dphpn | 73892-41-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: dphpn
• 英文别名: 1,8-bis[(diphenylphosphino)methyl]naphthalene；[8-(Diphenylphosphanylmethyl)naphthalen-1-yl]methyl-diphenylphosphane
• CAS: 73892-41-8
• 化学式: C₃₆H₃₀P₂
• 分子量: 524.582
• InChiKey: SLDSMPQCEMKGEY-UHFFFAOYSA-N

物化性质

• 沸点：
  671.1±48.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  38
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  RuH₂(CO)(PPh₃)₃ 、 dphpn 以 甲苯 为溶剂， 以72%的产率得到Ru(H)2(CO)(PPh3)(1,8-bis(diphenylphosphinomethyl)naphthalene) dihydrate
  参考文献：
  名称：

  Synthesis and characterization of ruthenium complexes of 1,8-bis(diphenylphosphinomethyl)naphthalene (BDNA) and their catalytic hydrogenation reactions to α,β-unsaturated aldehydes

  摘要：

  A new ligand BDNA [1,8-bis(diphenylphosphinomethyl)naphthalene] and three ruthenium complexes containing the new ligand, Ru2Cl4(BDNA)(2) 1, RuHCl(CO)(PPh3)(BDNA) 2, and RuH2(CO)(PPh3)(BDNA) 3, have been synthesized. Their compositions and structures were characterized by P-31{H-1}-NMR, H-1-NMR, and elemental analysis. Molecular structure of 3 was also confirmed by single-crystal X-ray diffraction. The crystal belonged to the triclinic crystal system, P (1) over bar space group, a = 10.7450(7), b = 12.7100(7), c = 18.1390(13) Angstrom, alpha = 89.558(6), beta = 83.117(2), gamma = 80.859(5)degrees, V = 2428.0(3) Angstrom(3), and Z = 2. The hydrogenation results of citral and cinnamaldehyde revealed that complex 2 had good catalytic activity and complex 3 had the high selectivity for the hydrogenation of C=O bond in alpha,beta-unsaturated aldehydes to form the corresponding allylic alcohols. In the presence of complex 3, very high selectivities of 99.5 and 95.1% were obtained for the hydrogenation of the carbonyl group in citral and cinnamaldehyde, respectively. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00889-4
• 作为产物：
  描述：

  1,8-双(溴甲基)萘 、 三苯基膦 在 氯代叔丁烷 、 lithium 作用下， 生成 dphpn
  参考文献：
  名称：

  Synthesis and characterization of ruthenium complexes of 1,8-bis(diphenylphosphinomethyl)naphthalene (BDNA) and their catalytic hydrogenation reactions to α,β-unsaturated aldehydes

  摘要：

  A new ligand BDNA [1,8-bis(diphenylphosphinomethyl)naphthalene] and three ruthenium complexes containing the new ligand, Ru2Cl4(BDNA)(2) 1, RuHCl(CO)(PPh3)(BDNA) 2, and RuH2(CO)(PPh3)(BDNA) 3, have been synthesized. Their compositions and structures were characterized by P-31{H-1}-NMR, H-1-NMR, and elemental analysis. Molecular structure of 3 was also confirmed by single-crystal X-ray diffraction. The crystal belonged to the triclinic crystal system, P (1) over bar space group, a = 10.7450(7), b = 12.7100(7), c = 18.1390(13) Angstrom, alpha = 89.558(6), beta = 83.117(2), gamma = 80.859(5)degrees, V = 2428.0(3) Angstrom(3), and Z = 2. The hydrogenation results of citral and cinnamaldehyde revealed that complex 2 had good catalytic activity and complex 3 had the high selectivity for the hydrogenation of C=O bond in alpha,beta-unsaturated aldehydes to form the corresponding allylic alcohols. In the presence of complex 3, very high selectivities of 99.5 and 95.1% were obtained for the hydrogenation of the carbonyl group in citral and cinnamaldehyde, respectively. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00889-4

文献信息

• 烯烃氢甲酰化制备醛的方法
  申请人：上海华谊（集团）公司

  公开号：CN105566081A

  公开（公告）日：2016-05-11

  本发明涉及一种烯烃氢甲酰化制备醛的方法，主要解决现有技术中产品中正异比较低、催化剂稳定性差的问题。本发明通过采用一种烯烃氢甲酰化制备醛的方法，在烯烃氢甲酰化反应中，催化剂为络合催化剂Ⅰ或络合催化剂Ⅱ中的至少一种的技术方案较好地解决了上述问题，可用于烯烃氢甲酰化反应中。
• 1,8-Dimethylnaphthalene-bridged diphosphine ligands: synthesis and structural comparison of their palladium complexes
  作者：Ronan M. Bellabarba、Colin Hammond、Grant S. Forman、Robert P. Tooze、Alexandra M. Z. Slawin

  DOI：10.1039/b600837b

  日期：——

  affected by not only ligand demands, but also by the palladium oxidation state and the electronic properties of the ligands. Two qualitative stability series are also identified: 9 < 10 < 11 approximately 12 is observed, and P2Pd(dba) complexes are more stable than the corresponding P2PdCl2 complexes towards opening of the chelate ring. It is also concluded that the bite angle is heavily influenced

  报道了具有1,8-二甲基萘骨架的一系列新的配体的合成1,8-（R2PCH2）2C10H6，其中R =（t）Bu 1（dbpn），（i）Pr 2（dippn），Cy 3（dchpn）和Ph 4（dphpn）。配体1在结构上通过X射线晶体学表征。比较了复合物6、7、8、10、11和12的X射线晶体结构，对（diphosphine）Pd（dba）和（diphosphine）PdCl2复合物进行了比较结构研究。金属的几何形状不仅受配体需求的影响，而且还受钯的氧化态和配体的电子性能的影响。还确定了两个定性稳定性序列：观察到9 <10 <11约12，并且P2Pd（dba）配合物比相应的P2PdCl2配合物在螯合环打开时更稳定。
• Preparation and characterization of palladium and platinum complexes bearing 1,8-bis[(diphenylphosphino)methyl]naphthalene
  作者：Yasuhiro Yamamoto、Yasushi Fukui、Katsuaki Matsubara、Hiroya Takeshima、Fumiyoshi Miyauchi、Tomoaki Tanase、Gaku Yamamoto

  DOI：10.1039/b100860i

  日期：——

  Reaction of MCl2(cod) (M = Pd, Pt) with 1,8-bis[(diphenylphosphino)methyl]naphthalene (1,8-dpmn) gave MCl2(1,8-dpmn) 1 (M = Pd), 2 (M = Pt), as confirmed by X-ray analyses. Complex 1 reacted with xylyl isocyanide a (XylNC) in the presence of NaPF6 to give [Pd(1,8-dpmn)(XylNC)2](PF6)23a. Reactions of dinuclear complexes [M2(RNC)6](PF6)2 (4: M = Pd, 5: M = Pt; R = Xyl (a) or 2,4,6-Me3C6H2 (b) (Mes)) with one or two equiv. of 1,8-dpmn gave [M2(1,8-dpmn)(RNC)4](PF6)26 (M = Pd) and 7 (M = Pt), or [M2(1,8-dpmn)2(RNC)2](PF6)28 (M = Pd) and 9 (M = Pt). The structures of 6b, 7b and 8b were confirmed by X-ray analyses. Reaction of [Pd2Cl2(XylNC)4] with two equiv. of 1,8-dpmn in the presence of NaPF6 gave 8a, whereas the reaction in the presence of NH4PF6 produced 10a together with 7a. It was confirmed by an X-ray analysis of 10a that the crystal lattice is constructed by two types of cations (3a and two 2,2,6,6-tetramethyl-4-piperidonium) and four PF6 anions. Photochemical reaction of 6a or 8a in CH2Cl2 led to cleavage of the Pd–Pd bond, giving [PdCl(XylNC)3](PF6) and [PdCl(1,8-dpmn)(XylNC)](PF6).

  MCl2(cod) (M = Pd, Pt) 与 1,8-双[(二苯基膦)甲基]萘 (1,8-dpmn) 反应，得到 MCl2(1,8-dpmn) 1 (M = Pd), 2 (M = Pt)，X 射线分析证实了这一点。络合物 1 在 NaPF6 存在下与二甲苯基异氰酸酯 a (XylNC) 反应，得到 [Pd(1,8-dpmn)(XylNC)2](PF6)23a。双核配合物 [M2(RNC)6](PF6)2（4：M = Pd，5：M = Pt；R = Xyl (a) 或 2,4,6-Me3C6H2 (b) (Mes)）与 1 或 2 个等当量的 1,8-dpmn 反应，得到 [Pd(1,8-dpmn)(XylNC)2](PF6)23a。1,8-dpmn，得到 [M2(1,8-dpmn)(RNC)4](PF6)26（M = Pd）和 7（M = Pt），或 [M2(1,8-dpmn)2(RNC)2](PF6)28（M = Pd）和 9（M = Pt）。X射线分析证实了6b、7b和8b的结构。在 NaPF6 存在下，[Pd2Cl2(XylNC)4] 与两当量的 1,8-dpmn 反应生成 8a，而在 NH4PF6 存在下反应生成 10a 和 7a。通过对 10a 的 X 射线分析证实，其晶格是由两种阳离子（3a 和两个 2,2,6,6-四甲基-4-哌啶鎓）和四个 PF6 阴离子构成的。6a 或 8a 在 CH2Cl2 中发生光化学反应，导致 Pd-Pd 键断裂，生成 [PdCl(XylNC)3](PF6)和 [PdCl(1,8-dpmn)(XylNC)](PF6)。
• Syntheses and crystal structures of binuclear ruthenium complexes bearing 1,8′-bis(diphenylphosphinomethyl)naphthalene
  作者：Chang-Bin Yu、Yu-Qing Xia、Xiao-Hong Tian、Xiang-Ge Zhou、Guang-Ying Fan、Rui-Xiang Li、Xian-Jun Li、Kim-Chung Tin、Ning-Bew Wong

  DOI：10.1016/j.jorganchem.2005.04.061

  日期：2006.1

  Treatment of [RuCl2(η6-C6H6)]x with bidentate phosphine ligand BDNA [1,8-bis(diphenylphosphinomethyl)naphthalene] in methanol at room temperature gave η6-benzene-ruthenium complexes Ru2Cl4(η6-C6H6)2(μ-BDNA) (1). Complex 1 further reacted with AgBF4 to form complex [Ru2Cl2(μ-Cl)(η6-C6H6)2(μ-BDNA)](BF4) (2). [RuCl2(η6-C6H6)]x reacted with BDNA in refluxing methanol and then the reaction solution was

  的治疗将[RuCl 2（η 6 -C 6 H ^ 6）] X与在室温下的二齿膦配位体BDNA [1,8-二（二苯基膦基）萘]在甲醇，得到η 6 -苯钌络合物的Ru 2氯4（ η 6 -C 6 H ^ 6）2（μ-BDNA）（1）。复杂1与的AgBF进一步反应4以形成复杂的[Ru 2氯2（μ-Cl）的（η 6 -C 6 H ^ 6）2（μ-BDNA）]（BF4）（2）。将[RuCl 2（η 6 -C 6 H ^ 6）] X在回流的甲醇中用BDNA反应，然后将反应溶液用的AgBF处理4，以生成复杂的[Ru 2氯2（η 6 -C 6 H ^ 6）2（μ -BDNA）2 ]（BF 4）2（3）。它们的组成和结构已通过元素分析，NMR光谱和单晶X射线衍射确定。X射线衍射表明配合物1属于单斜晶体系统，P 2 1 / c空间群，Z  = 4，a  = 12.810Å，b  = 21.507Å，c  = 18
• Novel aldehydes and process for producing the same
  申请人：TOA NENRYO KOGYO KABUSHIKI KAISHA

  公开号：EP0083158A1

  公开（公告）日：1983-07-06

  A novel aldehyde, 4-formylcyclohexane-1,2-dicarboxylic acid, is prepared by the reaction of 4-cyclohexene-1,2-dicarboxylic acid with hydrogen and carbon monoxide in the presence of a hydroformylation catalyst. Products in which hydrogen of the ring is substituted by other groups, and derivatives of the carboxyl groups, may also be prepared. Useful catalysts include rhodium carbonyl complex compounds with tertiary phosphine ligands with excess of the tertiary phosphine ligands.

  4- 甲酰基环己烯-1,2-二羧酸是由 4-环己烯-1,2-二羧酸与氢气和一氧化碳在加氢甲酰化催化剂存在下反应制备而成。也可以制备环中氢被其他基团取代的产品以及羧基的衍生物。有用的催化剂包括含有过量叔膦配体的铑羰基络合物。