N-(2-(diphenylphosphino)benzylidene)(thiophen-2-yl)methanamine | 1338578-19-0

• 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: N-(2-(diphenylphosphino)benzylidene)(thiophen-2-yl)methanamine
• 英文别名: (2-diphenylphosphanyl-benzylidene)-thiophen-2-ylmethyl-amine；(2-diphenylphosphino-benzylidene)-thiophen-3-ylmethyl-amine；(2-diphenylphosphinobenzylidene)thiophen-2-ylmethylamine；1-(2-diphenylphosphanylphenyl)-N-(thiophen-2-ylmethyl)methanimine
• CAS: 1338578-19-0
• 化学式: C₂₄H₂₀NPS
• 分子量: 385.469
• InChiKey: VIACIICQOCMSKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  dichloro(cycloocta-1,5-diene)palladium (II) 、 N-(2-(diphenylphosphino)benzylidene)(thiophen-2-yl)methanamine 以 二氯甲烷 为溶剂， 反应 4.0h， 以65%的产率得到[PdCl((2-diphenylphosphino-benzylidene)-thiophen-3-ylmethyl-amine-N,P)]
  参考文献：
  名称：

  Synthesis, characterisation and in vitro evaluation of palladium(II) iminophosphine complexes for anticancer activity

  摘要：

  室温下，亚氨基膦配体（L1-L7）分别与[PdCl2(COD)]和[PdMeCl(COD)]在CH2Cl2中发生反应，得到了钯(II)配合物。利用元素分析、电喷雾电离质谱、核磁共振（1H 和 31P）、红外光谱和 X 射线衍射研究对这些钯（II）配合物进行了表征。络合物 2、7 和 8 的单晶 X 射线衍射分析表明，这些络合物呈现出略微扭曲的方形平面几何形状。体外细胞毒性研究结果表明，钯配合物具有中等活性，能阻断 WHCO1 细胞的增殖，其 IC50 范围为 19.02-45.27 μM，对 KYSE450 细胞株的 IC50 范围为 10.03-68.54 μM。

  DOI：

  10.1007/s11243-012-9674-4
• 作为产物：
  描述：

  2-噻吩甲胺 、 2-二苯基膦苯甲醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以92%的产率得到N-(2-(diphenylphosphino)benzylidene)(thiophen-2-yl)methanamine
  参考文献：
  名称：

  半不稳定的亚氨基膦钯（II）配合物：合成，分子结构和Heck反应中的评估。

  摘要：

  由2-（二苯基膦基）苯甲醛和噻吩胺制备了2-（二苯基膦基）苄基-（2-噻吩）甲基亚胺（V）和2-（二苯基膦基）苄基-（2-噻吩）乙基亚胺（VI）产量。V和VI与PdCl 2（cod）（cod =环辛二烯）或PdClMe（cod）等摩尔反应，得到钯（II）配合物I–IV。II的分子结构通过X射线晶体学确认。钯原子周围的配位几何在钯中心呈现出扭曲的方形平面几何形状。配合物I，II和IV被评估为在温和的反应条件下碘代苯与丙烯酸甲酯的Heck偶联反应的催化剂; 催化剂：0.1摩尔％，Et 3 N碱，MeCN，80℃回流8小时；用催化剂I（64％），II（68％）和IV（58％）在10 mmol规模上分离得到的产率。他们都表现出重大的活动。

  DOI：

  10.2478/s11696-013-0530-6

文献信息

• Synthesis and characterization of palladium(II) and platinum(II) metal complexes with iminophosphine ligands: X-ray crystal structures of platinum(II) complexes and use of palladium(II) complexes as pre-catalysts in Heck and Suzuki cross-coupling reactions
  作者：Haleden Chiririwa、Freeman Ntuli、Edison Muzenda、Alfred Muller

  DOI：10.1007/s11243-013-9703-y

  日期：2013.5

  spectrometry (ESI-MS) and elemental analysis. The representative solid-state molecular structures of the platinum complexes 1b and 2b were determined using single crystal X-ray diffraction analysis and revealed that the complexes exhibit a slightly distorted square-planar geometry. Furthermore, the palladium complexes were tested as potential catalysts in the Heck and Suzuki cross-coupling reactions.

  铂配合物 1b 和 2b 的代表性固态分子结构是使用单晶 X 射线衍射分析确定的，并显示配合物表现出轻微扭曲的方形平面几何形状。此外，钯配合物在 Heck 和 Suzuki 交叉偶联反应中作为潜在催化剂进行了测试。
• Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and application as Suzuki–Miyaura coupling catalysts
  作者：Tebello Mahamo、Mokgolela M. Mogorosi、John R. Moss、Selwyn F. Mapolie、J. Chris Slootweg、Koop Lammertsma、Gregory S. Smith

  DOI：10.1016/j.jorganchem.2011.12.021

  日期：2012.4

  Palladium(II) complexes of the general formulae [PdCl2(P∧N)] and [Pd(Me)Cl(P∧N)] were obtained from bidentate ligands bearing phosphine and imine donor groups. The complexes were shown to be highly active catalysts for the Suzuki–Miyaura cross-coupling reaction. The complexes are tolerant of a wide variety of reaction conditions such as solvent, choice of base as well as substituents on both arylboronic

  通式[PdCl 2（PPN）]和[Pd（Me）Cl（P∧N）]的钯（II）配合物是从带有膦和亚胺供体基团的双齿配体中获得的。该络合物被证明是铃木-宫浦交叉偶联反应的高活性催化剂。该配合物可耐受多种反应条件，例如溶剂，碱的选择以及芳基硼酸和芳基卤化物的替代物。
• Platinacycloalkane complexes containing [P,N] bidentate ligands: synthesis and decomposition studies
  作者：Tebello Mahamo、John R. Moss、Selwyn F. Mapolie、Gregory S. Smith、J. Chris Slootweg、Koop Lammertsma

  DOI：10.1039/c3dt52798k

  日期：——

  [Pt(N^P)(CH2)n] (n = 4, 6) were obtained by the reaction of [Pt(COD)(CH2)n] with the appropriate iminophosphine ligand (1a–1f). These complexes were characterised using a variety of spectroscopic and analytical techniques. X-ray structure analysis of complex 2a revealed a slightly distorted square planar geometry around platinum as a consequence of the ring strain imposed by the [P,N] chelate ring formed

  通过[Pt（COD）的反应获得了一系列新的类型为[Pt（N ^ P）（CH 2）n ]（n = 4，6）的铂环戊烷（2a–2f）和铂环庚烷（3a–3f）。）（CH 2）n ]与合适的亚氨基膦配体（1a-1f）。使用多种光谱和分析技术对这些配合物进行表征。配合物2a的X射线结构分析由于形成的[P，N]螯合环和金属环烷烃施加的环应变，结果表明铂周围的正方形平面几何形状略有变形。铂环戊烷的热分解分析表明，铂环戊烷非常稳定，分解反应需要高于100°C的温度才能发生。从热分解反应获得的主要产物是1-丁烯（对于铂环戊烷）和1-己烯（对于铂环庚烷）。
• Synthesis, characterisation and in vitro evaluation of palladium(II) iminophosphine complexes for anticancer activity
  作者：Haleden Chiririwa、John R. Moss、Denver Hendricks、Reinout Meijboom、Alfred Muller

  DOI：10.1007/s11243-012-9674-4

  日期：2013.3

  Palladium(II) complexes have been obtained from the reactions of the iminophosphine ligands, (L1–L7), respectively, with [PdCl2(COD)] and [PdMeCl(COD)] in CH2Cl2 at room temperature. The palladium(II) complexes were characterised using elemental analysis, electro spray ionisation–mass spectrometry (ESI–MS), NMR (1H and 31P), IR spectroscopy and X-ray diffraction studies. Single-crystal X-ray diffraction analysis for complexes 2, 7 and 8 revealed that the complexes exhibited a slightly distorted square planar geometry. In vitro cytotoxic study results show that the palladium complexes exhibit moderate activity and block the proliferation of WHCO1 cells with an IC50 range of 19.02–45.27 μM, and IC50 range of 10.03–68.54 μM for the KYSE450 cell lines.

  室温下，亚氨基膦配体（L1-L7）分别与[PdCl2(COD)]和[PdMeCl(COD)]在CH2Cl2中发生反应，得到了钯(II)配合物。利用元素分析、电喷雾电离质谱、核磁共振（1H 和 31P）、红外光谱和 X 射线衍射研究对这些钯（II）配合物进行了表征。络合物 2、7 和 8 的单晶 X 射线衍射分析表明，这些络合物呈现出略微扭曲的方形平面几何形状。体外细胞毒性研究结果表明，钯配合物具有中等活性，能阻断 WHCO1 细胞的增殖，其 IC50 范围为 19.02-45.27 μM，对 KYSE450 细胞株的 IC50 范围为 10.03-68.54 μM。
• Neutral palladium(II) complexes with P,N Schiff-base ligands: Synthesis, characterization and catalytic oligomerisation of ethylene
  作者：Mokgolela M. Mogorosi、Tebello Mahamo、John R. Moss、Selwyn F. Mapolie、J. Chris Slootweg、Koop Lammertsma、Gregory S. Smith

  DOI：10.1016/j.jorganchem.2011.07.042

  日期：2011.11

  New N-functionalised 2-phosphinobenzaldimino (P boolean AND N) ligands bearing 3-picolyl, furfuryl, thiophene-2-methyl, thiophene-2-ethyl, and benzyl groups have been prepared in good yield. The 2-phosphinobenzaldimino ligands were reacted with PdCl2(COD) to give the corresponding metal complexes of the type Pd(L)Cl-2 (L = 2-phosphinobenzaldimino (P boolean AND N) ligand). All compounds were fully characterized using spectroscopic and analytical techniques, including H-1, C-13, and P-31 NMR and IR spectroscopies, mass spectrometry and elemental analysis. Selected neutral palladium complexes were evaluated as catalyst precursors in ethylene oligomerisation reactions, after activation with a co-catalyst (MMAO, EtAlCl2, or Et2AlCl). (C) 2011 Elsevier B.V. All rights reserved.