N,N′-diphenyl-N,N′-bis(pyridin-2-ylmethyl)ethane-1,2-diamine | 54172-96-2

• 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′-diphenyl-N,N′-bis(pyridin-2-ylmethyl)ethane-1,2-diamine
• 英文别名: N,N'-Dibenzyl-N,N'-diphenyl-1,2-diamino-aethan；N,N'-dibenzyl-N,N'-diphenyl-ethylenediamine；N,N'-Dibenzyl-N,N'-diphenyl-aethylendiamin；N,N'-dibenzyl-N,N'-diphenylethane-1,2-diamine
• CAS: 54172-96-2
• 化学式: C₂₈H₂₈N₂
• 分子量: 392.544
• InChiKey: BEMVSIFKKAAKFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  6.48
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N,N′-diphenyl-N,N′-bis(pyridin-2-ylmethyl)ethane-1,2-diamine 、 6-硝基藜芦醛 在 2,6-二甲基吡啶 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 7.0h， 以64.2%的产率得到((ethane-1,2-diylbis((pyridin-2-ylmethyl)azanediyl))bis(4,1-phenylene))bis((4,5-dimethoxy-2-nitrophenyl)methanol)
  参考文献：
  名称：

  Increasing the Dynamic Range of Metal Ion Affinity Changes in Zn²⁺Photocages Using Multiple Nitrobenzyl Groups

  摘要：

  Two generations of DiCast photocages that exhibit light-induced decreases in metal ion affinity have been prepared and characterized. Expansion of the common Zn2+ chelator of N,N-dipicolylaniline (DPA) to include additional aniline ligand provides N,N'-diphenyl-N,N'-bis(pyridin-2-ylmethyl)ethane-1,2-diamine, a tetradentate ligand that was functionalized with two photolabile groups to afford DiCast-1. Uncaging of the nitrobenzhydrol reduces the electron density on two metal bound aniline ligands, which decreases the Zn2+ affinity 190 fold The analogous MonoCast photocage with a single nitrobenzhydrol group only undergoes a 14 fold reduction in affinity after an identical photochemical transformation. A second series of DiCast photocages based on a N,Ni-(pyridine-2,6-diylbis(methylene))dianiline scaffold, which allows the introduction of two additional Zn2+-binding ligands into a preorganized chelator, expand on the multi-photolabile group strategy. DiCast-2 includes two pyridine ligands while DiCast-3 adds two carboxylate groups. Addition of bridging pyridine to the second generation photocages leads to more stable Zn2+ complexes, and photolysis of two photolabile groups increases the Zn2+ affinity changes to 480 fold The Zn2+, Cu2+, and Cd2+ binding properties were examined in all the DiCast photocages and the corresponding photoproducts using UV-vis spectroscopy. Further insight into the photocage Zn2+-binding motifs was obtained by X-ray analysis of DiCast-2 and DiCast-3 model ligands.

  DOI：

  10.1021/ic400465g
• 作为产物：
  描述：

  N-甲基-N-亚硝基苯胺 生成 N,N′-diphenyl-N,N′-bis(pyridin-2-ylmethyl)ethane-1,2-diamine
  参考文献：
  名称：

  SEEBACH D.; DACH R.; ENDERS D.; RENGER B.; JANSEN M.; BRACHTEL G., HELV. CHIM. ACTA, 1978, 61, NO 5, 1628-1647

  摘要：

  DOI：

文献信息

• 1, 4, 5, 6-Tetrahydro-?-tetrazin-Derivate
  作者：Dieter Seebach、Rolf Dach、Dieter Enders、Bernd Renger、Martin Jansen、Gerold Brachtel

  DOI：10.1002/hlca.19780610512

  日期：1978.7.12

  1, 4, 5, 6‐Tetrahydro‐ν‐tetrazin‐DerivateThe title compounds 2 and 13 are readily available from α‐lithiated N‐alkyl‐nitrosoamines 1 (see Tables 1 and 2) which decompose at − 73° to yield the N‐oxides 2. The ESR. spectra of two derivatives 1 are recorded (Fig. 1), and tentative mechanisms are proposed for the head to head dimerizations (la‐ 3‐ 4‐ 5‐ 2a and Scheme 1). Coupling of lithionitrosoamines with iodine (‐6) and alternative decomposition routes of representatives of this class of organometallics with special substitution [equations (2)‐(5)] are reported.The structures of the tetrazines are established by spectroscopic data [ESCA] (Fig. 2), IR., UV., 1H‐ (cf. Fig. 9) and 13C‐NMR., PE. (Scheme 2), by an X‐ray analysis of 2a (Fig. 4‐8 and Table 3), and by the chemical reactions. The crystal structure of 2a is a twisted boat with non planar terminal nitrogen atoms which reflects the electron repulsion in the 4‐atom‐6‐electron NNNN‐system. Comparisons are made with 2‐tetrazenes, the open chain analogues of 13, wherever possible. Raney‐Ni reductions of 2 or 13 gives diamines 14 to which is assigned the d, l‐configuration through the 1H‐NMR. spectra of the aminals 7 and 15. Neither the oxides 2 nor the tetrazines 13 undergo cycloaddition reactions [equation (6) and Section 4].Compound 2a is dimerized to the bis (nitrosoamino)‐2‐tetrazene 18 by treatment with acid, ZnII, CuI or iodomethane. 2a is oxidized at nitrogen to the ethylene diamine derivative 6a (through 20, with H2O2), or at the CH2‐groups of the ring to give oxo‐N‐oxide 21 (with MnO2 or the ring contracted oxo‐tetrazoline‐N‐oxide 22 (with KMnO4).Pyrolysis or photolysis of the dimethyl tetrahydrotetrazine 13a furnishes the trimer 26 of N‐methylimine, but no diazetidine 27. Silver and mercury complexes 29 are obtained from 13a, while Cr(CO)5. THF does not furnish a complex as with azocompounds, but rather replaces N2 in 13a by CO (→ 28). Oxidation with permanganate converts 13a into the oxalic acid derivative 30 with unchanged tetrazine structure.
• van Rijn, Chemisches Zentralblatt, 1898, vol. 69, # I, p. 381
  作者：van Rijn

  DOI：——

  日期：——