler、C.P. Smith

  DOI：10.1016/s0040-4039(01)99912-5

  日期：——