1-butyl-3,4,5-triphenyl-1,2-diphosphacyclopenta-2,4-diene | 1262835-42-6

• 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: 1-butyl-3,4,5-triphenyl-1,2-diphosphacyclopenta-2,4-diene
• 英文别名: 1-Butyl-3,4,5-triphenyldiphosphole；1-butyl-3,4,5-triphenyldiphosphole
• CAS: 1262835-42-6
• 化学式: C₂₅H₂₄P₂
• 分子量: 386.413
• InChiKey: QLWPJIHZCYEJOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-butyl-3,4,5-triphenyl-1,2-diphosphacyclopenta-2,4-diene 在 N-叔丁基-α-苯基硝酮 作用下， 生成 5,10-Dibutyl-2,3,4,7,8,9-hexakis-phenyl-1,5lambda5,6,10lambda5-tetraphosphatricyclo[5.2.1.02,6]deca-3,8-diene 5,10-dioxide
  参考文献：
  名称：

  Versatile Cycloaddition Reactions of 1-Alkyl-1,2-Diphospholes

  摘要：

  The reactivity of 1-alkyl-1,2-diphospholes in cycloaddition reactions with dienes, dienophiles or 1,3-dipoles was examined. 1-Alkyl-1,2-diphospholes (2 ) exhibit dual reactivity and act as diene toward maleic acid derivatives or as dienophiles with 2,3-dimethyl-1,3-butadiene. The 1-alkenyl-1,2-diphospholes (4 )are readily involved in intramolecular [4 + 2] cycloaddition reactions leading to cage phosphines (5 ). Interaction of 1-alkyl-1,2-diphospholes (2) with 1,3-dipolar reagents (diphenyldiazomethane and nitrones) results in formation of the bicyclic phosphiranes (8) and dimers of 1-alkyl-1,2-diphosphole oxides (9) or bicyclic phosphine oxides (10) with a -lactam moiety depending on temperature.

  DOI：

  10.1080/10426507.2012.744017
• 作为产物：
  描述：

  sodium 3,4,5-triphenyl-1,2-diphosphacyclopentadienide 、 正溴丁烷 以 四氢呋喃 为溶剂， 反应 3.0h， 以59%的产率得到1-butyl-3,4,5-triphenyl-1,2-diphosphacyclopenta-2,4-diene
  参考文献：
  名称：

  3,4,5-三苯基-1,2-二磷杂环戊二烯钠与卤代烷和硅和氯化锡的反应

  摘要：

  3,4,5-三苯基-1,2-二磷酸环戊二烯钠与伯烷基溴、仲烷基碘以及硅和氯化锡的反应得到稳定的1-取代的1,2-二磷。在 3,4,5-triphenyl-1-trimethylstannyl-1,2-diphosphacyclopenta-2,4-diene 的溶液中，Me3Sn 基团在两个磷原子之间迁移。

  DOI：

  10.1007/s11172-010-0226-9

文献信息

• Cycloaddition reactions of 1-Alkyl-3,4,5-triphenyl-1,2-iphosphacyclopenta-2,4-dienes in the coordination sphere of tungsten carbonyl
  作者：V. A. Milyukov、A. A. Zagidullin、E. Hey-Hawkins、O. G. Sinyashin

  DOI：10.1134/s1070328410120043

  日期：2010.12

  1-Alkyl-3,4,5-triphenyl-1,2-diphosphacyclopenta-2,4-dienes react with tungsten hexacarbonyl under the conditions of “indirect” replacement of the carbonyl group to give 1: 1 complexes; [4+2] cycloaddition reactions of these complexes with maleic acid derivatives and substituted acetylenes afford tungsten carbonyl complexes containing 10-alkyl-1,10-diphosphatricyclo[5.2.1.02.6]deca-8-ene-3,5-diones

  在“间接”取代羰基的条件下，1-烷基-3,4,5-三苯基-1,2-二磷杂环戊-2,4-二烯与六羰基钨反应，形成1：1络合物；这些配合物与马来酸衍生物和取代的乙炔的[4 + 2]环加成反应得到羰基钨配合物，该配合物含有10-烷基-1,10-二磷三环[5.2.1.0 2.6 ] deca-8-ene-3,5-diones和1 -烷基-2，3-二苯基膦基。
• Reactions of 1-alkyl-1,2-diphospholes with 1,3-dipoles: diphenyldiazomethane and nitrones
  作者：Almaz Zagidullin、Yulia Ganushevich、Vasili Miluykov、Dmitry Krivolapov、Olga Kataeva、Oleg Sinyashin、Evamarie Hey-Hawkins

  DOI：10.1039/c2ob25532d

  日期：——

  The reaction of 1-alkyl-1,2-diphosphacyclopenta-2,4-dienes (1-alkyl-1,2-diphospholes) (1) with diphenyldiazomethane proceeds at room temperature via unstable [3+2] cycloadducts to form bicyclic phosphiranes (2). However, 1-alkyl-1,2-diphospholes (1) react with N,alpha-diphenylnitrone or N-tert-butyl-alpha-phenylnitrone depending on the temperature to give either dimers of 1-alkyl-1-oxo-1,2-diphospholes

  1-烷基-1,2-二磷酸环戊-2,4-二烯（1-烷基-1,2-二磷酸酯）（1）与二苯基重氮甲烷在室温下通过不稳定的[3 + 2]环加合物进行反应，形成双环膦（2）。然而，1-烷基-1,2-二磷酸酯（1）与N，α-二苯基硝基 或者 N-叔丁基-α-苯基硝基取决于温度给出1-烷基-1-氧代-1,2-二膦（5）的二聚体或1-烷基-1,7-二氧代-6-偶氮-1,7-二磷-双环[3.2]。 0]庚-2-烯（7）–β-内酰胺的磷类似物。
• Reactions of sodium 3,4,5-triphenyl-1,2-diphosphacyclopentadienide with alkyl halides and silicon and tin chlorides
  作者：V. A. Milyukov、I. A. Bezkishko、A. A. Zagidullin、O. G. Sinyashin、E. Hey-Hawkins

  DOI：10.1007/s11172-010-0226-9

  日期：2010.6

  Reactions of sodium 3,4,5-triphenyl-1,2-diphosphacyclopentadienide with primary alkyl bromides, secondary alkyl iodides, and silicon and tin chlorides gave stable 1-substituted 1,2-diphospholes. In a solution of 3,4,5-triphenyl-1-trimethylstannyl-1,2-diphosphacyclopenta-2,4-diene, the Me3Sn group migrates between two phosphorus atoms.

  3,4,5-三苯基-1,2-二磷酸环戊二烯钠与伯烷基溴、仲烷基碘以及硅和氯化锡的反应得到稳定的1-取代的1,2-二磷。在 3,4,5-triphenyl-1-trimethylstannyl-1,2-diphosphacyclopenta-2,4-diene 的溶液中，Me3Sn 基团在两个磷原子之间迁移。
• Versatile Cycloaddition Reactions of 1-Alkyl-1,2-Diphospholes
  作者：Almaz Zagidullin、Yulia Ganushevich、Vasili Miluykov、Oleg Sinyashin、Evamarie Hey-Hawkins

  DOI：10.1080/10426507.2012.744017

  日期：2013.1.1

  The reactivity of 1-alkyl-1,2-diphospholes in cycloaddition reactions with dienes, dienophiles or 1,3-dipoles was examined. 1-Alkyl-1,2-diphospholes (2 ) exhibit dual reactivity and act as diene toward maleic acid derivatives or as dienophiles with 2,3-dimethyl-1,3-butadiene. The 1-alkenyl-1,2-diphospholes (4 )are readily involved in intramolecular [4 + 2] cycloaddition reactions leading to cage phosphines (5 ). Interaction of 1-alkyl-1,2-diphospholes (2) with 1,3-dipolar reagents (diphenyldiazomethane and nitrones) results in formation of the bicyclic phosphiranes (8) and dimers of 1-alkyl-1,2-diphosphole oxides (9) or bicyclic phosphine oxides (10) with a -lactam moiety depending on temperature.