cis,cis-1,3,5-triaminocyclohexane | 26150-46-9

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cis,cis-1,3,5-triaminocyclohexane
• CAS: 26150-46-9
• 化学式: C₆H₁₅N₃
• 分子量: 129.205
• InChiKey: UYAUGHKQCCCFDK-FPFOFBBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.85
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  78.06
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis,cis-1,3,5-triaminocyclohexane 在 palladium on activated charcoal 氢气 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 273.0h， 生成 9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid [6-(cis-3,5-(N,N-di-tert-butyloxycarbonyl)diaminocyclohexylamino)hexyl]amide
  参考文献：
  名称：

  Toward Efficient Zn(II)-Based Artificial Nucleases

  摘要：

  A series of cis-cis-triaminocyclohexane Zn(II) complex-anthraquinone intercalator conjugates, designed in such a way to allow their easy synthesis and modification, have been investigated as hydrolytic cleaving agents for plasmid DNA. The ligand structure comprises a triaminocyclohexane platform linked by means of alkyl spacers of different length (from C-4 to C-8) to the anthraquinone group which may intercalate the DNA. At a concentration of 5 muM, the complex of the derivative with a C-8 alkyl spacer induces the hydrolytic stand scission of supercoiled DNA with a rate of 4.6 x 10(-6) s(-1) at pH 7 and 37 degreesC. The conjugation of the metal complex with the anthraquinone group leads to a 15-fold increase of the cleavage efficiency when compared with the anthraquinone lacking Zn-triaminocyclohexane complex. The straightforward synthetic procedure employed, allowing a systematic change of the spacer length, made possible to gain more insight on the role of the intercalating group in determining the reactivity of the systems. Comparison of the reactivity of the different complexes shows a remarkable increase of the DNA cleaving efficiency with the length of the spacer. In the case of too-short spacers, the advantages due to the increased DNA affinity are canceled due to the incorrect positioning of the reactive group, thus leading to cleavage inhibition.

  DOI：

  10.1021/ja039465q
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 乙醇 、 sodium 作用下， 生成 cis,cis-1,3,5-triaminocyclohexane
  参考文献：
  名称：

  Hassel; Lunde, Research (London), 1950, vol. 3, p. 484

  摘要：

  DOI：

文献信息

• The crystal structures of glycylglycine and glycine complexes of cis,cis-1,3,5-triaminocyclohexane–copper(II) as reaction intermediates of metal-promoted peptide hydrolysis
  作者：Xiang Shi Tan、Yuki Fujii、Tsuyoshi Sato、Yoshiharu Nakano、Morio Yashiro

  DOI：10.1039/a901569h

  日期：——

  The glycylglycine and glycine complexes of cis,cis-1,3,5-triaminocyclohexane–copper(II), model reaction intermediates of peptide hydrolysis by CuII–triamine complexes, have been synthesized and characterized by X-ray crystallography.

  甘氨酰甘氨酸和甘氨酸与顺式,顺式-1,3,5-三氨基环己烷铜(II)的络合物，作为铜(II)三胺复合物催化肽水解的模型反应中间体，已被合成并通过X射线晶体学进行表征。
• Lipophilic hexadentate gallium, indium and iron complexes of new phenolate-derivatized cyclohexanetriamines as potential in vivo metal-transfer reagents
  作者：James E. Bollinger、Joel T. Mague、Charles J. O′Connor、William A. Banks、D. Max Roundhill

  DOI：10.1039/dt9950001677

  日期：——

  compounds with gallium(III), indium(III) and iron(III) salts gave neutral six-co-ordinate N3O3 complexes of type [ML](M = Ga, In or Fe). The complexes have been characterized by a combination of infrared, 1H and 13C-1H} NMR and mass spectroscopy. The distribution coefficients between octan-1-ol and water indicate that the complexes are lipophilic. The electronic absorption spectra of the high-spin

  通过顺式-1,3,5-三氨基环己烷与取代的水杨醛之间的席夫碱缩合反应合成了1,3,5-三（5-取代的水杨基氨基）环己烷（H 3 L； R = H，NO 2或OMe），然后用KBH 4还原。这些化合物与镓（III），铟（III）和铁（III）盐反应，得到中性的六坐标N 3 O 3络合物，类型为[ML]（M = Ga，In或Fe）。配合物的特征是红外，1 H和13 C- 11 H NMR和质谱。octan-1-ol与水之间的分配系数表明，该配合物具有亲脂性。高自旋铁（III）配合物的电子吸收光谱显示在450-500 nm范围内的配体到金属的电荷转移带。五个配合物的结构已通过单晶X射线晶体学确认。
• Cytotoxic (<i>cis</i>,<i>cis</i>-1,3,5-triaminocyclohexane)ruthenium(<scp>ii</scp>)-diphosphine complexes; evidence for covalent binding <i>and</i> intercalation with DNA
  作者：Dan E. Wise、Aimee J. Gamble、Sham W. Arkawazi、Paul H. Walton、M. Carmen Galan、Michael P. O'Hagan、Karen G. Hogg、Joanne L. Marrison、Peter J. O'Toole、Hazel A. Sparkes、Jason M. Lynam、Paul G. Pringle

  DOI：10.1039/d0dt02612c

  日期：——

  with biologically relevant duplex and quadruplex DNA models correlate with the activity observed with A549, A2780 and 293T cell lines, and the degree of activity was found to be sensitive to the chelating diphosphine ligand. A label-free ptychographic cell imaging technique recorded cell death processes over 4 days. The Ru(II) cis-tach diphosphine complexes exhibit anti-proliferative effects, in some cases

  我们报告了具有通式 [RuCl( cis -tach)(diphosphine)] + ( cis -tach = cis – cis -1,3,5 - triaminocyclohexan) 的细胞毒性钌 ( II ) 配合物，其特征在于1 H, 13 C和31 P 1 H} NMR光谱、质谱、X射线晶体学和元素分析。研究了活性物质的水合动力学和稳定性，表明氯配体在 298 K 下被水取代，一级速率常数为 10 -2 –10 -3 s -1，非常适合作为抗肿瘤剂的潜在临床用途。与生物相关双链和四链 DNA 模型的强相互作用与在 A549、A2780 和 293T 细胞系中观察到的活性相关，并且发现活性程度对螯合二膦配体敏感。一种无标记的 ptychographic 细胞成像技术记录了超过 4 天的细胞死亡过程。Ru( II ) cis- tach 二膦配合物表现出抗增殖作用，在某些情况下优于顺铂和其他细胞毒性钌配合物。
• One-Pot Synthesis of Dihydroimidazo- and Imidazophenanthridinium Salts
  作者：Alexis Parenty、Leroy Cronin

  DOI：10.1055/s-2007-983895

  日期：2008.1

  Two highly efficient and general one-pot annulation reactions are described for the synthesis of dihydroimidazo- and imidazophenanthridinium salts (DIPs + and IPs +). These two methodologies exploit the difference in reactivity between primary amino-based or ammonia nucleophiles and the dielectrophilic starting material, 2-bromoethylphenanthridinium bromide.

  报道了两种高效且通用的“一锅法”环化反应，用于合成二氢咪唑并[二氢]菲啶盐（DIPs⁺和IPs⁺）。这两种方法利用了基于伯胺或氨的亲核试剂与二电子亲电起始物2-溴乙基菲啶溴化物之间的反应活性差异。
• Cu(i) complexes based on cis, cis-1,3,5-tris(arylideneamino)cyclohexane ligands: synthesis, structure and CO binding
  作者：Parisa Ebrahimpour、Michael Cushion、Mairi F. Haddow、Andrew J. Hallett、Duncan F. Wass

  DOI：10.1039/c0dt00986e

  日期：——

  with [Cu(NCCH3)4]PF6 gives Cu(I) complexes of tach-based ligands 2.2–9.2, eg; 2.2; [Cu(2.1)(NCCH3)]PF6}. Displacement of the acetonitrile ligand by CO was achieved successfully for all the Cu(I) complexes of tach-based ligands and the resulting complexes have been shown to bind carbon monoxide 2.3–9.3, eg; 2.3; [Cu(2.1)(CO)]PF6}. The X-ray single crystal structures of 5.1, 8.1, 9.1, 3.2, 7.2, 8.2

  一系列新的空间庞大的，基于面部配位的N 3-供体基于tach的配体（tach；顺式，顺式-1,3,5-三氨基环己烷）[ 2.1 ;顺式，顺式-1,3,5-三（2,4-二甲基亚苄基氨基）环己烷，4.1 ;顺式，顺式-1,3,5-三（五甲基亚苄基氨基）环己烷，5.1 ;顺式，顺式-1,3,5-三（2,6-二甲氧基苄叉亚氨基）环己烷，6.1 ;顺式，顺式-1,3,5-三（五氟亚苄基氨基）环己烷，7.1 ;顺式，顺式-1,3,5-三（3,5-双（二三氟甲基）亚苄基氨基）环己烷，8.1 ;顺式，顺式-1,3,5-三（2-三氟甲基亚苄基氨基）环己烷，9.1 ;顺式，顺式-1,3,5-三（2-甲氧基苄亚氨基）环己烷]是从塔赫与三当量的适当取代基的缩合中获得的 苯甲醛。与[Cu（NCCH 3）4 ] PF 6反应得到铜（I）基于tach的配体的复合物 2.2–9.2，例如；2.2 ; [Cu（2.1）（NCCH