N-mesityl-ortho-tert-butylsalicylaldimine | 500556-51-4

• 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-mesityl-ortho-tert-butylsalicylaldimine
• 英文别名: 2-tert-butyl-6-[(2,4,6-trimethylphenylimino)methyl]phenol；N-(3-tert-butyl-2-hydroxy)benzylidene(2,4,6-trimethyl)aniline；2-tBu-6-[(2,4,6-Me3C6H2)NCH]C6H3OH；2-Tert-butyl-6-[(2,4,6-trimethylphenyl)iminomethyl]phenol
• CAS: 500556-51-4
• 化学式: C₂₀H₂₅NO
• 分子量: 295.425
• InChiKey: WXRANIYHKBRBSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-mesityl-ortho-tert-butylsalicylaldimine 、 以 正己烷 为溶剂， 以68%的产率得到
  参考文献：
  名称：

  Synthesis and thermal reactivity of organoscandium and yttrium complexes of sterically less bulky salicylaldiminato ligandsElectronic supplementary information (ESI) available: Further experimental details. See http://www.rsc.org/suppdata/dt/b3/b303097k/

  摘要：

  通过烷烃消去法，从[M(CH2SiMe2R)3(THF)2]（R = Me，Ph）和两个当量的蛋白配体（HL）制备了 N-苯基（L1）、N-2-异丙基苯基（L2）和 N-甲烷基（L3）取代的正叔丁基水杨醛二烷基配体的钪和钇双(配体)单(烷基)配合物。生成的[L2M(THF)n(CH2SiMe2R)]（n = 0-2，L = L1 (1)、L2 (2)、L3 (3)）复合物热不稳定，在 -20 至 20 °C 之间迅速分解。为了深入了解在早期过渡金属有机金属化学中赋予热稳定性所必需的配体特征，我们研究了 1-3 复合物的分解途径，并将其与立体性更强的 N-2,6-二异丙基苯基取代类似物进行了比较。化合物 1 和 2 通过整个 CH2SiMe2R 基团向醛二胺碳的 1,3 迁移，在室温下迅速而干净地分解。相比之下，L3 单（烷基）3 通过正交-C6H2Me3 基团的金属化作用分解得很干净。在钇的情况下，金属化的烷基随后会发生 1,3 迁移到醛亚胺碳上，形成一个五元 C4N 环。

  DOI：

  10.1039/b303097k
• 作为产物：
  描述：

  3-叔丁基-2-羟基苯甲醛 、 2,4,6-三甲基苯胺 在 zinc(II) chloride 作用下， 以 苯 为溶剂， 反应 12.0h， 以80%的产率得到N-mesityl-ortho-tert-butylsalicylaldimine
  参考文献：
  名称：

  Synthesis and thermal reactivity of organoscandium and yttrium complexes of sterically less bulky salicylaldiminato ligandsElectronic supplementary information (ESI) available: Further experimental details. See http://www.rsc.org/suppdata/dt/b3/b303097k/

  摘要：

  通过烷烃消去法，从[M(CH2SiMe2R)3(THF)2]（R = Me，Ph）和两个当量的蛋白配体（HL）制备了 N-苯基（L1）、N-2-异丙基苯基（L2）和 N-甲烷基（L3）取代的正叔丁基水杨醛二烷基配体的钪和钇双(配体)单(烷基)配合物。生成的[L2M(THF)n(CH2SiMe2R)]（n = 0-2，L = L1 (1)、L2 (2)、L3 (3)）复合物热不稳定，在 -20 至 20 °C 之间迅速分解。为了深入了解在早期过渡金属有机金属化学中赋予热稳定性所必需的配体特征，我们研究了 1-3 复合物的分解途径，并将其与立体性更强的 N-2,6-二异丙基苯基取代类似物进行了比较。化合物 1 和 2 通过整个 CH2SiMe2R 基团向醛二胺碳的 1,3 迁移，在室温下迅速而干净地分解。相比之下，L3 单（烷基）3 通过正交-C6H2Me3 基团的金属化作用分解得很干净。在钇的情况下，金属化的烷基随后会发生 1,3 迁移到醛亚胺碳上，形成一个五元 C4N 环。

  DOI：

  10.1039/b303097k

文献信息

• Monocyclopentadienyl phenoxy-imine and phenoxy-amine complexes of titanium and zirconium and their application as catalysts for 1-alkene polymerisation
  作者：Robyn K.J Bott、David L Hughes、Mark Schormann、Manfred Bochmann、Simon J Lancaster

  DOI：10.1016/s0022-328x(02)02106-x

  日期：2003.1

  Deprotonation of the phenol-imines 2-Bu'-6-(RNCH)C6H3OH (R = 2,4,6-Me3C6H2 (1a), C6F5 (1b), C6H11 (1c) and phenolamines 2,4-Bu'(2)-6-(R'NCH2)C6H2OH (R' = C4H8 (1d), C5H10 (1e)) with n -BuLi gives the corresponding lithium phenoxides. The reaction with MCl4 in THF solution leads to the bis(ligand) complexes 2-Bu'-6-(RNCH)C6H3H3O}(2)MCl2 and 2,4-Bu'(2)-6-(R'NCH2)C6H2O}(2)MCl2 (M=Ti: 2a, 2d, 2e, Zr: 3a, 3d and 3e). The cyclopentadienyl phenoxy-imine and -amine complexes Cp2-Bu'-6-(RNCH)C6H3O}MCl2 and Cp2,4-Bu'(2)-6-(R'NCH2)C6H2O}MCl2 (M = Ti: 4a-4e, Zr: 5a-5e) were prepared similarly through reaction with CPMCl3. The crystal and molecular structures of 2a, 3a, 4a and 4c have been determined. 2a and 3a are isostructural and exhibit a distorted octahedral geometry. 4a has a distorted square-pyramidal structure whereas 4e is essentially tetrahedral and the nitrogen does not coordinate. All new complexes are active for the polymerisation of ethene when activated with methyaluminoxane. 4b, 5a, 5d and 5e are active for the copolymerisation of ethene and 1-hexene and the oligomerisation of 1-hexene. (C) 2002 Elsevier Science B.V. All rights reserved.
• Synthesis, structure and catalytic activity of new iminophenolato complexes of scandium and yttrium
  作者：Agustı́n Lara-Sanchez、Antonio Rodriguez、David L Hughes、Mark Schormann、Manfred Bochmann

  DOI：10.1016/s0022-328x(02)01657-1

  日期：2002.12

  The reaction of equimolar amounts of 2-(2,4,6-Me3C6H2N = CH)(6-Bu')C6H3OH (HL') with M(CH2SiMe3)(3)(THF)(3) (M = Sc or Y) under mild conditions gives M(CH2SiMe3)(2)(THF)(L-1). The trigonal-bipyramidal structure of these dialkyls was confirmed crystallographically for M = Sc. Whereas the scandium complex is stable in solution at room temperature, the yttrium derivative slowly disproportionates to give Y(L-1)(3) which is also accessible from Y(CH2SiMe3)(3)(THF)(3) and three HL'. The X-ray structure of Y(L)3 indicates a chiral tris-chelate complex. While the reaction of the related ligand (2-CyN = CH)(6-Bu')C6H3OH (HL2, CY = cyclohexyl) with Sc(CH2SiMe3)(3)(THF)(3) gives the expected dialkyl Sc(CH2SiMe3)(2)(THF)(L-2), the reaction with the yttrium analogue affords the six-coordinate monoalkyl product Y(CH2SiMe3)(THF)(L-2)(2). This product is stable in solution towards disproportionation. The reaction of Y[N(SiMe3)(2)](3) with (2-C6F5N = CH)(6-Bu')C6H3OH (HL3) affords YN(SiMe3)(2)}(L-3)(2) and Y(L-3)(3). Both complexes are seven-coordinate in the solid state due to Y...F co-ordination to the C6F5 substituents. The scandium alkyl complexes are efficient catalysts for the ring-opening polymerisation of F-caprolactone. (C) 2002 Elsevier Science B.V. All rights reserved.
• Ring-opening polymerization of various cyclic esters by Al complex catalysts containing a series of phenoxy-imine ligands: Effect of the imino substituents for the catalytic activity
  作者：Naruhito Iwasa、Michiya Fujiki、Kotohiro Nomura

  DOI：10.1016/j.molcata.2008.06.009

  日期：2008.9

  Ring-opening polymerizations (ROPs) of various cyclic esters [epsilon-caprolactone (CL), delta-valerolactone (VL), rac-lactide (LC)] using a series of Al complexes containing phenoxy-imine ligands of type, Me2Al[O-2-Bu-t-6-(RN=CH)C6H3 ], [R=Bu-t (1a), cyclohexyl (1b), adamantyl (1c), C6H5 (1d), 2,6-Me2C6H3 (1e),2,6-(Pr2C6H3)-Pr-i (1f), 2,4,6-Me3C6H2 (1g), 2,4,6-(Bu3C6H2)-Bu-t (1h), C6F5 (1i)], have been explored in the presence of (BuOH)-Bu-n. Synthesis and identification of 1g and 1h including structural analysis of 1g by X-ray crystallography have also been explored. Both the catalytic activity and the catalyst efficiency in the ROPs were found to be highly affected by the imino substituents (R) employed. The 2,4,6-(Bu3C6H2)-Bu-t analogue (1h) showed the notable catalytic activity in spite of its low catalyst efficiency in the ROP of CL, and the C6F5 analogue (1i) was most effective in terms of both the activity and the efficiency. The C6F5 analogue (1i) also showed the highest catalytic activity for the ROP of VL, and the polymerization proceeded in a living manner. The C6F5 analogue also showed relatively high catalytic activity in the ROP of LC, but the resultant polymer had no stereo-regularity. Although the Al complexes containing alkyl substituents (1a-c) exhibited low or negligible catalytic activities in the ROPs of CL and VL, the cyclohexyl analogue (1b) showed moderate catalytic activity for the ROP of LC. Attempts for the ROP of beta-butyrolactone (beta-BL) and gamma-butyrolactone (gamma-BL) using 1e,h,i-(BuOH)-Bu-n catalyst systems afforded negligible amount of polymers under the similar conditions. (C) 2008 Elsevier B.V. All rights reserved.