1,3-bis(N,N,N',N'-tetramethylguanidino)propane | 289474-28-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1,3-bis(N,N,N',N'-tetramethylguanidino)propane
• 英文别名: bis(tetramethylguanidino)propane；btmgp；2,2-(propane-1,3-diyl)bis(1,1,3,3-tetramethylguanidine)；2',2'-(propane-1,3-diyl)bis(tetramethylguanidine)；N'',N'''''-1,3-propanediylbis[N,N,N',N'-tetramethyl-guanidine]；(Me2N)2CNCH2CH2CH2NC(NMe2)2；2-[3-[Bis(dimethylamino)methylideneamino]propyl]-1,1,3,3-tetramethylguanidine
• CAS: 289474-28-8
• 化学式: C₁₃H₃₀N₆
• 分子量: 270.421
• InChiKey: VOIBHDDPKWCLSC-UHFFFAOYSA-N

物化性质

• 沸点：
  426.8±15.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-bis(N,N,N',N'-tetramethylguanidino)propane 在 (C₅H₅)2Fe 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 [Cu(II)2(μ-hydroxo)2((Me2N)2CNCH2CH2CH2NC(NMe2)2)2](triflate)2
  参考文献：
  名称：

  Herres-Pawlis, Sonja; Verma, Pratik; Haase, Roxana, Journal of the American Chemical Society, 2009, vol. 131, p. 1154 - 1169

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 生成 1,3-bis(N,N,N',N'-tetramethylguanidino)propane
  参考文献：
  名称：

  Orthoamide 和 Iminiumsalze，IIC。Darstellung von N-(ω-氨基烷基)-N,N',N',N",N"-全烷基胍和N-(ω-氨基烷基)-N',N',N",N"-四甲基胍

  摘要：

  摘要 N,N,N',N'-四烷基氯甲脒氯化物 1a、b 与 ω-二甲氨基烷基胺 19、20 反应生成 N-(ω-二甲基氨基烷基)-胍盐 12、13 和 N-(ω-二甲基氨基烷基)-胍盐的混合物盐21、22。这些混合物在用氢氧化钠水溶液处理时转化为脲15、17和N-(ω-二甲氨基烷基)-胍23、25的混合物。N-(3-二甲基氨基丙基)-胍25a与硫酸二甲酯以1:1的摩尔比反应得到N-(3-二甲基氨基丙基)-N,N,N',N',N",N的混合物”-五甲基-胍盐29a和N-(3-二甲基氨丙基)-N,N',N',N”,N”-五甲基-胍-双(甲基硫酸盐)33a。硫酸二甲酯以2:1的摩尔比对胍23a、25a的作用提供双季盐32a、33a。烷基化试剂如碘甲烷，苄基溴、烯丙基溴和氯乙腈以 1:1 的摩尔比攻击 N-(2-二甲基氨基乙基)-N',N',N",N"-四乙基胍 (23b) 以 1:1 的摩尔比在二甲基氨基乙基基团上干净地攻击铵盐

  DOI：

  10.1515/znb-2019-0229

文献信息

• Systematische Studie zu den Koordinationseigenschaften des Guanidin-Liganden Bis(tetramethylguanidino)propan mit den Metallen Mangan, Cobalt, Nickel, Zink, Cadmium, Quecksilber und Silber. A Systematic Study on the Coordination Properties of the Guanidine
  作者：Adam Neuba、Sonja Herres-Pawlis、Oliver Seewald、Janna Börner、Andreas J. Heuwing、Ulrich Flörke、Gerald Henkel

  DOI：10.1002/zaac.201000133

  日期：2010.12

  straightforward formation of the mononuclear complexes 1–7 and the binuclear complex 8. In complexes with MII the metal ion shows a distorted tetrahedral coordination whereas in 8, the coordination of the MI ion is almost linear. The coordination behavior of btmgp and resulting structural parameters of the corresponding complexes were discussed in an comparative approach together with already described

  过渡金属与配体 1,3-双(N,N,N',N'-四甲基胍基)丙烷 (btmgp), [Mn(btmgp)Br2] (1), [Co(btmgp)Cl2] (2 ), [Ni(btmgp)I2] (3), [Zn(btmgp)Cl2] (4), [Zn(btmgp)(O2CCH3)2] (5), [Cd(btmgp)Cl2] (6), [首次制备并表征了 Hg(btmgp)Cl2] (7) 和 [Ag2(btmgp)2][ClO4]2·2MeCN (8)。相应的无水金属盐与配体 btmgp 在干燥的 MeCN 或 THF 中的化学计量反应导致单核配合物 1-7 和双核配合物 8 的直接形成。在与 MII 的配合物中，金属离子显示出扭曲的四面体配位而在 8 中，MI 离子的配位几乎是线性的。
• Tuning of Copper( <scp>I</scp> )–Dioxygen Reactivity by Bis(guanidine) Ligands
  作者：Sonja Herres‐Pawlis、Ulrich Flörke、Gerald Henkel

  DOI：10.1002/ejic.200400822

  日期：2005.10

  bis(tetramethylguanidino)-, bis(dipiperidinoguanidino)-, and bis(dimethylpropyleno)propane (btmgp, DPipG 2 p and DMPG 2 p, respectively), has been extended to include bis(dimethylethyleneguanidino)propane (DMEG 2 p), which has both N a m i n e atoms of each guanidine functionality connected by a short ethylene bridge, as a member. From this series, a family of novel bis(guanidine)copper(i) compounds - [Cu 2 (btmgp)

  设计用于仿生配位化学的一系列双（胍）配体，即双（四甲基胍基）-、双（二哌啶基胍基）-和双（二甲基丙烯基）丙烷（分别为 btmgp、DPipG 2 p 和 DMPG 2 p），具有已扩展到包括双（二甲基亚乙基胍基）丙烷（DMEG 2 p），它具有通过短亚乙基桥连接的每个胍官能团的两个 N 胺原子作为成员。来自该系列的一系列新型双（胍）铜 (i) 化合物 - [Cu 2 (btmgp) 2 ][PF 6 ] 2 (1), [Cu 2 (DPipC 2 p) 2 ](PF 6 ] 2 (2)、[Cu2(DMPG 2 p) 2 ][PF 6 ] 2 (3) 和[Cu 2 (DMEG 2 p) 2 ][PF 6 ] 2 .2MeCN (4) - 已经合成。1-4 的单晶 X 射线分析表明，这些化合物含有双核复合阳离子，这些阳离子含有十二元杂环 Cu 2 N 4 C 6 环，其中 Cu 原子相距超过 4
• 1,3-Bis(N,N,N′,N′-tetramethylguanidino)propane: synthesis, characterization and bonding properties of the first bidentate, peralkylated guanidine ligand †
  作者：Siegfried Pohl、Michael Harmjanz、Jörg Schneider、Wolfgang Saak、Gerald Henkel

  DOI：10.1039/b002554m

  日期：——

  The first bidentate, peralkylated guanidine based ligand has been synthesized and its complexation chemistry examined by the preparation of three representative coordination compounds. The novel chelate ligand 1,3-bis(N,N,N′,N′-tetramethylguanidino)propane (btmgp, 1) has been synthesized by the reaction of N,N,N′,N′tetramethylguanidine (TMG) with 1,3-dibromopropane and subsequent deprotonation of the resulting guanidinium salt with sodium ethoxide. The bifunctional N-donor compound was treated with copper(I) iodide, copper(II) chloride and iron(II) iodide in a 1∶1 molar ratio to yield the corresponding electroneutral complexes [CuI(btmgp)] 2, [CuCl2(btmgp)] 3 and [FeI2(btmgp)] 4. The structures of the dihydrochloride of 1 (1b) and of the complexes 2–4 have been determined by X-ray crystallography. A comparison of the molecular structures (2–4) shows that, in each case, btmgp acts as a bidentate ligand which is able to stabilize not only trigonal-planar (2), but also (distorted) square-planar (3) and tetrahedral coordination environments (4).

  通过制备三种具有代表性的配位化合物，合成了第一种双齿过烷基化胍基配体并研究了其络合化学性质。新型螯合配体 1,3-双（N,N,Nâ²,Nâ²-四甲基胍基）丙烷（btmgp, 1）是通过 N,N,Nâ²,Nâ²-四甲基胍 (TMG) 与 1,3-二溴丙烷反应并随后用乙醇钠对生成的胍盐进行去质子化而合成的。双官能 N-载体化合物与碘化铜（I）、氯化铜（II）和碘化铁（II）以 1¶1 的摩尔比进行处理，得到相应的电中性配合物 [CuI(btmgp)] 2、[CuCl2(btmgp) ] 3 和 [FeI2(btmgp)] 4。1 的二盐酸盐（1b）和复合物 2â4 的结构已通过 X 射线晶体学确定。分子结构（2â4）的比较表明，在每种情况下，btmgp 都是一种双齿配体，不仅能够稳定三方平面（2），还能稳定（扭曲的）方平面（3）和四面体配位环境（4）。
• New examples of μ-η2:η2-disulfido dicopper(II,II) complexes with bis(tetramethylguanidine) ligands
  作者：Urmila Pal Chaudhuri、Douglas R. Powell、Robert P. Houser

  DOI：10.1016/j.ica.2008.10.030

  日期：2009.5

  The new ligand N , N ′ - (2-methyl-2-(2-pyridyl)propan-1,3-diyl)bis(tetramethylguanidine) (L) and its four-coordinate, distorted square-planar copper(II) complex [CuLCl 2 ] ( 1 ) were synthesized and structurally characterized. Similarly, bis( μ -OH)dicopper(II,II) complex [Cu 2 L 2 (OH) 2 ](OTf) 2 ( 2 ) was synthesized and structurally characterized. The pyridyl group in L does not coordinate in either

  新的配体N，N'-（2-甲基-2-（2-吡啶基）丙烷-1,3-二基）双（四甲基胍）（L）及其四配位扭曲的方平面铜（II）配合物合成了[CuLCl 2]（1）并对其结构进行了表征。类似地，合成了双（μ-OH）二铜（II，II）配合物[Cu 2 L 2（OH）2]（OTf）2（2）。L中的吡啶基在1或2中均不配位。通过处理L或L'[L'= 2'，2'-（丙烷-1， 3-二基）双（1,1,3,3-四甲基胍）]与元素硫。[Cu 2 L 2（S 2）]（PF 6）2（3）和[Cu 2 L 2'（S 2）]（PF 6）2（4）均具有结构特征，并且两个结构均具有两个铜（ II）在μ-η2：η2-方式中由二硫键配体桥接的离子。配体L和L'以二齿形式配位（如1和2，吡啶环在3中不配位），并且在3和4中铜离子周围的几何形状扭曲为正方形平面。发现3和4的度量参数与其他μ-η2：η2-二硫键双铜（II，II）配合
• Syntheses and structures of transition metal thiolate complexes containing the new bis(tetramethylguanidine) ligand btmgp
  作者：Siegfried Pohl、Michael Harmjanz、Jörg Schneider、Wolfgang Saak、Gerald Henkel

  DOI：10.1016/s0020-1693(00)00310-8

  日期：2000.12

  Phe syntheses. spectroscopic and structural characterizations of the first iron and copper thiolate guanidine complexes are described. Reactions of the neutral complexes [Cu[(btmgp)] and [FeI2(btmgp)] [btmgp = 1,3-bis(N,N,N',N'-tetramethyl-guanidino)propane] with different uni- and bi-dentate thiolate ions yield the three-coordinate complex [Cu(S-2,4,6-(Bu3C6H2)-Bu-1)(btmgp)] (1) and the four-coordinate complexes [Fe(S-2,4,6-(Pr3C6H2)-Pr-1)(2)(btmgp)] (2) and [Fe(SiMe2(C6H4S)(2))(btmgp)] (3) respectively. Starting with [Fe(N(SiMe3)(2))(2)], btmgp and the dithiol SiMe2(C6H4SH)(2), an alternative procedure for the preparation of 3 is reported, demonstrating a useful synthetic approach towards neutral, N S mixed coordinated Fe(II) complexes. The X-ray structure analyses of 1 - 3 reveal trigonal planar (2N 1S) (1) and tetrahedral (2N 2S) (2, 3) coordination environments around the metal centers. (C) 2000 Elsevier Science B.V. All rights reserved.