1,4-Bis(diphenylphosphorylmethyl)phthalazine | 1256393-46-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1,4-Bis(diphenylphosphorylmethyl)phthalazine
• 英文别名: 1,4-bis(diphenylphosphorylmethyl)phthalazine
• CAS: 1256393-46-0
• 化学式: C₃₄H₂₈N₂O₂P₂
• 分子量: 558.556
• InChiKey: FTQMSRTVXJYSJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-Bis(diphenylphosphorylmethyl)phthalazine 在 三氯硅烷 、 三乙胺 作用下， 以 甲苯 为溶剂， 以51%的产率得到1,4-bis((diphenylphosphino)methyl)phthalazine
  参考文献：
  名称：

  Dirhodium Complexes Bridged by Bis(diphenylphosphino)phthalazine (PNNP^Ph): Central Ring Size and Charge Effects As Compared with the Pyrazolate Derivative (PNNP^Py)

  摘要：

  A dirhodium carbonyl complex with 1,4-bis((diphenylphosphino)methyl)phthalazine (PNNPPh), [(mu-k(2):k(2)-PNNPPh){Rh(CO)(2)}(2)](BF4)(2), has been prepared and its reactivity studied as compared with the previously reported 3,5-bis((diphenylphosphino)methyl)pyrazolate (PNNPPy) analogue [(mu-k(2):k(2)-PNNPPy){Rh(CO)(2)}(2)]BF4. The two quadridentate ligands are different in the size of the central ring and the charge; six-membered ring/neutral (PNNPPh) vs five-membered ring/mononegative (PNNPPy). The reactivities of the two systems turn out to be very similar, as can be seen from formation of the analogous, unique tetranuclear mu(4)-acetylide ([(mu-PNNPPh)(2){Rh(CO)}(4)(mu(4)-C C-p-tol)]BF4) and mu(4)-dicarbidc complexes ([(mu-PNNPPh)(2){Rh(CO)}(4)(mu(4)-C-2)](BF4)(2)). However, the PNNPPh system exhibits the following features. (I) The enlargement of the central ring causes shortening of the metal-metal distance, frequently leading to bond formation between them. For more positively charged PNNPPh species, (2) back-donation decreases to facilitate CO dissociation and (3) the rhodium centers become more Lewis acidic. Another feature is that the PNNPPh complex undergoes oxidative addition upon treatment with internal alkynes to form stable adducts with unique coordination structures (e.g., 1,4-dimetallacyclohexa-2,5-diene).

  DOI：

  10.1021/om100832z
• 作为产物：
  描述：

  1,4-二氯酞嗪 、 甲基锂 、 三苯基氧化膦 以 乙醚 、 四氢呋喃 为溶剂， 反应 2.0h， 以60%的产率得到1,4-Bis(diphenylphosphorylmethyl)phthalazine
  参考文献：
  名称：

  Dirhodium Complexes Bridged by Bis(diphenylphosphino)phthalazine (PNNP^Ph): Central Ring Size and Charge Effects As Compared with the Pyrazolate Derivative (PNNP^Py)

  摘要：

  A dirhodium carbonyl complex with 1,4-bis((diphenylphosphino)methyl)phthalazine (PNNPPh), [(mu-k(2):k(2)-PNNPPh){Rh(CO)(2)}(2)](BF4)(2), has been prepared and its reactivity studied as compared with the previously reported 3,5-bis((diphenylphosphino)methyl)pyrazolate (PNNPPy) analogue [(mu-k(2):k(2)-PNNPPy){Rh(CO)(2)}(2)]BF4. The two quadridentate ligands are different in the size of the central ring and the charge; six-membered ring/neutral (PNNPPh) vs five-membered ring/mononegative (PNNPPy). The reactivities of the two systems turn out to be very similar, as can be seen from formation of the analogous, unique tetranuclear mu(4)-acetylide ([(mu-PNNPPh)(2){Rh(CO)}(4)(mu(4)-C C-p-tol)]BF4) and mu(4)-dicarbidc complexes ([(mu-PNNPPh)(2){Rh(CO)}(4)(mu(4)-C-2)](BF4)(2)). However, the PNNPPh system exhibits the following features. (I) The enlargement of the central ring causes shortening of the metal-metal distance, frequently leading to bond formation between them. For more positively charged PNNPPh species, (2) back-donation decreases to facilitate CO dissociation and (3) the rhodium centers become more Lewis acidic. Another feature is that the PNNPPh complex undergoes oxidative addition upon treatment with internal alkynes to form stable adducts with unique coordination structures (e.g., 1,4-dimetallacyclohexa-2,5-diene).

  DOI：

  10.1021/om100832z