N,N'-bis(o-hydroxbenzyl)-1,2-diamino-4,5-dimethylbenzene | 163122-31-4

• 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'-bis(o-hydroxbenzyl)-1,2-diamino-4,5-dimethylbenzene
• 英文别名: N,N'-bis(o-hydroxybenzyl)-1,2-diamino-(4,5-dimethyl)benzene；2,2'-[(4,5-Dimethyl-1,2-phenylene)bis(azanediylmethylene)]diphenol；2-[[2-[(2-hydroxyphenyl)methylamino]-4,5-dimethylanilino]methyl]phenol
• CAS: 163122-31-4
• 化学式: C₂₂H₂₄N₂O₂
• 分子量: 348.445
• InChiKey: VPVVAUNAVPTQBO-UHFFFAOYSA-N

物化性质

• 沸点：
  549.8±45.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  64.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(o-hydroxbenzyl)-1,2-diamino-4,5-dimethylbenzene 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Use of the Salan Ligands To Form Bimetallic Aluminum Complexes

  摘要：

  The syntheses and characterization of two types of complexes having a metal-Salan ligand stoichiometry of 2:1 (where Salan = N,N'-bis(o-hydroxybenzyl)-1,2-diaminoethane (SaleanH(4)), N,N'-bis(o-hydroxybenzyl)-1,2-diaminobenzene (SalophanH(4)), and N,N'-bis(o-hydroxybenzyl)-1,2-diamino-(4,5-dimethyl)benzene (SalomphanH(4))) are reported. The first are designated type I and are of the general formula LHAlR(AlR(2)), where L = Salean [R = Me (1), Et (2), (i)Bu (3)], Salophan [R = Me (4), Et (5), (i)Bu (6)], and Salomphan [R = Me (7), Et (8), (i)Bu (9)]. Formed by the thermolysis of RH from the type I complexes, the type II complexes are of the general formula [LAl(AlR(2))](2), where L = Salophan [R = Me (10), (i)Bu (11)] and Salomphan [R = Me (12), (i)Bu(13)]. The type I complexes can be converted into the trimetallic derivatives SalanAlR(AlR(2))(2) (type III) through the addition of AlR(3) while the type II cannot. One structurally characterized trimetallic complex, SalophanAlEt(AlEt(2))(2) (14), serves as a representative of this successful transformation.

  DOI：

  10.1021/om960505r

文献信息

• Use of Tetradentate (N2O2) Ligands To Form Monomeric, Trimetallic Gallium Complexes
  作者：David A. Atwood、Drew Rutherford

  DOI：10.1021/om00006a037

  日期：1995.6

  Members of the SalanH(4) class of tetradentate (N2O2) ligand, N,N'-bis(o-hydroxybenzyl)1,2-diaminoethane (SaleanH(4)), N,N'-bis(o-hydroxybenzyl)-1,3-diaminopropane (SalpanH(4)), N,N'-bis(o-hydroxybenzyl)-1,2-diaminobenzene (SalophanH(4), and N,N'-bis(o-hydroxybenzyl)1,2-diamino-4,5-dimethylbenzene (SalomphanH(4)), react with 3 equiv of GaMe(3) to form the trimetallic complexes SaleanGaMe(GaMe(2))(2) (1), SalpanGaMe(GaMe(2))(2): (2), SalophanGaMe(GaMe(2))(2) (3), and SalomphanGaMe(GaMe(2))(2) (4). Similar reactions of the SalanH(4) ligands with GaEt(3) form SaleanGaEt(GaEt(2))(2) (5), SalpanGaEt(GaEt(2))(2) (6), SalophanGaEt(GaEt(2))(2) (7), and SalomphanGaEt(GaEt(2))(2) (8). For these compounds, the H-1 NMR data indicate the presence of rigid solution state geometries. A crystallographic study of 1, 2, and 5 demonstrates that the molecules contain a central GaR group (R = Me, Et) which is coordinated in a planar array to the nitrogens and oxygens of the ligand. The remaining GaR(2) groups each bridge an oxygen and nitrogen atom. Compound 1 contains one molecule of toluene as solvent of crystallization. Crystal data are as follows. 1: C28H39Ga3N2O2, space group P2(1)/c (no. 14), with a = 10.694(2) Angstrom, b = 14.101(2) Angstrom, c = 19.184(2) Angstrom, beta = 94.040(10)degrees, V = 2885.5(7) Angstrom(3), and Z = 4. With 316 parameters refined on 2615 reflections having F > 4.0 sigma(F), the final R values were R = 0.0498 and R(w) = 0.0545. 2: C22H33Ga3N2O2, space Group P2(1)/c (no. 14), with a = 16.247(12) Angstrom, b = 9.588(9) Angstrom, c = 17.131(8) Angstrom, beta = 116.21(4)degrees, V = 2395(3) Angstrom(3) and Z = 4. With 262 parameters refined on 1777 reflections having F > 6.0 sigma(F), the final R values were R = 0.0690 and R(w) = 0.0763. 5: C26H41Ga3N2O2, space group monoclinic P2(1)/n (no. 14), with a = 8.433(1) Angstrom, b = 22.010(2) Angstrom, c = 15.241(1) Angstrom, beta = 98.81(1)degrees, V = 2795.4(5) Angstrom(3), and Z = 4. With 298 parameters refined on 2111 reflections having F > 4.0 sigma(F), the final R values were R = 0.0458 and R(w) = 0.0492.
• Synthesis and Structural Characterization of [(SalpanAl)Li(THF)2]2 and [(SalomphanAl)Li(THF)2]2: A New Class of Aluminum Anion
  作者：David A. Atwood、Drew Rutherford

  DOI：10.1021/ic00119a026

  日期：1995.7

  [(SalpanAl)Li(THF)(2)](2) (1) and [(SalomphanAl)Li(THF)(2)](2) (2) are two members of a new class of aluminum anion with metal-ligand stoichiometries of 1:1. Both compounds were spectroscopically and structurally characterized. In 1 (shown) the dihedral angles for the two AlLiO2 planes with respect to the central Al2N2 plane are +50.0 degrees (for Al(1) and -53.2 degrees (for Al(2)). This ''twist'' gives the molecule helical chirality.
• Trimetallic Aluminum and Gallium Alkyl Complexes with Tetradentate (N2O2) Ligands
  作者：David A. Atwood、Drew Rutherford

  DOI：10.1021/om00008a052

  日期：1995.8

  The present work describes the synthesis and characterization of a series of complexes of formula LAIR(AlR(2))(2) (R = Et, L = Salean (1), Salpan (2), Salophan (3), Salomphan (4); R = (i)Bu, L = Salean (5), Salpan (6), Salophan (7), Salomphan (8)). The use of the comparatively bulky (i)Bu group in 5 results in a complex which adopts a cis ligand configuration as shown by an X-ray structural analysis. The trimetallic complexes display H-1 NMR spectra that are consistent with a rigid solution-state geometry. The presence of a deshielding interaction between the protons on the alkyl group 13 reagent and the arylamine backbones of the Salophan and Salomphan ligands will be discussed. Additionally, the crystal structures of SalophanGaMe(GaMe(2))(2) (9) and SalomphanGaMe(GaMe(2))(2) (10) are reported.
• The Use of Tetradentate (N2O2) Ligands To Form Monomeric, Trimetallic Aluminum Complexes
  作者：David A. Atwood、Jolin A. Jegier、Kyli J. Martin、Drew Rutherford

  DOI：10.1021/om00003a054

  日期：1995.3

  Members of the SalanH(4) class of tetradentate (-N2O2) ligand, N,N'-bis(o-hydroxybenzyl)-1,2-diaminoethane (SaleanH(4)), N,N'-bis(o-hydroxybenzyl)-1,3-diaminopropane (SalpanH(4)), N,N'-bis(o-hydroxybenzyl)-1,2-diaminobenzene (SalophanH(4)), and N,N'-bis(o-hydroxybenzyl)-1,2-diamino-4,5-dimethylbenzene (SalomphanH(4)), demonstrate a wide range of chemistry with AlMe(3). For instance, SalpanH(4) will react with 1 and 2 equiv of AlMe(3) to produce the complexes SalpanH(2)(AlMe) (1) and [SalpanAl(AlMe(2))](2) (2), respectively. When 3 equiv of AlMe(3) is added to the appropriate ligand, the novel trimetallic derivatives Salean(AlMe)(A1Me(2))(2) (3), Salpan(AlMe)(AlMe(2))(2) (4), Salophan(AlMe)(AlMe(2))(2) (5), and Salomphan(AlMe)(AlMe(2))(2) (6) result. A general feature of 3-6 is the presence of a rigid solution-state geometry as evidenced by the H-1 NMR. A crystallographic study of 3 has shown that the molecules are comprised of a central AlMe group coordinated in a planar array to the nitrogens and oxygens of the ligand. The two AlMe(2) groups each bridge an oxygen and nitrogen atom. The overall morphology of 4 and 5 is similar to that shown for 3. However, structural characterization of 4 and 5 indicates that the AlMe(2) groups are inequivalent, with one bridging the two oxygens and the other bridging the two nitrogens. Crystal data for 3: C21H31Al3N(2)O(2), space group P ($) over bar 1 (No. 2) with a = 7.946(3) Angstrom, b = 9.662(3) Angstrom, c = 15.804(6) Angstrom, alpha = 89.192(8)degrees, beta = 84.434(6)degrees, gamma = 79.926(4)degrees, V = 1189.0(7) Angstrom(3) and Z = 2. With 253 parameters refined on 2954 reflections having F > 4.0 psi(F), the final R values were R = 0.0667 and R(w) = 0.0651. Crystal data for 4: C44H66Al6N4O4, space group P ($) over bar 1 (No. 2) with a = 7.821(7) Angstrom, b = 17.890(15) Angstrom, c = 18.668(16) Angstrom, alpha = 89.10(4)degrees, beta = 89.86(4)degrees, gamma = 89.78(5)degrees, V = 2612(4) Angstrom(3), and Z = 2. With 523 parameters refined on 2068 reflections having F > 4.0 sigma(F), the final R values were R = 0.0690 and R(w) = 0.0691. Crystal data for 5: C39H47Al3N2O2, space group monoclinic P2(1) (No. 4) with a =10.881(7) Angstrom, b = 17.170(10) Angstrom, c = 11.288(7) Angstrom, beta = 113.275(12)degrees, V = 1937(2) Angstrom(3) and Z = 2. With 401 parameters refined on 4313 reflections having F > 4.0 sigma(F), the final R values were R = 0.0619 and R(w) = 0.0642.
• Use of the Salan Ligands To Form Bimetallic Aluminum Complexes
  作者：David A. Atwood、Michael P. Remington、Drew Rutherford

  DOI：10.1021/om960505r

  日期：1996.10.29

  The syntheses and characterization of two types of complexes having a metal-Salan ligand stoichiometry of 2:1 (where Salan = N,N'-bis(o-hydroxybenzyl)-1,2-diaminoethane (SaleanH(4)), N,N'-bis(o-hydroxybenzyl)-1,2-diaminobenzene (SalophanH(4)), and N,N'-bis(o-hydroxybenzyl)-1,2-diamino-(4,5-dimethyl)benzene (SalomphanH(4))) are reported. The first are designated type I and are of the general formula LHAlR(AlR(2)), where L = Salean [R = Me (1), Et (2), (i)Bu (3)], Salophan [R = Me (4), Et (5), (i)Bu (6)], and Salomphan [R = Me (7), Et (8), (i)Bu (9)]. Formed by the thermolysis of RH from the type I complexes, the type II complexes are of the general formula [LAl(AlR(2))](2), where L = Salophan [R = Me (10), (i)Bu (11)] and Salomphan [R = Me (12), (i)Bu(13)]. The type I complexes can be converted into the trimetallic derivatives SalanAlR(AlR(2))(2) (type III) through the addition of AlR(3) while the type II cannot. One structurally characterized trimetallic complex, SalophanAlEt(AlEt(2))(2) (14), serves as a representative of this successful transformation.