2,4-bis[(2-methylphenyl)imino]pentane | 960281-00-9

• 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: 2,4-bis[(2-methylphenyl)imino]pentane
• 英文别名: 2-methyl-N-[4-(2-methylphenyl)iminopent-2-en-2-yl]aniline
• CAS: 960281-00-9
• 化学式: C₁₉H₂₂N₂
• 分子量: 278.397
• InChiKey: NODKDTKBLNKCOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-bis[(2-methylphenyl)imino]pentane 在 正丁基锂 作用下， 以 正己烷 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  β-三酮亚胺钴配合物的合成，表征及其在1,3-丁二烯†聚合中的行为

  摘要：

  三个β-三酮亚胺配体（L 1：[CH {CMeN（2,4,6-Me 3 -C 6 H 2）} 2 C（CMe 3 N（2-MeO-C 6 H 4）]，L 2：[CH {CMeN（2,4-Me 2 -C 6 H 3）} 2 C（CMe 3 N（2-MeO-C 6 H 4）]和L 3：[CH {CMeN（2-Me-​​C合成6 H 4）} 2 C（CMe 3 N（2-MeO-C 6 H 4）]），然后用1表征H和13 C { 1 H} NMR光谱，元素分析和电喷雾（ES）MS。β-triketimine钴（II然后通过钴（的相互作用制备）配合物II），溴化与L- 1-3中NaBArF的存在（BARF = [{3,5-（CF 3）2 -C 6 H ^ 3 } 4 B] −）。五坐标二聚体溴化桥键物种[（LCoμ-Br）2 ] [BArF] 2获得了。通过单晶X射线衍射发现配合物的几何形状为略微扭

  DOI：

  10.1039/c4dt02196g
• 作为产物：
  描述：

  乙酰丙酮 、 邻甲苯胺 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 72.0h， 以22%的产率得到2,4-bis[(2-methylphenyl)imino]pentane
  参考文献：
  名称：

  铃木-宫浦交叉偶联涉及杂芳族硼酸酯和叔烷基亲电试剂的铁基催化剂的合理设计。

  摘要：

  描述了使用合理设计的β-二酮基配体支撑的铁基催化剂，各种烷基卤化物与未活化的芳基硼酸酯之间的Suzuki-Miyaura交叉偶联反应。较高的催化剂活性导致较宽的底物范围，其中包括叔烷基卤化物和杂芳族硼酸酯。机理实验表明，铁基催化剂得益于β-二酮基配体支持低配位和高还原性铁酰胺中间体的倾向，这对于实现铃木-宫浦交叉偶联反应所需的过渡金属步骤非常有效。

  DOI：

  10.1002/anie.201914315

文献信息

• A Comparative Study on the Reactivity of Tris‐β‐Diketiminate Ytterbium Complexes: Steric Effect of β‐Diketiminato Ligands
  作者：Rui Jiao、Mingqiang Xue、Xiaodong Shen、Yong Zhang、Yingming Yao、Qi Shen

  DOI：10.1002/ejic.201000156

  日期：2010.6

  tris-β-diketiminate ytterbium complexes with the general formula [YbL 3 ] L = [N(C 6 H 5 )C(Me)] 2 CH - , L H (1); [N(4-MeC 6 H 4 )C(Me)] 2 CH - , L 4-Me (2), and [N(2-MeC 6 H 4 )-C(Me)] 2 CH - , L 2-Me (3)) were synthesized and structurally characterized. All complexes have longer Yb-N bond lengths than other YbL-containing derivatives, and complex 3 has the longest average Yb-N bond length. A comparative study

  一系列具有通式 [YbL 3 ] L = [N(C 6 H 5 )C(Me)] 2 CH - , LH (1) 的三-β-二酮亚胺镱配合物；[N(4-MeC 6 H 4 )C(Me)] 2 CH - , L 4-Me (2), 和 [N(2-MeC 6 H 4 )-C(Me)] 2 CH - , L 2 -Me (3)) 被合成和结构表征。所有配合物的 Yb-N 键长都比其他含 YbL 的衍生物长，配合物 3 的平均 Yb-N 键长最长。对配合物1-3反应性的比较研究表明，配合物3是ε-己内酯和L-丙交酯聚合以及胺加成碳二亚胺的高活性催化剂，而配合物1和2都是在相同条件下几乎不活动。活性序列与Yb-N键的距离一致，
• Bis(β‐diketiminato) lanthanide amides: synthesis, structure and catalysis for the polymerization of <scp>l</scp> ‐lactide and ε‐caprolactone
  作者：Yu Zheng、Rui Jiao、Xiao‐dong Shen、Ming‐qiang Xue、Ying‐ming Yao、Yong Zhang、Qi Shen

  DOI：10.1002/aoc.3150

  日期：2014.6

  complexes stabilized by two L2‐Me ligands, (L2‐Me)2LnNH(2,6‐iPr2C6H3) (L2‐Me = [N(2‐MeC6H4)C(Me)]2CH)−; Ln = Y (5), Yb (6)), were also synthesized by the latter route. Complexes 1, 2, 3, 4, 5, 6 were fully characterized, including X‐ray crystal structure analyses. Complexes 1, 2, 3, 4, 5, 6 are isostructural. The central metal in each complex is ligated by two β‐diketiminato ligands and one amido group

  氯化物（L 2,6-iPr2 Ph）2 LnCl（L 2,6-iPr2 Ph  = [（2,6- i Pr 2 C 6 H 3）NC（Me）CHC（Me）N（C 6 H 5）] -）1当量。NaNH（2,6- i Pr 2 C 6 H 3）生成单酰胺（L 2,6-iPr2 Ph）2 LnNH（2,6- i Pr 2 C 6 H 3）（Ln = Y（1）， Yb（2））。无水LnCl 3与2当量反应。溶于NaL 2,6-iPr2 Ph在THF中的溶液，然后用1当量的溶液处理。的NaNH（2,6‐ i Pr 2 C 6 H 3）给出类似物（L 2,6‐iPr2 Ph）2 LnNH（2,6‐ i Pr 2 C 6 H 3）（Ln = Sm（3） ，Nd（4））。由两个L 2-Me配体（L 2-Me）2 LnNH（2,6 - i Pr 2 C稳定化的两个单酰胺基络合物6 H 3）（L 2‐Me  =
• Synthesis and characterization of Bis(β‐diketiminato) rare‐earth amido complexes, their activity for catalytic addition of amines to carbodiimides
  作者：Yu Zheng、Shuai Zhou、Xu Zhu、Lingxia Cai、Yubiao Hong、Mingqiang Xue

  DOI：10.1016/j.jorganchem.2022.122454

  日期：2022.10

  anhydrous RECl3 (RE = Sm, Nd) with 2 equiv. of NaL2-Me (L2-Me = [N(2-MeC6H4)C(Me)]2CH−) afforded the dimeric chlorides [Sm(L2-Me)2(μ-Cl)]2 (1) and [Nd(L2-Me)2(μ-Cl)]2 (2). Salt metathesis reactions between chloride complexes and NaN(SiMe3)2 in THF yielded a series of bis(β-diketiminato) rare-earth amido complexes RE(L2-Me)2[N(SiMe3)2] (RE = Sm (3), Nd (4), Yb (5), Y (6), Pr (7)). Complexes 1−7 were fully

  无水 RECl 3 (RE = Sm, Nd) 与 2 equiv 的反应。NaL 2-Me (L 2-Me  = [N(2-MEC 6 H 4 )C(Me)] 2 CH - ) 得到二聚氯化物 [Sm(L 2-Me ) 2 (μ-Cl)] 2 ( 1 )和[Nd(L 2-Me ) 2 (μ-Cl)] 2 ( 2 )。氯化物配合物与NaN(SiMe 3 ) 2在THF中的盐复分解反应产生一系列双(β-二酮亚胺)稀土酰胺配合物RE(L 2-Me ) 2 [N(SiMe3 ) 2 ] (RE = Sm ( 3 ), Nd ( 4 ), Yb ( 5 ), Y ( 6 ), Pr ( 7 ))。配合物1-7的特征包括 X 射线单晶结构分析。配合物3-7可以作为有效的预催化剂，将胺催化加成碳二亚胺，得到多取代的胍。催化活性受稀土金属的影响，其活性序列为 Y ( 6 ) ∼ Yb ( 5 ) < Pr
• Bis(β-diketiminate) Rare-Earth-Metal Borohydrides: Syntheses, Structures, and Catalysis for the Polymerizations of <scp>l</scp>-Lactide, ε-Caprolactone, and Methyl Methacrylate
  作者：Xiaodong Shen、Mingqiang Xue、Rui Jiao、Yong Ma、Yong Zhang、Qi Shen

  DOI：10.1021/om3005299

  日期：2012.9.10

  Reaction of LnCl(3) (Ln = Y, Yb) with 2 equiv of NaLPh2,6-ipr2 (L-Ph(2,6-ipr2) = [(2,6-(Pr2C6H3)-Pr-i)NC(Me)CHC(Me)N(C6H5)](-)) afforded the chlorides (L-Ph(2,6-ipr2))(2)YCl (1) and (L-Ph(2,6-ipr2))(2)YbCl (2). Crystal structure analysis revealed 2 to be the unsolvated monomer. Treatment of the chlorides 1 and 2 with NaBH4 in a 1/1 molar ratio in THF led to the preparation of the monoborohydrides (L-Ph(2,6-ipr2))(2)LnBH(4) (Ln = Y (3), Yb (4)) in good yields. Reaction of LnCl(3) (Ln = Y, Yb) with 2 equiv of NaL2-Me (L2-Me = [N(2-MeC6H4)C(Me)](2)CH-) in THF, followed by treatment with 1 equiv of NaBH4, afforded the monoborohydrides (L2-Me)(2)LnBH(4) (Ln = Y (5), Yb (6)). Complexes 3-6 were fully characterized, including X-ray crystal structure analyses. Complexes 3-6 are isostructural. The central metal in each complex is ligated by two beta-diketiminate ligands and one eta(3)-BH4- group in a distorted trigonal bipyramid. Complexes 3-6 were found to be highly active in the ring-opening polymerization of L-lactide (L-LA) and epsilon-caprolactone (epsilon-CL) to give polymers with relatively narrow molar mass distributions. The activity depends on both the central metal and the ligand (Y > Yb and L-Ph(2,6-ipr2) > L2-Me). The best control over the molar mass was. found for complex 6. The M-n(obsd) values (M-n = the number-average molar mass) of the resulting PCL are in good agreement with M-n(calcd), with a ratio of monomer to 6 of up to 1000. The polymerization kinetics of L-LA in THF at 20 degrees C by complex 6 displays a first-order dependence on the monomer concentration. Notably, the binary 6/(PrOH)-Pr-i system exhibited an "immortal" nature and proved able to quantitatively convert 10 000 equiv of L-LA with up to 200 equiv of (PrOH)-Pr-i per metal initiator. All the obtained PLAs showed monomodal, narrow distributions (M-w/M-n = 1.06-1.11), with the M-n values decreasing proportionally with an increasing amount of (PrOH)-Pr-i. Complex 4 can also initiate the polymerization of methyl methacrylate (MMA) at -40 degrees C with high activity, affording the PMMA with 83.3% syndiotacticity.