N,N'-bis(diphenylmethylene)-1,3-propanediamine | 1093215-24-7

• 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,N'-bis(diphenylmethylene)-1,3-propanediamine
• 英文别名: N-[3-(benzhydrylideneamino)propyl]-1,1-diphenylmethanimine
• CAS: 1093215-24-7
• 化学式: C₂₉H₂₆N₂
• 分子量: 402.539
• InChiKey: VVDDYADKEAHVJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N'-bis(diphenylmethylene)-1,3-propanediamine 在 copper(II) choride dihydrate 作用下， 以 四氢呋喃 为溶剂， 生成 二苯甲酮
  参考文献：
  名称：

  An investigation of Cu(II) and Ni(II)-catalysed hydrolysis of (di)imines

  摘要：

  The reactions of six diimine ligands with Cu(II) and Ni(II) halide salts have been investigated. The diimine ligands were Ph(2)C=N(CH(2))(n)NC=Ph(2) (n = 2 (Bz(2)en, 1a), 3 (Bz(2)pn, 1b), 4 (Bz2bn, 1c)), N, N'-bis-(2-tert-butylthio- 1-ylmethylenebenzene)-2,2'diamino-biphenyl (2), N,N'-bis-(2-chloro-1-ylmethylenebenzene)-1,3diaminobenzene (3) and N,N'-bis-(2-chloro-1-ylmethylenebenzene)-1,2-ethanediamine (4). Reactions of 1a-c, 2-4 with CuCl(2)center dot 2H(2)O in dry ethanol at ambient temperature led to complete or partial hydrolysis of the diimine ligands to ultimately form copper diamine complexes. The non-hydrolyzed complexes of 1b and 1c, [Cu(L)Cl(2)] (L = 1b, 1c), could be isolated when the reactions were carried out at low temperatures, and the half-hydrolyzed complex [Cu(Bzpn)Cl(2)] could also be identified via X-ray crystallography. Similarly, reactions of 1a or 1b with NiCl(2)center dot 6H(2)O or [NiBr(2)(dme)] led to rapid hydrolysis of the imines and Ni complexes containing half-hydrolyzed 1a (Bzen; [trans-[Ni(Bzen)(2)Br(2)]) and 1b (Bzpn; [Ni(Bzpn) Br(2)] could be isolated and identified via single crystal X-ray analysis. Kinetic studies were made of the hydrolyses of 1a, 1b in THF and 2 in acetone, in the presence of Cu(II), and of 1a in acetonitrile, in the presence of Ni(II). Activation parameters were determined for the latter reaction and for the copper-catalyzed hydrolysis of 2; the relatively large negative activation entropies clearly indicate rate-determining steps of an associative nature. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.05.025
• 作为产物：
  描述：

  二苯甲酮 、 1,3-丙二胺 在 高氯酸 作用下， 以 甲醇 为溶剂， 以65 %的产率得到N,N'-bis(diphenylmethylene)-1,3-propanediamine
  参考文献：
  名称：

  非环状二氮杂配体及其金属配合物：合成、表征和生物学研究

  摘要：

  涉及各种酮和胺的缩合反应形成非环状配体，表示为LI、LII、LIII和LIV。乙二胺与苯乙酮、苯甲酰丙酮（在 70% HClO4 存在下）和二苯甲酮反应，生成以下非环状配体：(E,E)-N,N-双(1-苯基亚乙基)乙二胺 (LI)、双分别为(1-3-羟基-3-苯基丁-2-烯-亚基)(LII)和(E,E)-N,N-双(1,1-二苯基亚甲基)乙二胺(LIII)。二苯甲酮与 1,3-二氨基丙烷在甲醇溶液中以 1:1 的比例反应也合成了非环状配体 (E,E)-N,N-双(1,1-二苯基亚甲基)丙二胺 (利夫）。除 LII 外，所有合成的非环状配体在络合过程中都会分解，恢复为最初的酮和胺。相比之下，LII 表现出显着的稳定性，可以与 Ni(II)、Cu(II) 和 Co(II) 盐形成方形平面络合物。此外，当 Co(II) 络合物与 KNCS 反应时，可以转化为六配位 Co(III) 络合物 [Co

  DOI：

  10.14233/ajchem.2023.30567

文献信息

• Electron-Deficient Iron Alkyl Complexes Supported by Diimine Ligand (Ph₂CN)₂C₂H₄: Evidence for Reversible Ethylene Binding
  作者：Jeroen Volbeda、Auke Meetsma、Marco W. Bouwkamp

  DOI：10.1021/om8006773

  日期：2009.1.12

  Compound 5a decomposes at room temperature in bromobenzene-d5 or toluene-d8, affording dication [(Ph2CN)2C2H4}2Fe]2+ (6a); at elevated temperatures in toluene-d8 the formation of [(Ph2CN)2C2H4}Fe(CH2SiMe3)C6F5] (7a) was observed as well. Neither ferrous chloride (Ph2CN)2C2H4}FeCl2 activated with methylaluminoxane nor contact ion-pair 5a is active in the polymerization of ethylene. Instead we were able

  二亚胺配体（Ph 2 CN）2 C n H 2 n（n = 2，a ; n = 3，b）与FeCl 2或FeBr 2的反应导致形成相应的高自旋亚铁络合物（Ph 2 CN ）2 C 2 H 4 } FeX 2（1a，X = Cl; 2a，X = Br）和（Ph 2 CN）2 C 3 H 6 } FeCl 2（1b）。通过用二亚胺配体a处理（py）2 Fe（CH 2 SiMe 3）2来制备二烷基（Ph 2 CN）2 C 2 H 4 } Fe（CH 2 SiMe 3）2（3a）。在-30°C下将B（C 6 F 5）3添加到3a导致Me 3 SiCH 2提取，从而提供[（Ph 2 CN）2 C 2 H 4 } Fe（CH 2 SiMe3）] [Me 3 SiCH 2 B（C 6 F 5）3 ]（5a）。19 F NMR光谱显示该化合物以接触离子对形式存在于甲苯溶液中。化合物5a在室温下在溴苯-d
• Substituierte aliphatische Sekundäramine und ihre Salze, diese enthaltende pharmazeutische Präparate und ihre Verwendung
  申请人：CIBA-GEIGY AG

  公开号：EP0058373A1

  公开（公告）日：1982-08-25

  Verbindungen der Formel 1 worin R1 unsubstituiertes oder substituiertes Phenyl bedeutet, R2 Wasserstoff, Niederalkyl, unsubstituiertes oder substituiertes Phenyl oder freies oder verestertes Carboxy darstellt, und worin R3 Wasserstoff oder Niederalkyl und R4 eine Gruppe der Formel -alk1-X-alk2-R5 bedeutet oder R3 und R4 gemeinsam eine Gruppe der Formel -alk3-NH-alk4-darstellen, wobei alk, und alk2 Niederalkyliden bedeuten, alk3 und alk4 für Niederalkylen stehen, X eine direkte Bindung, Methylen oder unsubstituiertes oder substituiertes Phenylen darstellt, R5 Hydroxy, Amino oder substituiertes Amino der Formel -N(R6)-CH(R7)-R8 bedeutet, in der R6 für Wasserstoff steht oder, sofern R3 Wasserstoff ist, auch Niederalkyl oder unsubstituiertes oder substituiertes Phenylniederalkyl bedeuten kann, R7 Wasserstoff, Niederalkyl, unsubstituiertes oder substituiertes Phenyl oder freies oder verestertes Carboxy darstellt und R8 unsubstituiertes oder substituiertes Phenyl bedeutet, und ihre pharmazeutisch verwendbaren Salze haben atmungserleichternde Eigenschaften und eignen sich zur Bekämpfung von Atmungsstörungen, vorzugsweise als Wirkstoff in und/oder zur Herstellung von atmungserleichternden pharmazeutischen Präparaten.

  式 1 的化合物 其中 R1 是未取代或取代的苯基，R2 是氢、低级烷基、未取代或取代的苯基或游离或酯化的羧基，R3 是氢或低级烷基，R4 是式 -alk1-X-alk2-R5 的基团，或 R3 和 R4 共同代表式 -alk3-NH-alk4- 的基团、其中alk和alk2为亚低级烷基，alk3和alk4为亚低级亚烷基，X为直接键、亚甲基或未取代或取代的亚苯基，R5为羟基、式-N(R6)-CH(R7)-R8的氨基或取代的氨基、其中 R6 是氢，或者如果 R3 是氢，也可以是低级烷基或未取代或取代的苯基-低级烷基，R7 是氢、低级烷基、未取代或取代的苯基或游离或酯化的羧基，R8 是未取代或取代的苯基，它们的药用盐具有促进呼吸的特性，适用于防治呼吸系统疾病，最好作为促进呼吸药物组合物中和/或制备促进呼吸药物组合物的活性成分。
• Unconjugated diimine palladium complexes as Heck coupling catalysts
  作者：Simphiwe M. Nelana、Jezreel Cloete、George C. Lisensky、Ebbe Nordlander、Ilia A. Guzei、Selwyn F. Mapolie、James Darkwa

  DOI：10.1016/j.molcata.2008.01.009

  日期：2008.4

  Four unconjugated diimine palladium complexes have been synthesized, and spectroscopically and structurally characterized. All four palladium complexes were used as catalysts in the Heck coupling reaction between iodobenzene and methyl acrylate or butyl acrylate with very good conversion to either methyl (2E)-3-phenylacrylate or butyl (2E)-3-phenylacrylate. (c) 2008 Elsevier B.V. All rights reserved.
• US4448776A
  申请人：——

  公开号：US4448776A

  公开（公告）日：1984-05-15
• An investigation of Cu(II) and Ni(II)-catalysed hydrolysis of (di)imines
  作者：Miklós Czaun、Simphiwe M. Nelana、Ilia A. Guzei、Catrin Hasselgren、Mikael Håkansson、Susan Jagner、George Lisensky、James Darkwa、Ebbe Nordlander

  DOI：10.1016/j.ica.2010.05.025

  日期：2010.10

  The reactions of six diimine ligands with Cu(II) and Ni(II) halide salts have been investigated. The diimine ligands were Ph(2)C=N(CH(2))(n)NC=Ph(2) (n = 2 (Bz(2)en, 1a), 3 (Bz(2)pn, 1b), 4 (Bz2bn, 1c)), N, N'-bis-(2-tert-butylthio- 1-ylmethylenebenzene)-2,2'diamino-biphenyl (2), N,N'-bis-(2-chloro-1-ylmethylenebenzene)-1,3diaminobenzene (3) and N,N'-bis-(2-chloro-1-ylmethylenebenzene)-1,2-ethanediamine (4). Reactions of 1a-c, 2-4 with CuCl(2)center dot 2H(2)O in dry ethanol at ambient temperature led to complete or partial hydrolysis of the diimine ligands to ultimately form copper diamine complexes. The non-hydrolyzed complexes of 1b and 1c, [Cu(L)Cl(2)] (L = 1b, 1c), could be isolated when the reactions were carried out at low temperatures, and the half-hydrolyzed complex [Cu(Bzpn)Cl(2)] could also be identified via X-ray crystallography. Similarly, reactions of 1a or 1b with NiCl(2)center dot 6H(2)O or [NiBr(2)(dme)] led to rapid hydrolysis of the imines and Ni complexes containing half-hydrolyzed 1a (Bzen; [trans-[Ni(Bzen)(2)Br(2)]) and 1b (Bzpn; [Ni(Bzpn) Br(2)] could be isolated and identified via single crystal X-ray analysis. Kinetic studies were made of the hydrolyses of 1a, 1b in THF and 2 in acetone, in the presence of Cu(II), and of 1a in acetonitrile, in the presence of Ni(II). Activation parameters were determined for the latter reaction and for the copper-catalyzed hydrolysis of 2; the relatively large negative activation entropies clearly indicate rate-determining steps of an associative nature. (C) 2010 Elsevier B.V. All rights reserved.