N,N'-(ethane-1,2-diyl)bis(1-(4-tert-butylphenyl)methanimine) | 953426-65-8

• 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'-(ethane-1,2-diyl)bis(1-(4-tert-butylphenyl)methanimine)
• 英文别名: N,N'-bis(p-tert-butylbenzylidene)-1,2-diiminoethane；1-(4-tert-butylphenyl)-N-[2-[(4-tert-butylphenyl)methylideneamino]ethyl]methanimine
• CAS: 953426-65-8
• 化学式: C₂₄H₃₂N₂
• 分子量: 348.531
• InChiKey: LUOZRLVEMDTSOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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'-(ethane-1,2-diyl)bis(1-(4-tert-butylphenyl)methanimine) 在 甲醇 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 ethyl 1,4-bis(4-(tert-butyl)benzyl)piperazine-2-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of novel cYY analogues targeting Mycobacterium tuberculosis CYP121A1

  摘要：

  The rise in multidrug resistant (MDR) cases of tuberculosis (TB) has led to the need for the development of TB drugs with different mechanisms of action. The genome sequence of Mycobacterium tuberculosis (Mtb) revealed twenty different genes coding for cytochrome P450s. CYP121A1 catalyzes a C-C crosslinking reaction of di-cyclotyrosine (cYY) producing mycocyclosin and current research suggests that either mycocyclosin is essential or the overproduction of cYY is toxic to Mtb. A series of 1,4-dibenzyl-2-imidazol-1-yl-methylpiperazine derivatives were designed and synthesised as cYY mimics. The derivatives substituted in the 4-position of the phenyl rings with halides or alkyl group showed promising antimycobacterial activity (MIC 6.25 mu g/mL), with the more lipophilic branched alkyl derivatives displaying optimal binding affinity with CYP121A1 (Pr-i K-D = 1.6 mu M; Bu-t K-D = 1.2 mu M). Computational studies revealed two possible binding modes within the CYP121A1 active site both of which would effectively block cYY from binding.

  DOI：

  10.1016/j.bmc.2019.02.051
• 作为产物：
  描述：

  对叔丁基苯甲醛 、 乙二胺 以 乙醇 为溶剂， 生成 N,N'-(ethane-1,2-diyl)bis(1-(4-tert-butylphenyl)methanimine)
  参考文献：
  名称：

  钯 (II) 的 N,N'-螯合配体配合物中的双同构结构

  摘要：

  螯合二苯甲醛亚胺配体与 Pd(OAc) 2配位得到1 H NMR 光谱，其表明芳环邻位氢与钯中心的双拮抗相互作用。DFT 计算表明，在固态下，两种相互作用都发生在配位平面上方，每个芳环的一个邻位氢与 Pd 和相邻的乙酸根配体配位氧非常接近。

  DOI：

  10.1002/ejic.202200027

文献信息

• Thermally latent reaction of hemiacetal ester with epoxide controlled by Schiff-base–zinc chloride complexes with tunable catalytic activity
  作者：Hiroyuki Komatsu、Bungo Ochiai、Tetsuo Hino、Takeshi Endo

  DOI：10.1016/j.molcata.2007.04.016

  日期：2007.8

  Schiff-base-zinc chloride complexes (ZnCl2/1(R)) thermal-latently catalyze the reaction of glycidyl phenyl ether (2) and I -propoxyethyl-2ethylhexanate (3) that proceeds at appropriate temperatures for latent curing. This reaction proceeds via the nucleophilic addition of carboxylic acid generated from the thermal dissociation of 3 to'2, which takes place faster than the reaction without (ZnCl2/1(R)). Catalytic activities of (ZnCl2/1(R)), depending on the basicities of the a-diimine ligands controllable by the substituents on the aromatic rings, were evaluated by kinetic parameters; namely the reaction rate constants (k), the activation energies (E-a), and the frequency factors (A). (ZnCl2/1(R)) bearing the electron-withdrawing chlorine group initiates the reaction above 80 degrees C, whereas (ZnCl2/1(OMe)), bearing the electron-donating methoxy group initiates the reaction above 100 degrees C. The E-a values in the reactions with (ZnCl2/1(Cl)) and (ZnCl2/1(OMe)), were estimated to be 52.2 and 177 kJ mol(-1), respectively, which agree with the latencies at ambient temperatures. The A values also differ with the catalysts (6.46 x 10(2) and 2.04 x 10(19) L mol(-1) s(-1) for (ZnCl2/1(Cl)) and (ZnCl2/1(OMe)), respectively). The very high A values for the catalysts with electron-donating groups manifest the very good latencies under ambient conditions, in spite of the high activities at elevated temperatures. The coordination behavior of (ZnCl2/1(R)) was evaluated by H-1 NMR, C-13 NMR, N-15 NMR, and lR spectroscopies to understand the substituent effects. (C) 2007 Elsevier B.V. All rights reserved.
• <i>Bis</i> ‐Anagostic Structures in N,N’‐Chelate Ligand Complexes of Palladium(II)
  作者：M. Arif Sajjad、Peter Schwerdtfeger、Yichao Cai、Joyce M. Waters、John A. Harrison、Alastair J. Nielson

  DOI：10.1002/ejic.202200027

  日期：2022.4.27

  dibenzaldimine ligands on coordination to Pd(OAc)2 give 1H NMR spectra which indicate bis-anagostic interactions of the aromatic ring ortho-hydrogens with the palladium centre. DFT calculations show that in the solid state, both interactions occur above the coordination plane with one ortho-hydrogen of each aromatic ring making close approaches to Pd and the adjacent acetato ligand coordinating oxygens

  螯合二苯甲醛亚胺配体与 Pd(OAc) 2配位得到1 H NMR 光谱，其表明芳环邻位氢与钯中心的双拮抗相互作用。DFT 计算表明，在固态下，两种相互作用都发生在配位平面上方，每个芳环的一个邻位氢与 Pd 和相邻的乙酸根配体配位氧非常接近。
• Synthesis and biological evaluation of novel cYY analogues targeting Mycobacterium tuberculosis CYP121A1
  作者：Safaa M. Kishk、Kirsty J. McLean、Sakshi Sood、Mohamed A. Helal、Mohamed S. Gomaa、Ismail Salama、Samia M. Mostafa、Luiz Pedro S. de Carvalho、Andrew W. Munro、Claire Simons

  DOI：10.1016/j.bmc.2019.02.051

  日期：2019.4

  The rise in multidrug resistant (MDR) cases of tuberculosis (TB) has led to the need for the development of TB drugs with different mechanisms of action. The genome sequence of Mycobacterium tuberculosis (Mtb) revealed twenty different genes coding for cytochrome P450s. CYP121A1 catalyzes a C-C crosslinking reaction of di-cyclotyrosine (cYY) producing mycocyclosin and current research suggests that either mycocyclosin is essential or the overproduction of cYY is toxic to Mtb. A series of 1,4-dibenzyl-2-imidazol-1-yl-methylpiperazine derivatives were designed and synthesised as cYY mimics. The derivatives substituted in the 4-position of the phenyl rings with halides or alkyl group showed promising antimycobacterial activity (MIC 6.25 mu g/mL), with the more lipophilic branched alkyl derivatives displaying optimal binding affinity with CYP121A1 (Pr-i K-D = 1.6 mu M; Bu-t K-D = 1.2 mu M). Computational studies revealed two possible binding modes within the CYP121A1 active site both of which would effectively block cYY from binding.