1,1,1,4-tetraphenyl-3-(2-furyl)-2-aza-1,λ⁵-phosphabuta-1,3-diene | 185623-64-7

• 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: 1,1,1,4-tetraphenyl-3-(2-furyl)-2-aza-1,λ⁵-phosphabuta-1,3-diene
• 英文别名: 1,1,1,4-tetraphenyl-3-(2-furyl)-2-aza-1λ⁵-phosphabuta-1,3-diene；[(Z)-1-(furan-2-yl)-2-phenylethenyl]imino-triphenyl-lambda5-phosphane；[(Z)-1-(furan-2-yl)-2-phenylethenyl]imino-triphenyl-λ5-phosphane
• CAS: 185623-64-7
• 化学式: C₃₀H₂₄NOP
• 分子量: 445.5
• InChiKey: MCUQHOUXQAFTTG-OLFWJLLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,1,1,4-tetraphenyl-3-(2-furyl)-2-aza-1,λ⁵-phosphabuta-1,3-diene 在 lithium perchlorate 作用下， 以 乙醚 、 氯仿 为溶剂， 反应 18.0h， 生成 diethyl (2S,5R)-4-(furan-2-yl)-5-phenyl-2-pyridin-3-yl-2,5-dihydro-1,3-oxazine-6,6-dicarboxylate
  参考文献：
  名称：

  Aza-Wittig Reaction of N-Vinylic Phosphazenes with Carbonyl Compounds. Azadiene-Mediated Synthesis of Isoquinolines and 5,6-Dihydro-2H-1,3-oxazines

  摘要：

  N-Vinylic phosphazenes 4 are obtained by reaction of phosphorus ylide 5 and nitriles 6. Aza-Wittig reaction of phosphazenes 4 with aldehydes leads to the formation of 2-azadienes 1, which are easily converted into isoquinolines 2. Reaction of conjugated phosphazenes 4 with ethyl glyoxalate affords 5,6-dihydro-2H-1,3-oxazines 9 in a regio- and stereoselective fashion, while heterodienes 1 react with ethyl glyoxalate and diethyl ketomalonate giving 1,3-oxazines 11 and 12.

  DOI：

  10.1021/jo961664n
• 作为产物：
  描述：

  2-氰基呋喃 、 苄基三苯基鏻碘化物 在 甲基锂 作用下， 生成 1,1,1,4-tetraphenyl-3-(2-furyl)-2-aza-1,λ⁵-phosphabuta-1,3-diene
  参考文献：
  名称：

  Aza-Wittig Reaction of N-Vinylic Phosphazenes with Carbonyl Compounds. Azadiene-Mediated Synthesis of Isoquinolines and 5,6-Dihydro-2H-1,3-oxazines

  摘要：

  N-Vinylic phosphazenes 4 are obtained by reaction of phosphorus ylide 5 and nitriles 6. Aza-Wittig reaction of phosphazenes 4 with aldehydes leads to the formation of 2-azadienes 1, which are easily converted into isoquinolines 2. Reaction of conjugated phosphazenes 4 with ethyl glyoxalate affords 5,6-dihydro-2H-1,3-oxazines 9 in a regio- and stereoselective fashion, while heterodienes 1 react with ethyl glyoxalate and diethyl ketomalonate giving 1,3-oxazines 11 and 12.

  DOI：

  10.1021/jo961664n

文献信息

• Reactions of N-vinylic phosphazenes with azodicarboxylic and acetylenic esters
  作者：Francisco Palacios、Concepción Alonso、Gloria Rubiales、Jose Marı́a Ezpeleta

  DOI：10.1016/j.tet.2004.01.052

  日期：2004.3

  N-Vinylic phosphazenes react as enamines (1,4-addition) with azodicarboxylic esters, whereas different behavior is observed when these phosphazenes react with dimethyl acetylenedicarboxylate (3,4-addition). A [2+2] cycloaddition reaction of the vinyl moiety of vinylic phosphazenes with the acetylenic triple bond of the acetylenic esters followed by a ring opening leads to the formation of functionalized conjugated

  N-乙烯基磷腈作为烯胺（1,4-加成）与偶氮二羧酸酯反应，而当这些磷腈与乙炔二羧酸二甲酯（3,4-加成）反应时，观察到不同的行为。乙烯基磷腈的乙烯基部分与炔属酯的炔三键的[2 + 2]环加成反应随后开环导致形成官能化的共轭磷腈。
• Reaction of acetylenic esters and N-functionalized phosphazenes. 1,2- versus 1,4-addition of N-vinylic phosphazenes
  作者：Francisco Palacios、Concepción Alonso、Jaione Pagalday、Ana María Ochoa de Retana、Gloria Rubiales

  DOI：10.1039/b212693a

  日期：2003.3.27

  Reaction of phosphazenes derived from aminophosphonates with acetylenic esters leads to conjugated phosphorus ylides. The formation of these stabilized ylides is explained through a [2 + 2] cycloaddition reaction of the P = N linkage of the phosphazene (1,2-addition) and the triple bond of the acetylenic ester followed by ring opening of the azaphosphete intermediate. However, in the case of N-vinylic

  衍生自氨基膦酸酯的磷腈与炔属酯的反应导致共轭磷酰化。通过磷腈的P = N键（1,2-加成）和炔属酯的三键的[2 + 2]环加成反应，然后再进行氮杂磷中间体的开环，可以解释这些稳定化亚烷基的形成。然而，在N-乙烯基磷腈的情况下，衍生自三苯基膦和三甲基膦的磷腈与二乙炔酸酯反应为烯胺（1,4-加成），而在衍生自三甲基膦的磷腈中，丙酸乙酯1,2-加成产生磷腈的P ＝ N键。
• Aza-Wittig Reaction of <i>N</i>-Vinylic Phosphazenes with Carbonyl Compounds. Azadiene-Mediated Synthesis of Isoquinolines and 5,6-Dihydro-2<i>H</i>-1,3-oxazines
  作者：Francisco Palacios、Concepción Alonso、Gloria Rubiales

  DOI：10.1021/jo961664n

  日期：1997.2.1

  N-Vinylic phosphazenes 4 are obtained by reaction of phosphorus ylide 5 and nitriles 6. Aza-Wittig reaction of phosphazenes 4 with aldehydes leads to the formation of 2-azadienes 1, which are easily converted into isoquinolines 2. Reaction of conjugated phosphazenes 4 with ethyl glyoxalate affords 5,6-dihydro-2H-1,3-oxazines 9 in a regio- and stereoselective fashion, while heterodienes 1 react with ethyl glyoxalate and diethyl ketomalonate giving 1,3-oxazines 11 and 12.