N-(mesitylethyl)-1,4,7,10-tetraazacyclododecane | 423773-92-6

• 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-(mesitylethyl)-1,4,7,10-tetraazacyclododecane
• 英文别名: 1-[2-(2,4,6-trimethylphenyl)ethyl]-1,4,7,10-tetrazacyclododecane
• CAS: 423773-92-6
• 化学式: C₁₉H₃₄N₄
• 分子量: 318.506
• InChiKey: BVIBTVMRZNOWGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  39.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  copper(II) perchlorate hexahydrate 、 乙醇 、 N-(mesitylethyl)-1,4,7,10-tetraazacyclododecane 以 乙醇 为溶剂， 以54%的产率得到[(N-(mesitylethyl)-1,4,7,10-tetraazacyclododecane)copper(II)](PF6)2*0.5ethanol
  参考文献：
  名称：

  The synthesis of small azamacrocycles bearing pendant aromatic functionalities.

  摘要：

  A simple synthetic procedure for the mono- or di-functionalization of tri- and tetra-azamacrocycles with electron rich arenes has been developed. Specifically, 1,4,7-triazacyclononane (tacn), 1,4,7, 10-tetraazacyclododecane (cyclen) and 1 4,8,11-tetraazacyclotetradecane (cyclam) react with 2,4,6-trimethylstyrene in the presence of n-butyllithium to give, respectively N-(mesitylethyl)-1,4,7-triazacyclononane (L-1), N-(mesitylethyl)-1,4,7,10-tetraazacyclododecane (L-4), and N-(mesitylethyl)-1,4,8,11-tetraazacyclotetradecane (L-5). In contrast, when styrene itself or p-vinylanisole are used as the Michael acceptor with 1,4,7-triazacyclononane. the N',N" product is formed, respectively N',N"-bis(phenylethyl)-1,4,7-triazacyclononane (L-2) and N',N"-bis(p-methoxyphenylethyl)-1,4,7-triazacyclononane (L-3). Using conventional mono-functionalization techniques, the phenyl derivatives N-(4-hydroxymethylbenzyl)-1,4,7-triazacyclononane (L-6) and N-(4-benzylcarboxylic acid)-1, 4,7-triazacyclononane (L,) have also been synthesised. A series of transition metal complexes of L-1 to L-7 with Ni(II), Cu(II), Zn(II) and Co(II) have been prepared. The X-ray crystal structures of [Cu(L-1)(2)](PF6)(2), [(L-1)CuCl2], [Cu(L-6)(NO3)(2)] and [Cu-2(L-7-H)(2)(OH2)(2)](PF6)(2).3H(2)O are described. In all of these complexes, coordination to the metal takes place through the macrocycle nitrogens. The crystal structure of [Cu-2(L-7-H)(2)(OH2)(2)](PF6)(2).3H(2)O reveals that it is a coordinate-polymeric material. Attempts to coordinate the pendent arenes to Rh(I) are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0277-5387(01)00994-9

文献信息

• The synthesis of small azamacrocycles bearing pendant aromatic functionalities.
  作者：Andrew C Benniston、David Ellis、Louis J Farrugia、Roselyn Kennedy、Robert D Peacock、Sarah Walker

  DOI：10.1016/s0277-5387(01)00994-9

  日期：2002.2

  A simple synthetic procedure for the mono- or di-functionalization of tri- and tetra-azamacrocycles with electron rich arenes has been developed. Specifically, 1,4,7-triazacyclononane (tacn), 1,4,7, 10-tetraazacyclododecane (cyclen) and 1 4,8,11-tetraazacyclotetradecane (cyclam) react with 2,4,6-trimethylstyrene in the presence of n-butyllithium to give, respectively N-(mesitylethyl)-1,4,7-triazacyclononane (L-1), N-(mesitylethyl)-1,4,7,10-tetraazacyclododecane (L-4), and N-(mesitylethyl)-1,4,8,11-tetraazacyclotetradecane (L-5). In contrast, when styrene itself or p-vinylanisole are used as the Michael acceptor with 1,4,7-triazacyclononane. the N',N" product is formed, respectively N',N"-bis(phenylethyl)-1,4,7-triazacyclononane (L-2) and N',N"-bis(p-methoxyphenylethyl)-1,4,7-triazacyclononane (L-3). Using conventional mono-functionalization techniques, the phenyl derivatives N-(4-hydroxymethylbenzyl)-1,4,7-triazacyclononane (L-6) and N-(4-benzylcarboxylic acid)-1, 4,7-triazacyclononane (L,) have also been synthesised. A series of transition metal complexes of L-1 to L-7 with Ni(II), Cu(II), Zn(II) and Co(II) have been prepared. The X-ray crystal structures of [Cu(L-1)(2)](PF6)(2), [(L-1)CuCl2], [Cu(L-6)(NO3)(2)] and [Cu-2(L-7-H)(2)(OH2)(2)](PF6)(2).3H(2)O are described. In all of these complexes, coordination to the metal takes place through the macrocycle nitrogens. The crystal structure of [Cu-2(L-7-H)(2)(OH2)(2)](PF6)(2).3H(2)O reveals that it is a coordinate-polymeric material. Attempts to coordinate the pendent arenes to Rh(I) are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.