(SP-4-1)-bis(acetone oxime-κN)dichloridoplatinum(II) | 15022-74-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (SP-4-1)-bis(acetone oxime-κN)dichloridoplatinum(II)
• 英文别名: trans-[PtCl2(2-propanone oxime)2]；{Pt<(axH)2>Cl2}；trans-[PtCl2((CH3)2C=NOH)2]；trans-(PtCl2(HON=CMe2)2)；trans-PtCl2(Me2CNOH)2；trans-[PtCl2(acetoneoxime)2]；platinum(2+);N-propan-2-ylidenehydroxylamine;dichloride
• CAS: 15022-74-9；15022-73-8
• 化学式: C₆H₁₄Cl₂N₂O₂Pt
• 分子量: 412.175
• InChiKey: JKNDHWNOMRXYSH-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -4.28
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (SP-4-1)-bis(acetone oxime-κN)dichloridoplatinum(II) 在 AgNO₃ 、 NaOH 作用下， 以 硝基甲烷 、 水 为溶剂， 生成 [Pt(2-propanone oximate)2(2-propanone oxime)2]
  参考文献：
  名称：

  Hydrogen-Bonding Patterns in Oxime/Oximato Platinum(II) Species Providing the Formation of One-Dimensional Chains, Two-Dimensional Networks, and Cages

  摘要：

  Heating cis-[PtCl2(Me2C=OH)(2)] in molten 2-propanone oxime affords the cationic complex [PtCl(Me2C=NOH)(3)]Cl. This compound reacts with 1 equiv of NaOH to give the neutral complex cis-[PtCl(Me2C=NO)(Me2C=NOH)(2)] (1). Further, the reaction of [PtCl(Me2C=NOH)(3)]Cl with 2 equiv of AgNO3 and successive addition of excess oxime and NaSbF6 afford the chloride-free cationic complex [Pt(Me2C=NO)(Me2C=NOH)3](SbF6). When a solution of NaOH, instead of NaSbF6, was added to the reaction mixture, the neutral compound [Pt(Me2C=NO)(2)(Me2C=NOH)(2)] . 2H(2)O (2) was isolated. The homoleptic complex [Pt(Me2C=NOH)(4)]Cl-2 (3) was prepared both by addition of excess HCl to [Pt(Me2C=NO)(2)(Me2C=NOH)(2)] (87% yield) and by prolonged heating of [PtCl(Me2C=NOH)(3)]Cl and excess 2-propanone oxime, although in the latter case the conversion of the starting complex did not exceed 5-10%. 1-3 were characterized by X-ray diffraction. All three compounds display interesting hydrogen-bonding modes. In 1, two crystallographically independent molecules of cis-[PtCl(Me2C=NO)(Me2C=NOH)(2)] form, the repeat unit for a novel type of self-assembly that produces infinite one-dimensional polymeric chains held by strong H-bonds. 2, as compared to vic-dioxime Pt(II) complexes, displays stronger intramolecular hydrogen bonds and shows the absence of columnar stacking. In addition, the solvation H2O molecules connect the Pt(n) building elements by intermolecular H-bonds to form a layered two-dimensional network. In 3, the counterion is involved in (mu(4)-Cl-).cis-[(... H-O-)(2)(... H-CH2-)(2)] hydrogen bonding, thus forming the caged complex. Another interesting structural feature of 3 is the interaction between methyl hydrogens and platinum.

  DOI：

  10.1021/ic970501u
• 作为产物：
  描述：

  [Pt(2-propanone oximate)2(2-propanone oxime)2] 以 水 为溶剂， 生成 (SP-4-1)-bis(acetone oxime-κN)dichloridoplatinum(II)
  参考文献：
  名称：

  Hydrogen-Bonding Patterns in Oxime/Oximato Platinum(II) Species Providing the Formation of One-Dimensional Chains, Two-Dimensional Networks, and Cages

  摘要：

  Heating cis-[PtCl2(Me2C=OH)(2)] in molten 2-propanone oxime affords the cationic complex [PtCl(Me2C=NOH)(3)]Cl. This compound reacts with 1 equiv of NaOH to give the neutral complex cis-[PtCl(Me2C=NO)(Me2C=NOH)(2)] (1). Further, the reaction of [PtCl(Me2C=NOH)(3)]Cl with 2 equiv of AgNO3 and successive addition of excess oxime and NaSbF6 afford the chloride-free cationic complex [Pt(Me2C=NO)(Me2C=NOH)3](SbF6). When a solution of NaOH, instead of NaSbF6, was added to the reaction mixture, the neutral compound [Pt(Me2C=NO)(2)(Me2C=NOH)(2)] . 2H(2)O (2) was isolated. The homoleptic complex [Pt(Me2C=NOH)(4)]Cl-2 (3) was prepared both by addition of excess HCl to [Pt(Me2C=NO)(2)(Me2C=NOH)(2)] (87% yield) and by prolonged heating of [PtCl(Me2C=NOH)(3)]Cl and excess 2-propanone oxime, although in the latter case the conversion of the starting complex did not exceed 5-10%. 1-3 were characterized by X-ray diffraction. All three compounds display interesting hydrogen-bonding modes. In 1, two crystallographically independent molecules of cis-[PtCl(Me2C=NO)(Me2C=NOH)(2)] form, the repeat unit for a novel type of self-assembly that produces infinite one-dimensional polymeric chains held by strong H-bonds. 2, as compared to vic-dioxime Pt(II) complexes, displays stronger intramolecular hydrogen bonds and shows the absence of columnar stacking. In addition, the solvation H2O molecules connect the Pt(n) building elements by intermolecular H-bonds to form a layered two-dimensional network. In 3, the counterion is involved in (mu(4)-Cl-).cis-[(... H-O-)(2)(... H-CH2-)(2)] hydrogen bonding, thus forming the caged complex. Another interesting structural feature of 3 is the interaction between methyl hydrogens and platinum.

  DOI：

  10.1021/ic970501u

文献信息

• Novel Oximato-Bridged Platinum(II) Di- and Trimer(s): Synthetic, Structural, and in Vitro Anticancer Activity Studies
  作者：Yulia Yu. Scaffidi-Domianello、Anton A. Legin、Michael A. Jakupec、Alexander Roller、Vadim Yu. Kukushkin、Mathea Sophia Galanski、Bernhard K. Keppler

  DOI：10.1021/ic300148e

  日期：2012.7.2

  spectrometry, IR and multinuclear (1H, 13C, and 195Pt) NMR spectroscopy, as well as X-ray diffraction in the cases of dimers 6 and 9. Furthermore, the crystal and molecular structures of a trimeric oximato-bridged complex 11 comprising three platinum units connected in a chain way were established. The cytotoxicity of both dimers and the respective monomers was comparatively evaluated in three human cancer

  新型反式铂配合物 [PtCl 2 ( Z )-R(H)C=NOH} 2 ] [R = Me ( 1 ), Et ( 3 )] 和 [PtCl 2 ( E )-R(H) C═NOH}( Z )-R(H)C═NOH}] [R = Me ( 2 ), Et ( 4 )] 以及经典反式-[PtCl 2 (R 2 C=NOH) 2 ] [R = Me, Et] 在环境温度下与丙酮溶液中等量的醋酸银反应，形成前所未有的头对尾定向肟基桥联二聚体 [PtClμ-( Z )-R( H)C=NO}( Z)-R(H)C=NOH}] 2 [R = Me ( 5 ), Et ( 7 )], [PtClμ-( Z )-R(H)C=NO}( E )-R( H)C=NOH}] 2 [R = Me ( 6 ), Et ( 8 )] 和 [PtCl(μ-R 2 C= NO)(R 2 C= NOH)] 2 [R =
• An efficient method for selective oxidation of (oxime)Pt(II) to (oxime)Pt(IV) species using N,N-dichlorotosylamide
  作者：Anastasiia M. Afanasenko、Evgeny Yu. Bulatov、Tatiana G. Chulkova、Matti Haukka、Fedor M. Dolgushin

  DOI：10.1007/s11243-016-0034-7

  日期：2016.5

  The oxidation of (oxime)PtII species using the electrophilic chlorine-based oxidant N,N-dichlorotosylamide (4-CH3C6H4SO2NCl2) was studied. The reactions of trans-[PtCl2(oxime)2] (where oxime = acetoxime, cyclopentanone oxime, or acetaldoxime) with this oxidant led to trans-[PtCl4(oxime)2] products. The oxidation of trans-[Pt(o-OC6H4CH = NOH)2] at room temperature gave trans-[PtCl2(o-OC6H4CH = NOH)2]

  研究了使用亲电子氯基氧化剂 N,N-二氯甲苯磺酰胺 (4-CH3C6H4SO2NCl2) 氧化（肟）PtII 物质。反式-[PtCl2(肟)2]（其中肟=乙酰肟、环戊酮肟或乙醛肟）与该氧化剂的反应产生反式-[PtCl4(肟)2]产物。反式-[Pt(o-OC6H4CH = NOH)2] 在室温下氧化得到反式-[PtCl2(o-OC6H4CH = NOH)2]，而加热时的相同反应伴随着苯环的亲电取代。
• Reactivity of <i>trans</i>-[PtX₂(ketoxime)₂] Complexes toward <i>m</i>-Chloroperoxybenzoic Acid:  An Efficient Route to Coordinated Nitrosoalkanes and Solvent Dependence of the Reaction
  作者：Vadim Yu. Kukushkin、David Tudela、Youlia A. Izotova、Vitaly K. Belsky、Adam I. Stash

  DOI：10.1021/ic9600691

  日期：1996.1.1

  The platinum(II) compounds trans-[PtX(2)(RR'C=NOH)(2)] [X = Cl, R = R' = Me, RR' = (CH(2))(4), (CH(2))(5); X = Br, R = R' = Me] react with m-chloroperoxybenzoic acid (MCPBA) in dimethylformamide to give the platinum(II) complexes [PtX(2)N(=O)CRR'ONCRR'}] containing coordinated nitrosoalkane ligands. The complexes [PtX(2)N(=O)CRR'ONCRR'}] were characterized by elemental analysis, EI-MS, IR, electronic

  铂（II）化合物反式-[PtX（2）（RR'C = NOH）（2）] [X = Cl，R = R'= Me，RR'=（CH（2））（4），（ CH（2））（5）；X = Br，R = R'= Me]与二甲基甲酰胺中的间氯过氧苯甲酸（MCPBA）反应，得到含有配位亚硝基链烷的铂（II）配合物[PtX（2）N（= O）CRR'ONCRR'}]配体。配合物[PtX（2）N（= O）CRR'ONCRR'}]通过元素分析，EI-MS，IR，电子吸收和（1）H NMR光谱表征。对[PtCl（2）N（= O）CC（5）H（10）ONCC（5）H（10）}]进行了X射线结构分析。后者的化合物以三斜晶P＆onemacr结晶。a = 9.214（2）Å，b = 9.577（2）Å，c = 10.367（2）Å，alpha = 109.14（2）度，beta = 91.87（2）度，gamma = 115
• Unusual Reactivity Mode of Coordinated Oximes:  Platinum(IV)-Assisted Ring Closure by Reaction with Acetone
  作者：Vadim Yu. Kukushkin、Vitaly K. Belsky、David Tudela

  DOI：10.1021/ic950351s

  日期：1996.1.1

  The platinum(II) complexes trans-[PtCl(2)(RR'C=NOH)(2)], where R = R' = Me, RR' = (CH(2))(4) and (CH(2))(5), react with m-chloroperoxybenzoic acid in Me(2)CO to give the platinum(IV) complexes [PtCl(2)(OCMe(2)ON=CRR')(2)] in 50-60% yields. The complexes [PtCl(2)(OCMe(2)ON=CRR')(2)] were characterized by elemental analysis, EI-MS, and IR and Raman spectroscopies; X-ray structure analyses were performed

  铂（II）配合物反式-[PtCl（2）（RR'C = NOH）（2）]，其中R = R'= Me，RR'=（CH（2））（4）和（CH（2 ））（5），与间氯过氧苯甲酸在Me（2）CO中反应，得到50-60％的铂（IV）络合物[PtCl（2）（OCMe（2）ON = CRR'）（2）]产量。配合物[PtCl（2）（OCMe（2）ON = CRR'）（2）]通过元素分析，EI-MS，红外光谱和拉曼光谱法表征。反-[PtCl（2）（OCMe（2）ON = CC（4）H（8））（2）]和反-[PtCl（2）（OCMe（2）ON）的X射线结构分析= CC（5）H（10））（2）]。前一种化合物在三斜空间群P＆onemacr;中结晶。其中a = 8.088（2）Å，b = 8.327（2）Å，c = 8.475（2）Å，alpha = 103.54（3）度，beta = 102.15（3）度，gamma
• Reduction of (imine)Pt(IV) to (imine)Pt(II) Complexes with Carbonyl-Stabilized Phosphorus Ylides
  作者：Gabriele Wagner、Tatyana B. Pakhomova、Nadezhda A. Bokach、João J. R. Fraústo da Silva、Jose Vicente、Armando J. L. Pombeiro、Vadim Yu. Kukushkin

  DOI：10.1021/ic000769c

  日期：2001.3.1

  other Pt(II)/Pt(IV) couples, and the ylides Ph3P=CHCO2R are introduced as mild and selective reducing agents of wide applicability for the conversion of Pt(IV) to Pt(II) species in nonaqueous media, a route that is especially useful in the case of compounds that cannot be prepared directly from Pt(II) precursors, and for the generation of systematic series of Pt(II)/Pt(IV) complexes for biological studies

  报道了一种难以获得的（亚胺）Pt（II）化合物的新方法，该方法涉及通过羰基稳定的磷化磷（Ph3P = CHCO2R）在非水中还原相应的基于Pt（IV）的亚胺。媒体。中性（亚氨基）Pt（IV）化合物[PtCl4 [NH = C（Me）ON = CR1R2] 2]之间的反应[R1R2 = Me2，（CH2）4，（CH2）5，（Me）C（Me）= NOH]，[PtCl4 [NH = C（Me）ONR2] 2]（R = Me，Et，CH2Ph），（R1 = H; R2 = Ph或C6H4Me; R3 = Me）以及阴离子型铂（IV ）配合物（Ph3PCH2Ph）[PtCl5 [NH = C（Me）ON = CR2]] [R2 = Me2，（CH2）4，（CH2）5]和1当量的Ph3P = CHCO2R（R = Me，Et）在在温和的条件下（约4小时，室温）选择性地得到铂（II）产物（具有优良的分离