1-(dinaphtho[2,1-d:1':2'-g][1,3,6,2]dioxathiaphosphocin-4-yl)-4-methylpiperazine | 916754-63-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(dinaphtho[2,1-d:1':2'-g][1,3,6,2]dioxathiaphosphocin-4-yl)-4-methylpiperazine
• 英文别名: 4-(dinaphtho[2,1-d:1',2'-g][1,3,6,2]dioxathiaphosphocin-4-yl)-4-methylpiperazine；1-(13,15-Dioxa-2-thia-14-phosphapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaen-14-yl)-4-methylpiperazine
• CAS: 916754-63-7
• 化学式: C₂₅H₂₃N₂O₂PS
• 分子量: 446.51
• InChiKey: PVLDAIIYXKJXRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  50.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(dinaphtho[2,1-d:1':2'-g][1,3,6,2]dioxathiaphosphocin-4-yl)-4-methylpiperazine 以 二氯甲烷 、 乙腈 为溶剂， 生成 [AuI(1-(dinaphtho[2,1-d:1',2'-g][1,3,6,2]dioxathiaphosphocin-4-yl)-4-methylpiperidine)]
  参考文献：
  名称：

  中环硫醚氨基亚膦酸酯的第 11 族金属配合物 [-OC10H6(μ-S)C10H6O-]PNC4H8E (E = O, NMe)

  摘要：

  中环硫醚氨基亚膦酸酯的第 11 族金属配合物 [-OC 10 H 6 (μ-S)C 10 H 6 O-]PNC 4 H 8 E {2a: E = O; 2b：E = NMe；IUPAC 名称：4-(dinaphtho[2,1-d:1',2'-g][1,3,6,2]dioxathiaphosphocin-4-yl)morpholine (2a), 1-(dinaphtho[2,1 -d:1',2'-g][1,3,6,2]dioxathiaphosphocin-4-yl)-4-methylpiperazine (2b)}。硫醚氨基亚膦酸酯 2a 和 2b 与 CuX（X = Cl、Br 和 I）以 1:1 的摩尔比反应，得到三配位的二聚复合物 [{[{-OC 10 H 6 (μ-S)C 10 H 6 O-}PNC 4 H 8 E-kP ]Cu(μ-X)} 2 ] (4a: E = O, X =

  DOI：

  10.1002/ejic.200600913

文献信息

• Synthesis of Neutral (Pd^II, Pt^II), Cationic (Pd^II), and Water-Induced Anionic (Pd^II) Complexes Containing New Mesocyclic Thioether−Aminophosphonite Ligands and Their Application in the Suzuki Cross-Coupling Reaction
  作者：Benudhar Punji、Joel T. Mague、Maravanji S. Balakrishna

  DOI：10.1021/ic061419e

  日期：2006.11.1

  Mesocyclic thioether-aminophosphonite ligands, -OC10H6(mu-S)C10H6O-}PNC4H8O(2a, 4-(dinaphtho[2,1-d:1', 2'-g][1,3,6,2]dioxathiaphosphocin-4-yl)morpholine) and -OC10H6(A-S)C10H6O-}PNC4H8NCH3 (2b, 1-(dinaphtho[2,1-d:1', 2'-g][1,3,6,2]dioxathiaphosphocin-4-yl)-4-methylpiperazine) are obtained by reacting -OC10H6(mu-S)C10H6O} PCl (1) with corresponding nucleophiles. The ligands 2a and 2b react with (PhCN)(2)PdCl2 or M(COD)Cl-2 (M = Pd-II or PtII) to afford P-coordinated cis-complexes, [(-OC10H6(mu-S)C10H6O-)PNC4H8X-kappa P}(2)MCl2] (3a, M = Pd-II, X) O; 3b, M = Pd-II, X = NMe; 4a, M = Pt-II, X = O; 4b, M = Pt-II, X = NMe). Compounds 2a and 2b, upon treatment with [Pd(eta(3)-C3H5)Cl](2) in the presence of AgOTf, produce the P,S-chelated cationic complexes, [(-OC10H6(mu-S)C10H6O-)PNC4H8X-kappa P, kappa S} Pd(eta(3)-C3H5)](CF3SO3) (5a, X) O and 5b, X = NMe). Treatment of 2a and 2b with ( PhCN) 2PdCl2 in the presence of trace amount of H2O affords P, S-chelated anionic complexes, [(-OC10H6(mu-S)C10H6O-)P(O)-kappa P, kappa S}PdCl2](H2NC4H8X) (6a, X = O and 6b, X = NMe), via P-N bond cleavage. The crystal structures of compounds 1, 2a, 2b, 4a, and 6a are reported. Compound 6a is a rare example of crystallographically characterized anionic transition metal complex containing a thioether-phosphonate ligand. Most of these palladium complexes proved to be very active catalysts for the Suzuki-Miyaura reaction with excellent turnover number (( TON), up to 9.2 x 10(4) using complex 6a as a catalyst).